A Man’s Guide to Boots and Shoes

by Antonio on March 1, 2011 · 136 comments

in Dress & Grooming, Shoes

Over 70 years ago, archeologist Luther Cressman discovered perhaps the world’s oldest footwear in Central Oregon.  The sandals were dated to be 10,000 years old, and from the pictures I’ve seen, were made with intricate weaves that indicated they were not only functional, but also stylish in design.  From our tribal days to modern times, men have searched for and valued footwear that both looked good and got the job done.

Luther-Cressman-Sandals

Luther Cressman and the sandals that he discovered in central Oregon.

The goal of this article is to give you an overview of a man’s options when it comes to footwear.  I’m not going to try to sell the idea that you need a pair of shoes for every occasion, but I would like to expose you to the concept that quality footwear that fits well is a worthy investment, and that the right shoes for the right situation can substantially elevate your personal style and comfort.

Why care about your shoes?

A man should care about his footwear if for no other reason than the fact that it constitutes the very foundation he stands upon.  In an average day, you’ll ask your shoes to absorb the force of your weight 3000+ times; a poor choice here can lead to not only discomfort but injury one step at a time, especially if you select shoes that inhibit your body’s natural gait and cushioning system.

Andy Dufresne was right about everything, except this: People do notice a man’s shoes.

Then there is the appearance aspect. Separate from the rest of your clothing, shoes are a visual endpoint and receive a disproportional amount of attention; despite covering only 5% of your body they can make-up more than 30% of the visual judgement we make when sizing up a stranger.

Ideally you want to choose footwear that is both functional and stylish–by following these footwear selection principles this goal can be easily achieved.

Four Footwear Rules

1st – Wear the right shoe for the occasion – this is the most common mistake I see men make when it comes to footwear.  Running shoes have a purpose; they protect your feet while running.  Steel toe work boots have a purpose; they protect your feet while working.  And wearing these shoes outside their prescribed function is fine as long as they are still appropriate; however, many of us take this to an extreme and have abandoned the middle ground between formal and ultra-casual.

2nd – Invest in quality - Not every man can afford to spend hundreds of dollars on his shoes; however, many of those who can instead choose to waste money elsewhere and buy new inferior shoes every few years.  This is never a winning strategy, as low quality footwear is held together with glue and made with cheap raw materials such as cardboard and paper that does not age well. You can save money in the long term by buying more expensive shoes that last for decades.

I want to expand on this point just a bit more; to buy quality, many men will have to save and budget for the purchase.  This isn’t a bad thing–in fact, it can instill a respect for the quality of the product and encourage you to take better care of them when purchased.

And don’t forget the thrifting option.  Assuming you can find a pair of quality shoes that fit you from Allen Edmonds, Alden, or another manufacturer, you can send them back and take advantage of their re-crafting and re-soling service.  A new pair of shoes for a fraction of the cost, rebuilt to serve you for 20 years.

3rd – Never sacrifice proper fit and comfort - buy the right shoe size, even if this means paying a bit more and purchasing your shoes at a brick and mortar shop vs. going the tax free/lowest price online route.  Actually, this isn’t a bad deal, especially if you support a local small business that can really give you solid guidance as to what styles are available and show you how to take care of your purchase.

Brannock-device-patent-image

Use a Brannock device to measure your foot if you’re not sure about your size.

Another fit issue is paying attention to shoe width.  Men with extremely wide or narrow feet learn about this from an early age, but many men who would be better served by just a slightly wider or narrow shoe never discover their perfect size because the normal sizes do an OK job.   I challenge you to take the time to find the right size…..you’d be surprised about what you’ve been missing, especially if you spend quite a bit of time on your feet.  Look for variations in arch support and toe structure as well.

4th – Take care of your shoes - We’ve written about this extensively here at the Art of Manliness.  Learn how to waterproof your shoes in this classic article and then learn how to shine your shoes here.

In addition, rotate through a few pairs to allow them to dry between wearing and ALWAYS use wood shoe trees that will quickly soak up perspiration.  This is especially important for leather shoes, as the interior of a dress shoe has often not gone through the harsh chemical treatment of the upper and is more susceptible to rot.

Common Footwear Terminology

shoe diagram

  1. Sole – This is commonly referred to as the bottom part of the shoe or boot and can be further divided into the outer sole, mid-sole, and insole depending on the type and quality of the shoe being discussed.
  2. Upper – A general term that refers to the part of the shoe above the sole.
  3. Brogueing – a form of ornamentation in which tiny holes are carved into the shoe’s leather.  An important point to remember is that the more decoration on a shoe the less formal it becomes.
  4. Open Lacing – One of the two lacing systems used in oxford shoes, the open lacing system delineates the shoe in question to be a blucher. The shoe’s tongue and vamp (parts of the upper that cover the top of the foot) are cut in one piece with an open throat.
  5. Insole – As mentioned above, a subsection of the general term sole, the inner sole is the layer of the sole upon which the foot rests.  A quality insole can mean the difference between a shoe that will last 5 years and one that will last 25.
  6. Heel – The back portion of the shoe that comes into direct contact with the ground and gives elevation to the foot when the shoe is worn.  Heels are often built from 2 to 4 pieces of leather called lifts and reinforced with rubber or metal.
  7. Laces – The choice is usually round or ribbon, with round having the advantage of being stronger  and more formal thanks to their core while ribbon laces come in a variety of colors and are more elastic and are thus a good choice for athletic shoes or hiking boots.

Men’s Footwear Type Overview

Dress Shoes

Oxfords are lace-up shoes built to be worn below a man’s ankle.  They are commonly divided into balmorals and bluchers due to the difference in their lacing systems.  Balmorals are commonly referred to simply as “oxfords,” while bluchers are referred to as derbys but rarely oxfords; all of this leads to confusion naturally.  So for simplicity’s sake, I will refer to balmorals as balmoral oxfords and bluchers as bluchers.

Balmoral oxfords use a closed lacing system and are normally styled more simply than bluchers.  Thus balmoral oxfords are classified as the dressier of the two; they are best worn with suits and formal wear.  I advise every man to own a classic pair of balmoral oxfords to wear with his 2-piece suit.

Classic-Oxford-English-Made

Classic English Made Oxford Balmoral

Bluchers usually come in a much wider range of styles and colors, and a conservative pair can be worn with a suit and for many men is their go-to pair of shoes to wear with the suits in their wardrobe.  That being said, bluchers that utilize brogueing, a split toe, or color combinations look best with more casual clothing.

Slip-ons are not oxfords as they do not use laces; by design they are less formal although if conservatively styled they can and have been worn with suits. However, they are generally more at home with grey flannel trousers and a sport jacket.   Moccasins, monk straps, and tassel loafers are just a few of the more popular options available.  Many of the styles you’ll find in the slip-on category could have been classified below as casual footwear; this just highlights the fact that there are very few hard lines when dividing items like this.  I personally love slip-ons, as they make travel so much easier when you have to go through 6 metal detectors over a 24 hour period.

For a more in-depth overview of men’s dress shoes click here, and for a chart overview of men’s dress shoes click here.

Casual Footwear

Saddle Shoes – A casual oxford shoe, the saddle shoe is distinctive because it utilizes a layer of leather over the instep that is normally a different color than the rest of the shoe, thus classifying it as a casual but stylish choice.

Image from The Shoe Buff

Boat Shoes or Top Siders – Made to be worn on a boat to prevent slipping, they have migrated from the docks of Boston to the wardrobes of men looking for a summer shoe that can be worn without socks. Available in a variety of colors, the men’s boat shoe comes in a moccasin style and is only for warm weather.

Sperry-TopsiderLeather Laced – Heavy Sole – The two most well known shoes in this category are Dr. Martens and Sketchers.  Ranging from $40 to $200, these shoes vary in their build quality but are consistently casual in nature due to their large rubber soles and overall heavy appearance.  Relying on glue and being manufactured with shoddy materials (Dr. Martens moved the production of most of their shoes and boots to China several years ago), these shoes fill a niche but are not long term value pieces and are best avoided by a man looking to build a serious wardrobe.  I would say their one redeeming quality is their ability to withstand poor weather conditions, but if that’s your goal, then you should consider a quality pair of boots.

 

Canvas Shoes – Sneakers come in a wide variety of styles and colors, however the rules of wearing them outside of the gym are universal.  When clean and situation appropriate, they work well with chinos, jeans, and shorts.

converse-allstar

Converse – what more is there to say about this classic sneaker.

Leather Loafer – separate from the slip-on leather dress loafers above, these slip-on loafers are built with heavier rubber soles and more casual uppers to include leather imitations.  Their styles are wide and range, but the purpose of their construction is to fill the void between canvas shoes and dress shoes while maximizing comfort at a value price.  In the US I feel the manufacturer Clark’s does an admirable job putting out a solid shoe; outside the US, look for Ecco and their wide range of casual and comfortable footwear.

Sandals – One of man’s earliest forms of footwear, sandals continue to serve as a solid choice for protecting the bottom of our feet while allowing maximum air circulation to the upper portion.

Clogs, Flip Flops, and Crocs –  I was told that if you can’t say something nice, don’t say anything at all.  So I am silent.

Athletic Shoes

Running shoes, basketball shoes, tennis shoes–you would think the occasions for which these were meant to be worn would be clear.  Yet we persist in wearing our white running shoes everywhere, declaring it a right because they are comfortable.  I counter this argument by saying that many of us are too lazy to take the time to think outside the box and select a casual shoe that looks sharp and is comfortable. They definitely exist.

Boots

Work Boots – There’s a cobbler I use in Green Bay whose shelves are lined with two types of footwear.  High end dress shoes that need to be conditioned and shined, and work boots that have gone through a beating and need new soles.  Like a pick-up truck that works hard and simply needs an oil change and new tires, quality work boots last forever and help you get the job done. Any man that works 14 hour days in construction learns at an early age that spending a bit more for quality boots is an investment in how his body will feel that weekend.  And as mentioned before, solidly built work boots can be re-soled, while cheap boots that are made with glue and inferior materials not only fail under heavy usage but cannot be fixed as they were designed to be disposable.

Caterpillar-2nd-Shift-Steel-Toe-Boot

Caterpillar makes an excellent work boot – notice the stitched sole.

Hiking Boots – Hiking boots are designed to support the ankles, provide cushion, and protect from the elements, while still being light enough to not impede stamina.  Boots that meet all this criteria are an outdoorsman’s delight; those that fail can turn a trip into a painful lesson of why quality matters.

Western Boots – Growing up in West Texas, I have a special place in my heart for western boots.  Functionally, they serve the purpose of keeping a man in his saddle, protecting him from the terrain, and if taken care of, they can last as long as his horse.  But that’s the issue–most of us don’t require this functionality and wrestle with the issue of whether or not we deserve to wear something so idealized by our culture.

Personally I feel a man can pull off western boots without being a cowboy – the key is being comfortable and confident in them.  And avoid flashy or brightly colored boots unless they have a special meaning or you crafted them yourself, otherwise you’ll look like a clown.

Lucchese-Cowboy-Collection-stonewashed-lizard-boots

Lucchese makes an excellent boot. Just make sure to get two of them.


Dress Boots – This includes a wide variety of styles and manufacturers, from Red Wing’s Heritage collection to the classic Chelsea made famous by the Beatles.  While many are built to withstand the rigors of hiking and working, they are more often than not worn for their style, not their function.

The Wolverine 1,000 mile boot. Made in the USA in a 300 step process. Brett’s an owner and a big fan.

A Note on Custom Made Shoes

If you’ve made it this far into the article, I take it you like to read about shoes.  So let’s turn it up a notch and briefly discuss the option of bespoke boots and shoes.  It’s not for every man, but I feel a discussion on footwear would be incomplete without it.

All shoes used to be custom; mass manufactured footwear that’s comfortable is a modern luxury.  Crafted one at a time, a man’s status (much more than today) was determined by what he could afford to wear on his feet.   Today the art of hand making footwear rests with a small number of artisans scattered across the globe.

First, when commissioning a pair of bespoke shoes be prepared to pay.  Handcrafted shoes are expensive because modern artisans only use the finest materials, there are very few of them that do this type of work, and it’s very time intensive.  And believe it or not, demand is incredibly high–waitlists of 2 to 3 years are not uncommon.

Once the process begins, a bespoke shoemaker will first carefully examine your foot.  He’ll consult with you on the best style and design for your body and professional needs, then build lasts (replicas of your feet) which the shoe will be built around.

After this, the artisan performs his magic.  He’ll carefully select the right materials and then cut the insole, prepare the upper, prepare and then stitch the welt, sole the shoe, attach the cork filling and insert a steel shank spring, stitch on the outsole, build the heel, and then finish everything with final shaping and ornamentation.

This intensive process takes most shoemakers approximately 10 weeks for a single pair.  If you’re looking for a great read on the subject, pick-up the book Handmade Shoes for Men.  If you’re looking at custom shoes, consider speaking with Steven over at Leffot. But be careful about reading his men’s shoe blog: you might get sucked in for hours.

Button-dress-shoe

Footwear like this has to be made for you……..

A Man’s Guide to Footwear – In Conclusion

As previously stated, my goal here was to give you an overview of your options.  Each type of footwear we discussed has its own history and could easily have been its own article.  In fact, I’ll leave you with that.  What piece of footwear would you like to see us write more about?

See you in the comments!

 

Written by
Antonio Centeno
President, A Tailored Suit
Founder, Real Men Real Style

{ 136 comments… read them below or add one }

1 Alex Shirley March 1, 2011 at 8:22 pm

Antonio, yet another interesting and informative post!
If you read the comments, I have always been hoping that you or Brett would write a piece on jeans (work and casual), an article of clothing deeply rooted in the man of Americana! Just an idea. Hope to see a new one.

2 Brett March 1, 2011 at 8:57 pm

Let’s hear more about Western boots. I also support the jeans idea.

3 Peter Samuel March 1, 2011 at 9:29 pm

How can you go without mentioning the desert boot (Clarks, for example)? They’re classic.

4 Eian March 1, 2011 at 10:21 pm

I, like many other people have become enamored with the barefoot trend. Currently, my favorite footwear (besides the naked foot) is my pair of Vibram FiveFingers KSOs. While technically running shoes, I’ve taken to wearing them around metropolitan Manhattan since they cause less discomfort than my old go-to-shoe, the classic Adidas shell-top. I’d love to hear your take on these quirky shoes.

5 Chris March 1, 2011 at 10:42 pm

I’d like to read more about bespoke shoes and boots (what to look for, who makes them and so on). I’d also like to read more about dress boots and chukkas. And I third the jeans idea.

6 Jordan March 1, 2011 at 10:49 pm

I for one can vouch for the importance of buying a quality boot. This summer i started my seasonal job at Philmont scout ranch (which would be a great article to write about, anyone who is a scout will have their eyes brighten if you mention the words). I worked there as a conservationist where i did a whole lot of hard work, and really put in hours on my books, basically living as a mountain man. Before i left, i bought a pair of boots that were one of the less expensive ones. I learned very quickly that they were not the right choice as i had to glue and tape them together the whole summer.

7 Greg March 1, 2011 at 10:54 pm

I where boots all the time because they protect your feet the best. They may not be the most stylish but are useful, I would like to here more about Western boots. I would hate to here more about desert boots, due to my time in Iraq I would say I would never where those things in the sand. Thanks for the info man.

8 Paul March 1, 2011 at 10:54 pm

Good article, but I would have liked more information about boots.

My go to shoes are actually boots – either Chelsea or chukka (I’m not sure if you use that term in the states, but they look a little like the ‘wolverine’ above, but more dressy and formal).
I like these as they a) look great and b) feel a bit more secure than shoes.

I also agree about desert boots. Less formal of course, but you can wear them with jeans or a summer suit, and can even get away with shorts.

My general rule for clothing is ‘If Indiana Jones would wear it, it’s probably ok’.

9 James Fife March 1, 2011 at 11:08 pm

Thanks for another great article. I’m updating my wardrobe because of a move to the city, and I was quite a bit short on footwear knowledge. As it is coming into Autumn here in Australia looking over the sweater article again was quite helpful.

One thing that I really wanted to ask was what British and Italian shoemakers would you recommend? They seem much more available over here.

10 Mark Petersen March 1, 2011 at 11:14 pm

Good article. My dad is a shoe whore in his own right and knows a ton about them so I’ve heard lots about the maintenance of shoes.

I’d like to hear more about dress boots. I’ve been curious about them and find they make a statement about the man who wears them. Every man I’ve ever seen wear them has been a man I well respected.

11 James Fife March 1, 2011 at 11:34 pm

I should say that the sweater article was *also* quite helpful, as written it seems like the sweater article was helpful because it had information on shoes.

12 Nic B. March 2, 2011 at 12:21 am

http://www.fluevog.com/ is a great place for unique shoe and boot designs. For those looking for intriguing and eye-catching footwear, without wanting to shell out the money for custom shoes. They also have great customer service and the staff have always been personable and generous (at least in Vancouver, B.C.).

13 Adam Waerzeggers March 2, 2011 at 12:34 am

Hey- this topic couldn’t have come at a better time…
I’m an engineering student and this summer I start an Internship/Co-Op and it is required that I wear steel toed shoes/boots, even though I’ll be working primarily in an office. Does anyone have any suggestions as to what is common for engineers or just professionals in general to wear on their feet (as far as steel toe goes)?

14 Nic B. March 2, 2011 at 12:46 am

Hey Adam.

A place like Mark’s Work Warehouse or any ‘blue-collar’ clothes store like that should have a nice big selection of steel-toed boots. Since you’re going to be wearing them all day though, don’t skimp on comfort. The first pair of steelies I ever bought were about a half-size too big, but a bit cheaper. Really, really poor decision. That being said, you should be able to find a pair that would be appropriate with office slacks without having to spend more than $150 (especially if you find a good sale).

15 Adam Waerzeggers March 2, 2011 at 12:58 am

Thanks Nic!

I’m actually going to be reimbursed partially for having to buy the shoes specifically for work, so I think I can afford to be a little on the expensive side in order to get a nice comfy pair of kicks. Art of Manliness = Art of Godliness

16 Irenaeus G. Saintonge March 2, 2011 at 2:05 am

I’d love to see a further piece of men’s boots. Hiking boots would be great, and I’d love to read about that, but even more interesting to me is boots that a guy from, for instance, Calgary Alberta, where temperatures of -40 Celsius aren’t uncommon, could wear to the office or even to an important job interview or to Church, and not look like he’d just thrown on his Sorel’s.
Basically, an article about things like those Wolverine’s up there, and footwear similar to it.

17 Lars-B.I March 2, 2011 at 4:45 am

Nice written article.
Im one of those who’s wearing Boots, Dr Martens style. (not that brand though)
To me that kind of shoes is both comfortable and practical for their versatile purpose. As long as you take care of them, and find a manufactor with good quality on their boots. those can litterally last forever. The pair im using now, i have had for the last two or three years. and theyre still as new as when they left the shop.
Since i live in the middle of nowhere, in the northern parts of Sweden, I need shoes that can handle most of the things i will expose them to. (snow, dirt, the woods, water and so on)

18 Robbo March 2, 2011 at 4:47 am

You trash jandals (flip flops) in this article, much to my chagrin. In the summer time I wear nothing but. They’re just so convenient, if I’m going to the swimming hole or round to a friend’s place I just throw my feet into them and I’m ready to go. No fussing around with laces or straps. In fact, you don’t have to use your hands at all! It might just be a cultural thing, but where I’m from you like a fool if you don’t wear jandals in the summer time.

I agree with you on work boots though, I bought a cheap pair for my work and they’re falling apart after just a year. And they don’t even get a hard time. Quality is very important.

19 rj arena March 2, 2011 at 5:36 am

I have a wide foot that is flat, so I have had to invest in good shoes or there will be pain. Since the they are expensive, I must take care of them. One of the best ways I have found to do this is very simple and I do it every day, I use a shoe/boot dryer. My shoes are now odor free and last much longer than before(I also try when possible to rotate what I wear). In my experience moisture is the enemy- hot sweaty shoes simply rot over time, trying them everyday on a shoe/ boot dryer is the solution.There is an added bonus- putting on a dry warm shoe on a cold morning. I also once a week inspect what I have worn over the last few days and pull out my shoe kit and give them a proper cleaning and polish. I does make a difference!

20 Murad March 2, 2011 at 7:11 am

Great info!

However i have one single complaint, and it’s not about this article in particular but about AoM apparel articles in general.

Not all men are built equal in physical appearance therefore i’d much prefer to see more tactical definitions, ie if you are a tall person you should prefer longer shoes etc etc and this shouldn’t be limited to shoes at all, like i’ve said i’d love to read about anything from spectacles for your face shape to winter clothing for your body type and what not.

Hope i made myself clear,

Regards,
Murad

21 Perry Randall March 2, 2011 at 7:39 am

This is a wonderful article. Thank you.

What I’d like to see is not so much different shoes (although jump boots are conspicuously absent) so much as how to use the shoe to complete one’s overall look. As an example:

How would one wear jeans with Oxfords?
Why are dress boots considered a more casual choice?

Things of this nature.

Regards,

Perry

22 kelly March 2, 2011 at 8:15 am

You have got to be kidding me! Caterpillar and Wolverine? Did you read this crap somewhere? I wear steel toe boots everyday at my workplace,which is in Construction and no one who is a professional in my field would be caught dead wearing wolverine or caterpillar boots. They are very inferior to Redwing or Thorougood boots. Redwing or Thorougood boots are made in the USA,,made from better quality leather,better stitching,and will last alot longer than those cheap china made boots that you recomended. I have been in the construction industry for 19 years and feel well qualified to speak on behalf of these boot companies, I like your articles but now wonder where you get your information and if I should believe anything else you print.

23 Michael J. Long March 2, 2011 at 8:15 am

Great article, I myself were Red Wings for work,play and for casual wear,not much for gym shoes. I also bought a pair of Edmond Allen’s for dress,not that I get dressed up very often ( I’m a carpenter but My father always instilled that shoes are worth what you pay for.) Love your info on all the stuff you guy’s write about keep it up and thank’s and have a great day.
Michael J. Long

24 Ryan March 2, 2011 at 8:15 am

“They were designed to be disposable.”

This is something that I’ve been trying to avoid in my fashion purchases, but it poses quite a few challenges. For me, this inclination came after I read William Gibson’s Zero History. By the end of the book, one of the designers explains that a button-down was actually better made a century ago in comparison to today’s factory-made shirts. I get the feeling that this trend is true for many of our products, including food. Unfortunately, quality costs, so you really have to research what you’re buying. Also: if you’re going to wear quality, you’ll wear it for a long time, so avoid fads. That means even more research.

Thanks for the heads up on shoes,
Ryan

25 deborah carre March 2, 2011 at 8:53 am

For those of you enraptured by the idea of bespoke and would like to know more about the actual handsewn making craft then visit our blog carreducker.blogspot.com which offers a rare inisght into the craft. As does Marcel from Koronya’s blog.

Happy reading and it’s great to see so much consideration going into men’s footwear.

26 DR March 2, 2011 at 9:13 am

There’s something amazingly classic about Oxford toes, they really can dress up anything. The dress boot pictured also gives off such a pleasing aesthetic!

DR

27 dango March 2, 2011 at 9:20 am

great job, anthony.

thankfully, footwear is one of those areas where you usually get what you pay for… price and brand generally are a reasonable indicator of quality. That is helpful, as the list of tricky decisions is reduced to style and fit.

a suggestion for when a followup boot article might come out….include a paragraph or two on the proper selection of pant cut that matches the varying types of boots.

28 Preston March 2, 2011 at 9:26 am

I would also like to hear a few more people’s take on Vibram Five Fingers shoes. I have owned a pair for about three years that I run in, and I think they are great; but I feel a little foolish wearing them as a casual everyday shoe. They truly are the most comfortable shoes I have ever owned. Wearing them really does allow the foot to mimic the movement and flexability of walking barefoot. They only problem is that they look goofy as hell when worn outside of an athletic setting.

29 Russ March 2, 2011 at 10:10 am

You missed the most important part. Its called the “last”. It is measured by a brannock device, and is the measurement from your heel to the ball of your foot. Traditionally different brands have different lasts. You can kind of bet that if you find comfortable shoes of a given make it is that the “last dimension” is right for you and probably you should look for that manufacturer next time you want to buy shoes.

30 Kevin T. Keith March 2, 2011 at 10:13 am

Thanks for a useful and interesting article.

I feel silly having to ask, but could you clear up one thing: what is the difference between “open” and “closed” lacing for Oxfords? And does this relate to a difference in the construction of the shoes, or just the way the laces are put in?

Thanks.

31 TrevorB March 2, 2011 at 10:14 am

You seem to have forgotten the Chaco line of sandals, in some circles this shoe is worn all summer long no matter the dress attire. They are by far the best investment a man can make when it comes to casual outdoorsy summer footware, you have never felt true freedom without a chaco.

32 Ryan Grimm March 2, 2011 at 10:23 am

I most heartily recommend the Red Wing Heritage Collection, as well as their Work Boots…I’ve had Red WIngs for over 25 years, including the first pair I’d bought…and since had Red Wing rebuild.
I rotate between my 2nd and 3rd pairs to rest and dry them….good practice.
Note that the Heritage Collection boots are not normally stocked in East Coast stores, but are available. Some styles MAY be kept in stock in SOME stores, just ask your local store…I love my boots!

33 Cameron T. March 2, 2011 at 10:42 am

I’d like more clarification on the different lacing styles mentioned. First I’ve heard about anything but the usual crossed-laced style.

34 Andrew March 2, 2011 at 10:46 am

I happen to sell boots, so here are some of the basics for the people who were asking for more about them:

First of all, pull on boots will not fit the same as shoes that lace up. You want them to be a little snug when they’re new, especially across the top of your foot because the leather will stretch as you get them broken in.

I also get a lot of people who don’t wear boots much who are concerned that their heels are slipping out of the back. Because of the way boots are made, it’s perfectly normal for your heel to slip up and down about a quarter inch to a half inch. That slip goes away once you break them in.

Also, know what kind of sole and heel you want. A western heel (also called a riding heel) is taller and designed for riding horses, though some people prefer them for other reasons, such as they feel it’s dressier or that it gives a more “authentic” western look or because it’s just more comfortable to them. Roper heels (also called walking heels) are shorter and more common among people who don’t necessarily ride but want something they can work in or wear for dress.

There are three kinds of soles: leather, rubber or crepe. Crepe soles have become increasingly rare, but some people prefer them because the softness of the sole is more comfortable to them. I’ve never had a pair of crepes but they don’t seem very durable to me. Leather soles are generally considered to be dressier, and are preferred for riding because they are easier to slide in and out of a stirrup. They are also preferred for people who wear them to go dancing. Just be careful on snow and ice. Those soles don’t get a lot of traction and you could slip pretty easily. Rubber soles are mainly for work books or people who are concerned about slipping with leather soles.

Also, boot sizes are not consistent. They run differently across brands and sometimes even across different styles made by the same brand. I would never buy a pair of boots without actually trying them on. To find your size, start about half a size smaller than you would wear for shoes and go from there until you find something that feels good on your foot.

35 Jordan March 2, 2011 at 10:55 am

For those asking about flip flops, VFF, etc – Yes they are functional and comfortable but they sure aren’t stylish. Wear them for their intended purpose and then ditch them in favor of something more aesthetically pleasing.

36 Joe March 2, 2011 at 11:02 am

Very interesting article. My major problem with footwear is finding sources for quality products. The only choices I have locally are your typical self-serve crap on the shelf stores you find in malls or retail centers. Where the salesperson is the same gal who was working at the jewelry kiosk for Christmas. I prefer to try before I buy, so I’ve hesitated to go the online route.

I miss the days of the old-fashioned shoe store, where the salesman measured your foot, knew the product, and could give you advice. It was in one of these stores that a salesman told me I should avoid loafers because of my high instep. Today, nobody in one of these shoe stores even knows what an instep is, and all they can tell you is that “whatever we have is out on the shelves.”

37 Dave March 2, 2011 at 11:12 am

I just got my recrafted Allen Edmonds back last week. They had four years of occasional use followed by nearly two years of daily use before needing service. They came back looking better than ever (didn’t think that was possible until now) and oh-so comfortable. They claim that, with care, the tops should last long enough for three recraftings. A pair of lesser shoes were quite uncomfortable by comparison when they were pressed back into service for 1-1/2 weeks.

38 BillM March 2, 2011 at 11:45 am

Even though I have been on a horse only once in my life, I love cowboy/western boots, and have owned several pair throughout my life. My current pair are Boulet boots, made in Canada, and purchased at Herbert’s in Toronto. Recently I visited my sister in Plano, Texas (a suburb of Dallas) and purchased a pair of suede Lucchese 1883 boots at Cavender’s (I’m wearing them as I type this). They fit great and I walked all over in them for 10 days with no fatigue whatsoever. Love ‘em!

39 Kevin March 2, 2011 at 11:46 am

A good pair of boots is one of the most comfortable, versatile pieces of footwear you can own. Although I have a pair of leather-soled oxfords for formal occasions (and you should, too) the rest of the time I wear a short boot.

As a pilot, I’m expected to maintain an very conservative professional appearance, but I’m also out performing preflight inspections on icy airport ramps in January. Quality, well-polished black Chelsea boots (with a rubber sole for traction, as Andrew mentioned) are simply the most versatile solution I’ve found – they keep me comfortable both in the cockpit and outdoors, without sacrificing anything in terms of appearance. They can also be slipped on and off easily when necessary to satiate the whims of the TSA.

I’d also like to echo the sentiments of those who are fans of the classic British desert boot. Outside of the workplace, I wear these all the time, and they’re easy to dress up or down as the need arises – mine go everywhere from skeet shooting with my buddies to nice restaurants. Just make sure to keep them clean.

40 Barney A. Bishop March 2, 2011 at 12:04 pm

I’ve always tried to pay close attention to my shoes as they can truly make a difference. A pair of custom made shoes is definitely a dream of mine. Great piece Antonio.

41 Lorin March 2, 2011 at 12:14 pm

Awesome article! I have a pair of quality Oxfords that I bought for my wedding, and they have lasted longer than the marriage.
Lately I got a good deal on a pair of Vasque hiking boots. They were comfortable on the first hike, and even more comfortable when broken in. I would love to see an article on hiking boots, because there are a lot of different styles of hikers, and the good old fashioned rule of “the fewer the stitches on the upper, the better the quality of the boot” still applies today.

42 TR March 2, 2011 at 12:45 pm

Nice post Antonio.

I think we also need to cover the simple act of tying shoelaces. A lot of people do not tie them, for example to make their shoes more like slip ons. This is not very good for your feet because the shoes are too loose. Also, lace length may be important too, depending on the person, if you tie it a certain way you may have too much lace hanging out. I don’t remember this being discussed before.

43 EJPG March 2, 2011 at 1:01 pm

An important article, as so many men’s shoes are falling apart not long after purchase. While looking for quality, also bear fit in mind. I recently spent quite a lot on some Dr Martens boots, which are very uncomfortable as the leather has stretched and there is no padding. # Top Tip = wear the shoes / boots at home for several evenings and return them if any issues arise!!!

44 Michael Dykes March 2, 2011 at 1:04 pm

My boot of choice is a Carhartt pull-up that looks like a cowboy boot and a work boot reproduced. They have a cowboy shape minus the intricate decorations with a work boot’s rounded toe minus the steel.I have had these boots for around 7 years and they still look new thanks to good maintenance. I just looked at the company’s products and found out that they no longer make this model. I have worked in them and have worn them with a good portion of my wardrobe.

45 tim_lebsack March 2, 2011 at 1:21 pm

re: “build lasts (replicas of your feet) which the shoe will be built around.”

Unfortunate that the typical last’s resemblance to the human foot is minimal.
No wonder shoes are often uncomfortable.

46 zack March 2, 2011 at 1:36 pm

I would like to see a write up about telling the difference between quality and just a name. I understand what you mean when you say buy quality and buy it once as opposed to buying cheaper things time and time again…
but how can you tell the difference between something that cost more because of quality and something that cost more because of its name?

47 Darren March 2, 2011 at 2:02 pm

My browser crashed and took my post. This means you get the short version:

1) Kelly is right — Red Wing, Vasque, etc. Good. Caterpillar – junk.
2) Love Filson for hunting boots. Russell if you can afford them.
3) Buy shoes in Europe.

48 Tim R March 2, 2011 at 2:26 pm

Can’t recommend Blundstones enough — they have work boots cut like dress boots, which means durability that also looks decent. I’ve taken my pair through the Scottish highlands, over Corsican mountains, through the streets of Istanbul, and out in the Syrian deserts (at least a couple hundred miles of walking, not to mention thousands via transportation), and there’s still not even a stitch loose. I’m about to take them out on a three-year period of nomadism around the world sans air travel, and have high hopes that they’ll last me through the end.

49 Andrew T March 2, 2011 at 2:40 pm

I’m interested in dress boots. In the winter, boots are a requirement in many places, but no one wants to wear a nice suit with duck boots.

50 kasakka March 2, 2011 at 2:42 pm

No mention of sneakers beyond the Converse type? Something like the Adidas Superstars or Nike Air Force 1s certainly don’t look like all those awful sports shoes. They’re very comfortable, come in a variety of styles and colors to match the rest of your clothing and can be classy and understated.

The Vibram Five Fingers are also worth a mention. Not exactly pretty, but for most athletic activities they’re great. Very good for “barefeet” running and martial arts.

PS. After being in the army, I don’t think I ever want to wear boots again.

51 Cael March 2, 2011 at 4:11 pm

I also would love to see an article about how a man should outfit his wardrobe with jeans.

52 SW March 2, 2011 at 4:12 pm

I would like to hear more about boots in general, but combat boots in particular. (My only experience is with the standard issue ones)

53 Curt March 2, 2011 at 4:17 pm

So I’m looking for a shoe to dress down a pair of brown windowpane dress pants. I was thinking about a brown, non-shiny Doc Marten 3-eye, but I notice you said they’re a poor investment. I do want something lace-up, leather, and non-shiny, something fairly durable and comfortable. Any alternatives? I was also wondering if you had any suggestions for a lightweight Italian loafer breathable enough for summertime that doesn’t cost a thousand dollars. Thanks, for all the good info.

54 Justin March 2, 2011 at 5:08 pm

An article on outfits based off wearing jeans would be great! Most working class guys I know (myself included) prefer to wear jeans. Some advice on what to wear with jeans to still maintain a classy look would be great! As always great info on this site!

55 Jeff March 2, 2011 at 5:26 pm

A man should also own a pair of slippers or moccasins. Minnetonka makes excellent masculine slippers.

56 Jordan March 2, 2011 at 6:38 pm

Great to see an article educating men on the value of quality shoes. As a men’s shoe salesman at the Seattle Nordstrom store, I encounter men on a daily basis who are uninformed and believe the lower the price the better the deal. Not only are bargain priced shoes generally hideous, they will cause you discomfort and fall apart quickly. I tell my customers, “Never go cheap on your bed or your shoes. If you’re not using one, then you’re using the other.”

57 Peter Hernandez March 2, 2011 at 6:48 pm

I second (or whatever number it is now) the article about wearing jeans, but if I was to talk about shoes I’d like to see an article on riding boots in relation to motorcycle (or moped) riding. An article on proper attire for someone who rides a motorcycle to the office would be great. So far it seems a choice between looking tacky or like the member of a motorcycle gang. Some clearing up would be awesome

58 Kory March 2, 2011 at 7:04 pm

Right now Allen Edmonds has a promotion going on, Soles 4 Souls, with the donation of a gently used pair you get a $35 discount upon ordering. The promotion is good at select retailers or online. Check allenedmonds.com for locations.

I just ordered a pair of Minnesota Twins Sandlot deck shoes for the summer. The promotion runs the gambit of their line. Standard shipping is free too!

59 Paul March 2, 2011 at 7:24 pm

As someone who spent 9 years in the military, I can attest to the comfort and quality of a good pair of combat boots. I think they deserved their own mention, as they are a combination of the durability of a work boot with the versatility of a hiking boot.

60 david March 2, 2011 at 7:28 pm

I owned a pair of Caterpillar brand work boots like those pictured and they were the worst boots I have ever owned. Be very sure that those are what you want before buying them. 0 out of 5 stars from me.

61 Eric March 2, 2011 at 10:07 pm

If you, like me, despise dress shoes for their lack of ankle support, look into finding a pair of paratrooper jump boots. Shined up a little, and with a pair of slacks that isn’t too short, they look like oxfords, but you won’t break and ankle if you step wrong.

62 Mike March 2, 2011 at 10:26 pm

I am a firm believer that every man should at least have a pair of wing-tips and a pair of non-glossy penny loafers. These can get you through most occasions. I also enjoy wearing Sperry boat shoes in the summer.

I NEVER wear running shoes for anything other than exercise (not only does it look bad, it wears out the shoe), and being a soldier, I NEVER wear my combat boots with civilian clothes. It kills me every time I see a young Joe walking around in jeans and suede combat boots… looks terrible.

@Justin, a basic guideline for jeans: The darker the jean, the more formal you can make your outfit. Lighter colors and washes are for more casual occasions. You can dress up a pair of dark blue jeans with a collared shirt and a navy blazer. You can also go with the collared shirt and a v-neck sweater; In the case of the sweater, it is a bit more casual so you can go lighter on the denim.

Going along with the jeans, wear an appropriate belt. A braided leather belt is not appropriate for all occasions. If you are going to dress up your jeans, get a dressier looking leather belt (think simple and more glossy).

63 Mike March 2, 2011 at 10:28 pm

I forgot another important issue: socks. Athletic socks are not all occasion appropriate. They belong with your athletic shoes, doing athletics. Step up your game and get some better looking socks.

64 Thad March 2, 2011 at 11:10 pm

Antonio, you know me … always ready to hear more about cowboy boots!

Cheers!

65 Samuel Warren March 3, 2011 at 9:50 am

For casual and dress, you can’t go wrong with ecco shoes! They’re very well built.

66 Ben March 3, 2011 at 10:29 am

Antonio -

Great article. I really like the look of the Dress boots – and they also fit my personality. They look like a great choice for the fall or winter. My question is what do you pair them with? I imagine nice heavy looking slacks with a tweed jacket would work fine – but what else can you pair them with? Both relatively formal (at the office perhaps) and relatively casual on the weekends for instance? Basically, I’m trying to decide if paying significant $ on this item would be a worthwhile investment for me.

Cheers,
Ben

67 Dennis March 3, 2011 at 11:00 am

Last year I purchased steel-toed work boots (your recommended brand). Within one week the soles were uncomfortably bumpy. A cobbler told me the steel reinforcement is folded under the sole and mine was wavy. He could not repair the problem. Is there a method to determine the quality of the steel toe in a boot prior to purchase?

68 Eric March 3, 2011 at 11:37 am

Great article indeed. The 1000 miles shoes are really hot and who doesn’t need at least one pair of Lucchese! Amen on the Balmorals.

A word of warning on the CAT boots: good support and sturdiness, good in the woods on firewood duty, kicking hay etc, but a disaster in oil. Do not wear these in the engine room or turbine test unless you want to break your neck or catch yourself grabbing a hot line. Look in the Redwing line.

I want a picture frame with those Wolverines, can’t get over it.

69 Matt March 3, 2011 at 11:52 am

I’d like to know how to determine what makes a comfortable shoe.
I’m on my feet all day and picked a shoe that is hard soled with a decent cushion insole, or so I thought. My feet and heels are sore everyday now.

70 Eric March 3, 2011 at 12:17 pm

Dennis, if I may. I’ve decided a steel toe has to be comfortable right out of the box. No “breaking in” or “rodage” taken in consideration on the day of purchase, even though the reality is you DO break them in. I do not know what is this brand of which you speak but Redwing has worked very well for me in extreme conditions; my heavier framed colleagues are sold on them as well. These boys are 6’2″ish, 250 and above-ish, hard on tools and clothes and Redwings and Wolverines are majority brands with them. I’m only sz 10, 170lb and my boots last a long time
There is something going on with chinese products: several cobblers have told me there are glues and linings in the chinese boot that render it difficult or impossible to rework.Years ago I tried to resole a pair of non-steeltoe Die Hard wedges that became comfortable as slippers but it was no go.

71 Grown Up Tomboy March 3, 2011 at 2:25 pm

Hey Peter

The solution I use when I’m riding my motorbike to a job is to arrive early and change into appropriate clothing. Loosely roll your trousers and put them in a bike bag with your tie (my husband ruined some ties wearing them whilst riding) and your shoes.

If you want to survive a bike crash, protective gear is the way to go. Good motorbike boots have extra leather over the top of the toes, reflective panels on the heels, and waterproof fastenings (zips/velcro). They don’t look smart to begin with, and don’t stay smart in use. A boot that looks smart won’t stay that way, and may not offer enough protection for accidents.

I’m wondering where Antonio found the DM’s he mentioned, but the Vintage range are still made in England with the original equipment, and may be worth considering.

72 Grown Up Tomboy March 3, 2011 at 2:31 pm

Here’s a link to the Vintage range for US customers.
http://www.drmartens.com/productlist.asp?story=vintage

73 Brett McKay March 3, 2011 at 3:44 pm

@Ben-

I’m not a style expert, but personally I’ve worn my Wolverine 1,000 mile boots with everything from t-shirts to jeans to an outfit just as you described–a tweed coat and heavy slacks, and with everything in-between as well. So they’re really versatile, they look fantastic, feel comfortable, and are just all around awesome.

74 Jeff March 3, 2011 at 4:25 pm

I really appreciate this article as well. It’s a big help.

I will agree with others about Doc Martens – there might be inferior qualitiy ones out there but I’ve never seen them. My first pair of DM shoes lasted me well over ten years – and I wore them nearly everyday. Sure, Docs may not be the answer for everything style wise (I find myself now wanting to distance myself a bit) but they were well worth the money I spent on them.

As far as work boots go I was also surprised to see the Catipillar brand mentioned – I’ve never been too fond of them. Red Wings or Wolverine are what my father swore by – he was in construction for 40 plus years.

75 Angevin March 3, 2011 at 6:19 pm

I disagree that bluchers are ‘dress’ shoes. Bluchers are casual in that one should wear them with a blazer and trousers rather than with suits. Balmorals are for suits and when wearing a suit one is technically dressed up but not formal therefore logically balmorals are dress shoes and bluchers are casual shoes.

76 Angevin March 3, 2011 at 6:21 pm

I should say blazer or sports coat to be precise actually. One can wear bluchers with a blazer or sports coat but not suits hence bluchers are casual shoes.

77 Robert Pruitt March 3, 2011 at 9:58 pm

I am really intrigued by the custom shoes. Any idea on starting price range?

78 Steve March 3, 2011 at 10:04 pm

Glad to see this as I’ve been pondering spending more on a better pair of shoes, but what I was also hoping to see would have been a guide on how to shop for them – that is, how can I tell the difference between a shoe that’s “disposable” and one that can be repaired and will last a while? I gotta assume there’s more to it than price.

79 Angevin March 4, 2011 at 12:48 am

Steve, a simple way to think of it, if you happen to live in the USA, is that Allen Edmonds and Alden are the only way to go and everything else is junk. If you live in Europe things aren’t so simple. Anyway, good shoes are goodyear welted and they are not made with inferior corrected grain leather, which has a plasticky finish to it, but rather with quality calf skin or shell cordovan leather. The calf skin ones will tend to last a decade or decades while the cordovan ones can last a lifetime. Both kinds can be repaired. The best you can get are Alden Shell cordovan they really last a lifetime if you take care of them. Also, I’m not sure about Alden, but Allen Edmonds has a recrafting service that can make your old shoes look brand new : it goes above and beyond simple resoling for a fraction of the cost of brand new shoes. Be prepared to shell out some $$$ though because quality shoes are not cheap but they save you money in the long run since cheaper shoes wear out faster so you buy more of them and that really adds up after a while (accumulation).

80 Angevin March 4, 2011 at 12:59 am

Shoe fact : Shell Cordovan actually comes from the hindquarters of a horse while calf skin obviously comes from a baby cow. The shell cordovan is more durable for what should be obvious reason{s}.

81 P.M.Lawrence March 4, 2011 at 3:13 am

Brogue didn’t start as ornamentation, but as a way to cope with very wet conditions. By having holes all the way through, at least if you couldn’t stop water getting in you could squeeze most of it out again and let air work through to help with any remaining dampness.

82 Matt March 4, 2011 at 3:41 am

Great article but it jogged my memory about something I’ve been looking for, for quite some time.

Awhile ago an acquaintance told me about a company in the states (of America) that made a crazy awesome boot (well… boots) they only did custom made, and they had a superb guarantee including either free or at least cheap restitching. They were supposedly very well known to/specialized in boots for forest fire fighters and outdoorsmen. Unfortunately I can’t remember the name of the company or its website and was hoping that someone here might have an idea as to the company I’m talking about. I’ve tried looking around on Google but I haven’t been able to find anything.

83 Paul March 4, 2011 at 10:08 am

I wholeheartedly agree with the emphasis on quality over quantity. There’s a definite pressure against it though from marketers who like to suggest that you need a different outfit to match each of the different things you do. If unchecked by manly reason and restraint it leads to a sort of manic attempt to outfit your wardrobe for every conceivable eventuality. Result: a huge collection of cheap throwaway items most of which only get used once in a blue moon. Realistically most of us by the time we are in our 30s and 40s have fixed our attention on a few regular pass-times with only the occasional foray into new territory. For me this mostly means my horses, fishing, walking my dog and playing with my kids.
With this in mind my complete shoe collection is as follows:
Formal: 1 pair of black leather plain Oxfords from Church of England. Current pair 10 years old.
Smart Casual: 1 pair of the same shoes in dark brown leather. Current pair 8 years old.
Casual: 1 pair of Camper brown leather basketball style shoes to wear with jeans.
Sports: 2 pairs of white TopOne FeiYue sneakers (1 for indoor and 1 for outdoor). These do me for anything and everything from running, tennis, spring/summer/autumn hiking outdoors, to the gym, fencing, badminton and table tennis indoors. I rotate them so when the outdoor pair are trashed I swap them with my indoor ones and buy a new pair. This means a new pair roughly every 9 months at about USD15 a pair.
RIding and general field wear: 1 pair of Strathcona Boots from the Alberta Boot Company of Canada (as worn by the RCMP). A recent acquisition to replace a damaged pair of riding boots I’d had since I was 18. I fully expect to be able to hand these cracking boots down to my son in 40 years time!
Winter walking and stable work: 1 pair of lace up paddock boots from the Regent Shoe Company in England. Again a lifetime buy.
Fishing, snow, wet fields and mud, walking the dog: 1 pair of rubber Wellington boots of indeterminate age.
Experimental: Vibram FiveFingers KSOs for just about any time I’d prefer to be bare footed but don’t want to risk getting cuts or threadworms burrowing into my feet.
Taking out the trash/garden: 1 pair of flipflops by the back door.

That’s my lot. It definitely helps to enjoy polishing and caring for your shoes (a valuable legacy of a childhood in an English boarding school and a career in the army) as this will ensure that they last almost indefinitely with the odd heal and sole repair.

Art of Manliness is still the best blog on the Web. Nice one Brett.

84 Phocion Timon March 4, 2011 at 12:24 pm

The shoes in the last picture are ugly as a mud fence:

1) “Dress boots” look effiminate, and
2) the pointy toes are even more effiminate.

Has not anyone ever noticed our feet are not pointed? They are, generally, rounded. Pointy-toed shoes restrict the natural movement of the bones and muscles in our feet and are uncomfortable. Back when I put in my time in the saddle – I live in West Texas also – I wore the pointy-toed cowboy boots only while horseback. When I was engaged in any other activity I wore wide work boots. I caught a lot of flack over that habit but I can walk/run for several miles today while most of my friends can’t walk to the mailbox without discomfort due to their misshapened feet caused by years of wearing tight pointy-toed footwear.

Today, at 60 years old, I have gone to the “minimalist” side of footwear. (Google “barefoot running” or “minimalist running.” I pronate badly when running in modern high-tech shoes. One does not pronate when the feet are allowed to operate as evolution intended.) I am no longer involved in the cow business, having moved to oil and gas, but I still wear wide boots while in the field. (I have to order the boots online; brick-and-mortar stores carry only medium-width footwear.) I do not work in an office, and I don’t socialize, so dress shoes are not an issue. At home I am barefooted and when I go, for instance, to the grocery store, I am shod in the cheapest flip-flops I can find.

Apropos: the first thing I did when I bought my current boots was to take them to a boot repair shop and had them remove the heels and arch supports so the soles are flat fore to aft (and re-soled with Vibram’s 6mm “Cherry” material). Our feet evolved over two million years without raised heels or arch support and due to wearing the modified wide boots, my feet never give me any problem, even after several days of constant use. In fact, having gone this “minimalist” route for two years, heeled footwear hurt my feet after only a couple of hours and make my calf muscles tired.

85 Tom March 4, 2011 at 3:42 pm

I hate to nitpick an otherwise great article, but, I always thought Andy Dufresne stole the shoes of the Warden because he knew shoes were important to the overall look of a man. Anyways, great article and I look forward to the next one by Mr. Centeno.

86 Brett McKay March 4, 2011 at 4:25 pm

@Tom-

Andy takes the warden’s shoes and wears them back to his jail cell with his prison uniform. And the guards don’t notice. Later on when Red describes the escape, he says:

“In 1966, Andy Dufresne escaped from Shawshank prison. All they found of him was a muddy set of prison clothes, a bar of soap, and an old rock hammer, damn near worn down to the nub. I remember thinking it would take a man six hundred years to tunnel through the wall with it. Old Andy did it in less than twenty. Oh, Andy loved geology. I imagine it appealed to his meticulous nature. An ice age here, million years of mountain building there. Geology is the study of pressure and time. That’s all it takes really, pressure, and time. That, and a big goddamn poster. Like I said, in prison a man will do most anything to keep his mind occupied. Turns out Andy’s favorite hobby was totin’ his wall out into the exercise yard, a handful at a time. I guess after Tommy was killed, Andy decided he’d been here just about long enough. Andy did like he was told, buffed those shoes to a high mirror shine. The guards simply didn’t notice. Neither did I… I mean, seriously, how often do you really look at a mans shoes?”

87 Abby March 4, 2011 at 7:04 pm

I read this article with great interest and can only say THANK YOU! I will be forwarding it to every man I know. As for what piece of footwear you should write more about, I would love to see you write about why men should NOT wear sandals, flip flops, etc. I get that you don’t want to say something ugly, but anything that can be done to stop the madness of men wearing shoes that show their feet would be AWESOME!

As a woman, I’m not even a fan of most women showing their feet, but at least most women will try to make their feet presentable to the world. I love a big able-bodied working man. I do NOT love his feet, and cannot help but cringe when I see a man in public walking around with flip flops/sandals on, thinking it’s all good. I really hope I haven’t offended the flip flop crowd…

88 Andrew March 4, 2011 at 7:14 pm

I’d like to hear more about care. There was an article on shoeshining, but I don’t know how to make a good pair of shoes or boots last. Mink oil? washing off winter salt? Saddle soap? What materials should I not wear when it’s wet out?

89 Big Ed March 5, 2011 at 12:07 am

As long as we are talking about footwear, I’ve got 2, slightly unconventional, things to say:
1. Danner Mountain Lights! Unbelievable quality in a hiking boot. Still made in the USA. A little salty, but not horrendously high priced. The darn things last almost forever! (Boot Oil every week-do you hear me!) My first pair were re-soled after 4 years*. (VIBRAM-the first and only guys to get it right!) My second pair, which I bought when I sent the first pair to be resoled, are still nice enough to wear as dress.
I guarantee that you will not find a more comfortable pair of hiking boots. Note- do not buy these on line! Not sure what lasts they are using in Oregon, but sizes do not fit transplanted Westerners in the Back East.
*Includes all construction-related non-steel toe use and including regular dips in cow manure (I’m being polite here folks.).

2. Boy Scout moccasins – OK, this one is compliments of my 8-year-old. I got him the kit and got one for myself to practice on so I could help him out. A bit of a pain to assemble, they are the most practical property footwear I own. (These are not for public use!) I slip ‘em on first thing in the morning and wear ‘em outside and inside until I get dressed. The darn things are made in a foreign country (5 letters, starts with a C and ends with an a.) but still have the same quality I remember from ??? years ago.

90 Greg March 5, 2011 at 12:22 am

I run several quarries. Work boots are considered safety equipment so we provide them for our employees. As such we have tried several different brands and types looking for the best all around value. Caterpillar work boots came in dead last. They wore out even faster than the house brand boots we tried from Wal Mart. The only other boots we tried that were as bad as Caterpillar boots were Justin work boots.

If you are after good work boots, Georgia boot or Wolverine seem to provide the best value. They are far from being the cheapest, but their longevity makes up for their high initial cost. Typically a set of Georgia or Wolverine boots will last a year at the quarry, which is about the most demanding environment you can imaging. We tried 4 different style of the caterpillar boots and they lasted 28, 31, 31, and 37 days before they were worn to the point that they were considered unsafe and had to be replaced.

That said, my wife has a pair of caterpillar boots that she wears when she gardens or works in the yard, they have been around for 2 years now and still look like new, so if you are looking for work boots to walk around your mowed yard, the caterpillars may be a decent choice.

91 Dan March 5, 2011 at 7:50 pm

Clarks are actually a British company and have only been easily available in the US since the mid 90′s – In many cases they’re as easy (or easier) to find outside the US as Ecco.

92 MikeL March 6, 2011 at 8:38 am

I primarily wear 3 pairs of footwear:
1) Doc Martin 8-eye, black. My current pair is the 2nd pair I’ve owned in my life, the first pair lasting about 15 years, and these at the midway point with 8 years on them. I find them comfortable as well as fashionable, and pair them with jeans to casual dress pants like Dockers or my Scott eVest pants.

2) A pair of Durango cowboy boots, black. I rotate shoes every day to give them time to breathe, and the Durango boots are every bit as comfortable as the Docs, though I only pair them with jeans.

3) A pair of Vans. These are for around the house. I’m not into slippers.

I have other shoes for other purposes, but they don’t get worn much. For instance, a pair of black dress shoes I picked up at Sears 10 years ago. These are for my suits, which are only worn about 2-3 times a year, tops. I also have a pair of hunting boots, and a pair of running shoes that I keep telling myself I’m going to start using again when I have the time.

93 Ben March 7, 2011 at 7:32 am

If Colorado still made their steel-toed hiking/work boots I’d have to recommend them for the most comfortable and hard wearing all day work boots I’ve ever worn, and Windsor Smith for their stylish formal boots, but both of these companies recently stopped making their best boots – damn it.

More recently I’ve been wearing a pair of Steel Blue “Canberra’s”, which are a safety work boot with no metal, and just last week I bought my first pair of RM Williams dress boots, the Craftsman Yearling (black with “flat” heels).

The Canberra’s have been great for standing around all day (up to 3 and a half hours at a stretch) on a concrete floor or dirt ground, although they have this odd tendency to make my heels a bit sore when I’m sitting down for long periods (?!), and the leather is pretty damn thick and heavily stitched; I’ve dropped more than a few big chunks of stainless steel on my feet and left little more than a small scratch on the leather.

The Yearlings have been very comfortable as a walking around, sitting around boot, although the leather soles only have rubber on the heels so they get a little slippery on wet pavers and tiles; the girl in the store said I could have them with rubber under the entire sole but silly me didn’t take the option. They also have a shape that is very much like an oxford shoe below the ankle, except without the brogues or laces, so they’re good for casual or formal wear (I think so anyway, watch Layercake if you want examples). Ask me in a year though if they were worth the money.

94 Phil March 7, 2011 at 2:04 pm

The western boot is one of the best all around boots if you work outside in snake country, as under some stiff jeans or heavy duck it can provide a measure of bite deflection. Today’s westerns come with an enormous variety of soles compared to the old days, so you can get a pair for loafing, for riding, or for heavy work if you choose. There is one outstanding boot, however, that went unmentioned here and combines the features of several for an almost “universal” boot – the Wellington. You can use them for work, for loafing about, for shoveling shit out of the barn, and shined up there are some that can go to church. In the old days you used to see the gentlemen wear their cowboy boots even with a nice pair of slacks – it can still be done. Just don’t call them “ropers,” an unfortunate appellation used by many modern Texans for some reason that conjures images of a corny Roy Rogers.

95 Dan B March 7, 2011 at 4:40 pm

Recently appreciating (and sharing) The Art of Manliness blog and site.
It resonates like a timely social movement that’s a recapture of basic manly truth and a strong application of that truth for our time.

As far a shoes – I’ve always thought a man of action should have his feet covered, and appropriately so. I am taking note of the options outside my experience here, but would like to offer this;

A mature man looks silly in flip flops when not at the beach, in runners when not exercising, in work boots when not working and so on. Even boy scouts are prepared. How much more should a man know his purpose and be ready to fulfill it?

And a mature man always looks like a dumb-ass in crocs!

96 Covey March 7, 2011 at 11:57 pm

I loved this article. I have two favorite pairs of dress brogans that I wear all the time. Both are handmade to my feet. I’m very fortunate in one respect for working in a correctional facility because the inmates in the craftshops are absolutely amazing. Both pairs were made by the same inmate, and I watched the process from beginning to end to see the quality. I’ll probably own these shoes for the rest of my life, barring a couple of resoles over the time. I highly advise looking for a good cobbler. It makes a difference.

C. Barbee
Huntsville, Texas

97 Vintage Clark March 9, 2011 at 7:39 am

Come on man, you pick the saddle shoe but not the wingtip?

98 Anthony Davis March 9, 2011 at 3:04 pm

I would like to see an article about the appropriateness of shoes for each season.

99 Belligero March 10, 2011 at 2:17 pm

Caterpillar and Ecco are junk, Clark’s are also mostly junk as well. It’s well worth getting something that isn’t mass-produced as cheaply as possible.

100 Jeff March 10, 2011 at 3:43 pm

@ Peter,

The Motorcycle Boot Rules

I’ve sworn by motorcycle boots as my go to casual footwear choice for almost a decade. A conservative set of motorcycle boots actually looks very classic and all-American. Jeans, boots and a neat t-shirt is very “James Dean” if you will. My rule of thumb is, any occasion where you can wear blue jeans, you can pair those jeans with good motorcycle boots. You can also think of motorcycle boots as a more conservative alternative to cowboy boots. The look classic, manly, and authoritative. A guy in nice boots just exudes male confidence. (The extra ½ inch to inch of height it subtly adds doesn’t hurt either.)

First, avoid crazy “look at me, I’m a biker” boots. A single strap (or harness) is fine, but avoid multiple straps, lots of buckles, or adolescent embroidered designs. (IE: a 6 inch embroidered full color screaming eagle logo) When worn with your jeans over the boots, they will quietly assert themselves. If you want to be even more subtle, opt for a rounded to over a square toe (often called the “conductor” or “engineer” boot).

Second, buy actual motorcycle boots. Other types purpose made boots, such as a good hiking boot will work ok. Fashion boots will no, period. Respectable boots from a purpose made boot maker are not only better quality, but made by a company that understands the actual requirements for the boot. A popular fashion designer’s attempt at a motorcycle boot will only cover what they are generally supposed to look like. They will not last or perform as well.

A good set of motorcycle boots covers a few bases. It will be made of a good sturdy material almost certainly leather, and cover the ankle and part of the calf. This provides ankle supports, and more importantly, is meant to protect your legs from hot exhaust pipes (thus the leather). It will have a elevated heel. The heel is meant to catch and ensure that your feet don’t slip off the foot pegs. Finally, a good set of motorcycle boots will have a sturdy sole made of oil resistant rubber. This is what fashion designers miss often. Mounting or parking a motorcycle is a time when you want firm, non slip footing which wood soled fashion boots can’t deliver. The rubber is oil resistant because motorcycles leak oil (especially a certain well known American icon). You don’t want that oil to corrode and shorten the life of your boot sole.

Allow me to suggest one of my personal favorites. Frye boots has a reputable American leather goods and boot maker for about 150 years now. I’ve been a fan of their Harness Boot for riding and casual fashion for about 10 years. Remember these look much more subtle once your jeans are worn over them.

http://www.thefryecompany.com//Product-Men-Boots-Harness-87350BLK.aspx

http://www.thefryecompany.com//Product-Men-Boots-Work-87800GAU.aspx

Finally, a word about your ladies – It inevitable that we will try to get a young lady on back of our motorcycles. Its romantic, feels dangerous, obliterates the “touch barrier” and gives you the look of a confident type, while giving her the feeling of putting her safety in your capable hands. Long story short, women eat this up.

BE A GENTLEMAN and ask her in advance if she is alright with taking the motorcycle to your location.
Be sure gently suggest appropriate wear for her as well, (jeans being a good option here, depending on the make of your bike). Your date will not be pleased with you showing up on a motorcycle you expect her to get on, not realizing that she is 100% against being on one. She will not be a happy date walking around all night with an exhaust pipe burn on her ankle either.

Regards,
Jeff

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