Bringing Back the Hat

by Brett & Kate McKay on March 1, 2008 · 292 comments

in Accessories, Dress & Grooming


Up until the 1950s, men were rarely seen out and about without a hat sitting upon their head. Since that time, the wearing of hats has seen a precipitous decline. No one is precisely sure why. Some say the downfall of hats occurred when JFK did not wear a hat to his inauguration, thus forever branding them as uncool. This is an urban myth, however, as Kennedy did indeed don a hat that day. Another theory posits that the shrinking size of cars made wearing a hat while driving prohibitively difficult. Most likely, the demise of hats can simply be traced to changing styles and the ongoing trend towards a more casual look.

Hats are due for a full resurgence. They are both functional and stylish. They can cover a bad hair day, keep your head warm, and shade your eyes from the sun. They can also be worn to cover a receding hairline, which interestingly enough is why Frank Sinatra, an iconic hat wearer, started wearing one in the first place. They give you a touch of class and sophistication, impart personality, and add an interesting and unique accent to your outfits. And hats are a sure-fire way to boost your confidence. A cool hat can quickly become your signature piece and give you extra swagger.

Of course men today still wear hats, but they are most often confined to ratty baseball caps, hippie beanie caps, or the thankfully almost extinct trucker hat. There is nothing wrong with these kinds of headpieces per se, but there are other hat options out there. So mix up your lids with these various options:

The Flat Cap

Photo by Menno Ophelia

The flat cap has a rounded shape, a small brim, and a high back. Long associated with working class men in the UK, the flat cap can be a stylish way to add interest to a casual outfit. They can give your tired jeans and t-shirt look some unique style. Choose the more masculine flat cap over the similar, but rounder and puffier newsboy cap. The latter has been almost entirely co-opted by the ladies.

The Fedora


Fedoras were once considered de rigueur for men going out in public and a necessary accessory to formal and business attire. While once mainstream, a man in a fedora is now seen as a trendsetter. Fedoras are soft, usually made of felt, creased lengthwise down the crown, and pinched on both sides. Obviously you cannot pair a fedora with jeans and a polo. They are only an appropriate accent for dressier outfits. But the payoff — loads of style, class, and confidence — make dressing up worth it. Fedoras will make you look manly and a bit mysterious. Worn by Prohibition-era gangsters, almost all of the movie stars of the 1940s, and Old Blue Eyes himself, donning a fedora puts you in touch with a truly luminous and manly heritage.

The Porkpie

Photo from The French Connection

Named for its resemblance to an actual pork pie, this hat is similar to a fedora but with a flat top instead of a pinched crown. The brim is also shorter and turned up. The hat is often associated with the jazz, blues, and ska culture, but was also worn by the likes of Robert Oppenheimer, father of the atom bomb.

The Homburg

Photo from The Godfather

The Homburg is another hat similar to the fedora. The Homburg’s brim lacks the fedora’s pinches, and is turned up all the way around. The hat is accented with a hatband into which a feather may be stuck. Less casual than a top hat, and dressier than a fedora, the Homburg was the go-to lid for politicians and diplomats in the 20th century. Favored by the Godfather and resurrected by the likes of Snoop Dogg and Tupac, the Homburg now carries a distinctly gangster flavor.
The Bowler/Derby

Photo by Lainey’s Repertorie

Bowlers are hard, made of felt, and have very short brims. While considered a British icon, the bowler was also part of the urban culture of America in the 19th century. For example, one of the gangs that roamed the mean streets of New York City around the time were the Plug Uglies. The Uglies were never without their bowler hats, which they wore both as their signature piece and to protect their heads during their many scuffles with rival gangs.

Wearing a Hat


Cock your hat–angles are attitudes. ~Frank Sinatra

Hats can give you a feeling of effortless cool and manly confidence. Few people loved hats more, or wore them better than Frank Sinatra. He was constantly playing with the idea of angling and tilting his hat to convey different attitudes. Here’s how Frank wore his hat to reflect his mood:

  • Wear your hat pushed back to seem more open and accessible
  • Tilt your hat over your eyes to seem mysterious and intimidating
  • Tilt your hat up 1 inch from completely straight to project an all-business attitude

Hat Etiquette

In adopting the hat as your signature piece, you must also accept the responsibility of hat etiquette. Often ignored, hat etiquette will show that your uniqueness extends not only to you choice of headwear, but to your manners as well.

  • Promptly remove your hat upon entering an elevator, restaurant, or someone’s home. Never wear your hat during a meal.
  • Touch the brim of your hat lightly when greeting a friend.
  • Raise the hat by the crown when meeting a female friend in public.
  • Remove your hat during the national anthem and place it over your heart.

What’s your favorite style of hat? Do you have a particular favorite hat that you’ve worn for years?

{ 288 comments… read them below or add one }

201 King Kevin October 27, 2012 at 6:36 am

Picking a hat is most important. Don’t go for a specific style. Find one that fits your personality and face shape. Best way to decide if it fits you or not is to look in the mirror and decide if you see YOU, or you with a hat. Some people try to pull of these hats and it makes it look like the hat is wearing THEM.

It’s just advice.

202 Jared M October 27, 2012 at 8:04 am

I hunt almost every season, during small and upland game hunts I have my fedora on. It takes me back to hunting with Grampa he always had his cowboy hat on. The rest of the time its a old beat up Cabelas ball cap.

203 Anonymous October 27, 2012 at 4:28 pm

Top hat?

204 Emir November 4, 2012 at 9:51 am

Hey, you seem to have forgotten Top Hats, the most iconic hat used by Americans. Even used by the Man himself, Abe Lincoln!

205 Tony Viele November 15, 2012 at 2:13 pm

Worthy article.I love my hats,mostly fedora’s.Note my e mail name.Thought the comment on bringing back the codpiece was interesting.Wouldn’t work well with my kilt.Tony

206 Big Mike November 19, 2012 at 4:27 pm

Making a tricorne hat. Inspired by AC3.
Thanks for the info. Suggest you add: Never tip your hat to a bloke, particularly not an older one.

207 Mark November 22, 2012 at 7:15 am

Aren’t you supposed to take the hat or cap off when you enter a public building- school, courthouse, etc.? People do not do that anymore (amongst other things).

208 Mr. Jeff Aker November 22, 2012 at 6:46 pm

As someone who owns and on occasion wears a top hat. It’s a pain in the ass to put on a hat for formal events. Take it off upon entering and along with my gloves worry that some no class havin sketchy lurker walked with them. While I danced with my wife. So I now leave my top hat at home.

209 Jurgen De Cleen November 28, 2012 at 2:01 pm

It must be already ten years ago since I bought my first had (I was about 23 years old then). Now I wear a hat all the time, it became my trade mark. I think I have about 20 hats by now, mostly fedora and homburg style. For the summertime I have a couple of so-called Panama hats. I can’t imagine going out the door without a hat on my head…

210 Tyler December 7, 2012 at 3:46 pm

I haven’t really been a “hat guy,” but lately, I’ve been wearing a Russian-style fur hat I got as a gift, since it’s getting cold in Michigan. I’d like to start wearing more, but I don’t know what I should get for a first hat, or where to start looking for one.

By the way, there is a wrong way to wear a hat — just look at

211 Angelo December 7, 2012 at 7:18 pm

Am a hat guy too.
Am glad you said ” crappy baseball cap.”
It seems like people wear them everywhere!
I thought you suppose to wear them to support your team,AT THE GAME.
A friend of mine tried to wear a black baseball cap with a tux. Anyway-hats off to you!

212 Elliot Cherbu Steroids December 8, 2012 at 5:38 am

I hunt almost every season, during small and upland game hunts I have my fedora on. It takes me back to hunting with Grampa he always had his cowboy hat on. The rest of the time its a old beat up Cabelas ball cap.

213 Christopher December 16, 2012 at 2:59 pm

I used to don ratty baseball or a good beanie on “hat days”. Because of this article and the resurgence I’ve seen just in my town, I’ve purchased my first two flat caps and wear them with pride! Great article and better caps!

214 Curtis December 16, 2012 at 8:43 pm

I’m all about the resurgence of hats, and resurgence of a lot of things.. but let’s don’t forget to take them off indoors, including baseball caps! It’s not nostalgic nor fashionable if you can’t do it with the class of our hat-wearing forefathers.

215 JT December 20, 2012 at 10:56 am

I always wear a hat , but more of a Cowboy style hat. I noticed they weren’t mentioned in this article ?
I hate baseball caps , I have several that were given to me and don’t wear them. I prefer a good cowboy style hat with a leather chin strap because the wind out here will blow most hats off. :)

216 Reid December 28, 2012 at 9:24 am

So I have been greatly inspired to bring back the hat and I have been working on it for some time now. I follow all hat etiquette except for the part on removing my hat when I enter homes, meals, etc. I would except I get this horrendous hat hair. Any way to avoid this?

217 Luis December 29, 2012 at 11:43 pm

What about a beret? Not the military variation, but the one used in France or Spain, or by Basque shepherders. Classy and cultured look.

218 Jer January 6, 2013 at 1:02 am

I bought a wool flat cap a year-and-a-half ago and have been wearing it quite a bit. Sometimes I want to wear a hat and don’t want to dress like an adolescent. By the way, is there any headwear more heinous than the baseball cap with a perfectly flat brim (with or without various MLB and manufacturer stickers still affixed)?

219 Harvey January 23, 2013 at 10:57 pm

In Texas, the cowboy hat is still the hat to wear. Worn low, just above eye-level, is the douche-bag trend these days, though I hope cocked makes a comeback a la Roy Rogers and John Wayne. Always remove your hat inside a home, church or workplace, and remember your seasons: dark felt hat after Labor Day, light (straw) hat after Easter.

220 magicoddeffect January 25, 2013 at 4:25 pm

I’m 19. Myself and three of my friends wear hats nearly every time we go out. I’ve got quite a few, and only one is a standard ball cap. And most of these very unique hats have come from Goodwill stores.
Hopefully my generation realizes that proper hats, in the right shades, are excellent. Fashion is such a silly thing.

221 Taz January 26, 2013 at 1:51 am

What about the Aussie Akubra?

I wear one of these day in day out as do all my farming mates. They also have the added bonus of lasting forever.

222 Randy January 27, 2013 at 6:15 pm

I favor the comment someone made one time at The Fedora Lounge: something like, “When I attend a baseball game I don’t dress like a baseball player, I dress like a baseball fan.” So, whe I go to the ball game I dress like a fan from the 1930′s.

223 Clint January 30, 2013 at 10:28 pm

I’ve been looking for a semi-formal hat for a while, but local stores have a very limited selection… any suggestions for online stores or shops near southern Indiana?

224 Jesse February 2, 2013 at 1:10 am

Regarding the top hat, that’s seen exclusively with formalwear/ evening attire, if at all nowadays. So I can see why they’ve omitted that one from the article.

As for the hats-off rule, I always remove mine whenever I enter any building. Hats are there to serve a purpose; I’ve no need for protection from rain, snow, or sun indoors. It just looks silly and out of place indoors at all, not just in an elevator or home.

225 Timothy R February 8, 2013 at 2:42 am

I prefer a western style. I refuse to call it a cowboy hat due in part that the hats of the old west were many and not all “Cowboy Hats” were worn by Wranglers, Ranchers, or Livestock Men. Some were worn by Career Gamblers, Bankers, Teamsters, Wells Fargo Men, Railroaders and the like. So for me it is the Resistol Chute 5 style in Black with a Custom leather band. In real day to day life I am a Railroader by trade how manly is that for occupation. No pun intended we now share our ranks with the ladies…

However when not working I consider myself the Gambler, not the poker playing kind just a Gambler figure we all kind of gamblers since we roll the dice everytime you get behind the wheel of our vehicles and share the highway with other gamblers… Lifes a Gamble and if I lose I want to be in my best hat….

P.S. @ Work I still occassionally break out my trusty ol’ Pin Stripe special when in the mood. Bringing back old flair to new things is my passion….

226 Anonymous February 9, 2013 at 2:31 pm

You forgot my three favourite types of hat: the beaver and silk toppers and the boater.

These days the two top hats are only ever worn with morning and evening suits and so are worn with white tie. With morning dress people normally wear beavers or bowlers, although it’s rather open to personal tastes; with evening dress, an early type of black tie, it’s always a beaver or silk topper and with white tie it has to be a silk topper.

As for the boater it’s just a massively stylish, to state my own views, semi-formal cool summer straw hat that resembles a pork pie.

227 Charles Barax February 15, 2013 at 6:58 am

I didn’t read all of the comments but we Orthodox Jews may be the last Americans that continue to wear fedoras on a regular basis. Like any sub-culture, the details can e very telling. Baltimre. Brooklyn, Lakewood New Jersey ( to name just a few) have their own subtleties of tilt, crown, brim etc. Kudos on a great article.

228 Dee February 20, 2013 at 8:13 pm

‘Hats maketh the Man’. You can wear a hat with any occasion and with any outfit; be brave! And don’t feel your too old to wear certain hats; if you like it,your never too old.
I have every type of hat and adore them (at least 45!)! And probably will till I die!

229 Dave Thacker February 24, 2013 at 7:32 pm

I have a number of hats and enjoy wearing them. There is something about being in public in a hat. I notice people you interact with look at you more directly when communicating. Hats are cool. Nothing worse than a topless man. Love the article.

230 Christopher February 24, 2013 at 7:35 pm

Some here have referred to it as a top hat, but Abraham Lincoln more accurately donned a stovepipe hat. Our 16th president’s hat was beaver pelt, and if you have a chance to view one of his originals, you can view two worn spots on the top as a result of Abe’s hat-tipping the ladies.

231 Shea March 4, 2013 at 10:09 pm

Personally I wear an Oilcloth Aussie, bought as part of a costume a few years ago and never managed to put it down. It’s my trademark now. People recognize the hat, whether its in a store, on the street or driving down the road. It’s a part of me now. Just this past evening, leaving a restaurant an older lady stopped me and my companion to comment that I wore my hat well and how right it looked.
That, is the kind of hat you should look for, whatever type that may be.

232 Flynn March 16, 2013 at 5:22 pm

I prefer cowboy hats. Great sun and rain protection. I have a black felt one and a white straw

233 matt JSL tan March 20, 2013 at 12:28 pm

Cheers, enjoy your site. I used to wear a flatcap (yes to hide my messy hair) when I was a musician. I remember how many elder men wished me as I walked past them when I was traveling across Canada. I was very young then, but it certainly attracted a lot of respect from the older classier gents. Today I am part of that older gent, and I just picked up a hat which I , through your site , now know it ‘s a homburg. Now, I know , at last, after many years what Procol Harem was singing about with the song of the same name. I used to think Homburg was just another city like Hamberg, lol. I suppose I am older now, and I should know better, huh? Happy Spring Equinox, and cheers from Canada.

234 Chad March 24, 2013 at 8:57 pm

A rather interesting website, I applaud those who are making an effort to bring back proper male manners. As far as the hat goes, I have been wearing fedora’s and the cattleman’s hat since was in my teens. I grew up in Kansas and Texas. There is a sense of dignity in wearing a hat. In formal occasions I wear the Fedora, felt in winter and a straw version in summer. The western hat, I wear in both casual and work. I like clean crisp lines. My jeans will be pressed as well with a crease as It dresses them up. I agree with the hat protocol but would like to add to it, noting that a man should remove his hat when he meets or is introduced to a female. Manners are hugely important, and are mostly lost. You simply stand out now a days just by employing common courtesy and manners. Are table manners covered here? From what I have noticed many do not know how to eat at the table, might be a nice article for this site.

235 Thom March 27, 2013 at 6:20 pm

Finally, the hat is coming back. My father was never without a fedora even when it was not “in”. I have been wearing them for years and am pleased to see them reappear. It is great to find them in the stores again.

236 Dude April 1, 2013 at 11:18 pm

More on hat etiquette please. I was raised that men should ALWAYS remove hats when indoors, I’ve seen plenty of fedoras being worn in bars, shops… just seems wrong. Might be a good subject for an article.

237 Brian Clark April 2, 2013 at 12:16 pm

Great article! Remember to find a hat that’s of an appropriate size. IMO, nothing looks more ridiculous than a guy who wears a hat that’s too small for his head…

238 Mike April 8, 2013 at 4:06 pm

Clint, you might try Henry the Hatter. Great store here in Detroit. They have an online store as well. Great old-fashioned place; stop in if you ever get an opportunity.

239 ayush banerjee April 11, 2013 at 4:51 am

awesome hats indeed.

240 Palifox April 13, 2013 at 4:34 pm

I started wearing hats when the inevitable bald spot appeared. I walk to work and though temperatures here rarely go below -5 centigrade in mid winter a flat cap or almost anything is great. I’ve attended many car club concourses and a baseball cap does not cut it when you’re showing a classic Mercedes. So out comes the beige cotton Fedora or a grey felt hat with broad brim and pork pie style crown, plaited leather band. Complimented by two younger ladies when I first got it, BTW

My mother used to say “The broader the brim the smaller the sheep station.” (ranch).

The Homburg was considered more formal than the Fedora but appears to have derived from hunter’s hats . There are details over at the “Gentleman’s Gazette” site.

A small business in Donegal Town, Ireland makes wool flat caps to order or chose from their range, Google them

241 Nate May 13, 2013 at 3:40 pm

The cowboy hat wasn’t mentioned – aside from the urban enclaves who can’t believe they actually ARE in the west, if you’re west of the Mississippi, a cowboy hat is appropriate in most places.

And why not wear them east of the Mississippi too?

242 Uterus Owner June 17, 2013 at 11:24 am

I was only on here to figure out how to sharpen a pocket knife, but what the hell.
Dudes, classic dress hats like fedoras are ONLY attractive if you wear a dressy outfit to match. Please, don’t wear them with a t-shirt and jeans/shorts. Women actively avoid guys who are guilty of this due to the high probability that they also own a katana and enjoy My Little Pony way more than necessary.

243 Tone July 5, 2013 at 2:46 pm

I’ve been wearing a fedora for about 3 years now and i love it. Felts in the winter, panama in the summer and canvas for the spring and fall.

244 Wasim July 25, 2013 at 10:45 am

Nowadays I see a lot of these hats that look similar to fedoras except their brims are more narrow and they are worn with casual clothes.

What are these called and are they recommended for the manly man?

245 dan July 26, 2013 at 12:49 pm

I must add the ubiquitous knit- wool touque or balaclava (brimmed,of course)
…derigueur in northern climes although
(I preferred mine aboard my ice-breaker to a ball-cap) and my sheepskin Mushers (mad -bomber)cap.

246 Nicholas Welch July 29, 2013 at 1:07 am

A problem I’ve noticed with the “resurgence” of hats is the way it’s occurring. The modern usage of a hat is almost exclusively function. When hats are worn as a stylistic piece it is different from the norm. Traditionally hats were both form and function, with one taking precedence over the other depending upon the situation.

However, hats as stylistic pieces today are seen mostly being worn by older gentlemen who would have been present while hats were more common place, which does not carry the influence in modern times that it used too. The elderly are often not seen as the examples they once were.
The other is located on more fringe parts of the spectrum, which people often don’t want to be associated with. One such fringe element would be best qualified as the “hipster” trend and pretentious individuals who pride themselves as “artists” or something similar. Those who feel that it makes them classier, like the stereotypical “douche-bag with a guitar,” or sets them apart are detrimental to the resurgence.
Many of these fringes associated with the wearing of more classical/stylistic hats carries a negative connotation and discourages the younger generation of upcoming men (myself included, and being a university student I see much of this interaction around me) from embracing the hat, in fear of being compared to “basement-dwellers” or those who are pretentious and full of themselves.
Another issue is that the knowledge of hats has faded. The fringe who champions the hat are often proponents of what they assume is the fedora, which is actually a trilby, a type of narrow brimmed hat. These are the flamboyant type with wild patterns and odd materials you see on racks and shelves in department and clothing stores. The hat is misunderstood. The lack of knowledge is detrimental. A hat like the trilby, and sometimes a true fedora, is not worn properly. Dressier hats are worn casually by those the majority see as weird, and not without reason. A tie isn’t worn with a t-shirt and jeans, why should a dress hat. The idea of a dress hat lingers from our grandfathers, but it isn’t embraced. The minority who do often do it wrong. Since hats dropped off they haven’t kept pace with style over the past few decades. What is casual now was not casual back in the 50′s, when hats were more prevalent and worn in both casual and formal settings.
While I think a resurgence of hats would be a relatively positive thing, the hat, in modern view, has been tainted and has some catching up to do.

247 DAVid August 14, 2013 at 10:49 pm

On the coronation of Queen Elizabeth II, the BBC did not broadcast the event on wireless, because they were concerned that it would be listened to by men in Australia drinking in public houses wearing their hats. Ever since then I’ve worn my hat in pubs, though these days, with CCTV wanting a clear view of us all, I’m often advised to remove it. With the worlds highest incidence of skin cancer we here should wear hats all of the time. I for one am trying to resurge it. I can recommend the Akubra Stylemaster. Great article. Thanks.

248 Dave August 17, 2013 at 11:28 am

Bravo! Great article! I’ve always liked hats, so when I joined the military, their insistence on soldiers wearing “covers” came naturally to me. More on that in a moment. I’ve continued to wear hats in the manner prescribed in the military because of my elevated risk of skin cancer, and as I get older, and my hairline recedes, I’ve learned how valuable hair is to one’s comfort. Never mind style, a bald head gets hot in the summer, and cold in the winter. A hat does a very good job as a hair substitute. Long ago I was taught, and experienced myself, “If your feet are cold, put on a hat.” Sound crazy? It’s true! Hats keep me cooler in the summer, and warmer in the winter.

Funny thing about what people call “military etiquette.” Many today consider it to be silly. In fact, all the military has done is to codify, and teach, good manners. And so it is with the hat. Outdoors, always wear a hat. Always remove the hat when you go indoors. There are exceptions: Remove the hat and place it over the heart for things like the Pledge of Allegiance, the National Anthem, etc. It’s really the civilian version of a salute. Even in the military, hats are customarily worn indoors during formations. But if you stick to the hat-outdoors-and-uncovered-indoors rule, you can hardly go wrong.

There’s one other exception, fairly new. Those who are, or have served, in the military are authorized, as they wish, to remain covered, and render a proper hand salute, even when in civilian clothes. This would be in the case of the passing of the flag, the Pledge of Allegiance, or the National Anthem.

One final note: These rules about hats being worn or not, apply to ALL hats, INCLUDING baseball caps and “cowboy hats.”

249 Talon August 25, 2013 at 1:54 am

Greek Fisherman Cap.

250 Mike August 25, 2013 at 8:43 pm

Trying to find a new hat to wear and I see a ton of comments that wouldn’t be out of place in some coffee shop filled with 90 year old men bemoaning how horrible younger generations are. Men should work on their manners via wearing hats…ok…well someday when I meet a lady maybe I’ll put enough effort into worrying about gentlemanly hat specific behavior. There’s something to be said for “classic” behavior but don’t equate it with superior behavior.

251 Evan August 30, 2013 at 5:27 am

What about the good old classic baseball cap?

252 Zachary McAllian September 6, 2013 at 3:42 am

I wear a Belfry Topper, cocked ever so slightly forward. I think I may switch to something shorter, with a wider brim, however.

253 Kyle September 23, 2013 at 1:23 am

What kind of hat does Indiana Jones wear?

254 Chris September 23, 2013 at 2:34 pm

I’ve been wearing a black alpine hat.

255 GrouchoMarxist September 29, 2013 at 8:17 pm

Not mentioned is, for summer wear, the old Boater. Those straw hats that were ubiquitous back in the early Twentieth Century. I have a couple of these. I am sure they used to be an inexpensive item bought new each year. The ones I have cost about $80.00.

256 Tom Abel October 5, 2013 at 9:12 pm

I have a question rather than a comment. I own and wear a numbe rof different Fedora hats but do not have anywhere in my city to have them blocked or cleaned, Any suggestions from anybody?

Thank you!

257 Rick October 15, 2013 at 12:52 pm

@Nicholas Welch
Well said! Reflects my feelings exactly.

258 Matt October 17, 2013 at 8:49 pm

Geat article. Man, love this site!

259 John October 23, 2013 at 7:47 am

I’ve been rockin hats for years! Only recently have they been easier to find! I love pork pies or stingy brims and fedoras. I have ball caps, cowby hats, fedoras, pork pies and “outbacks” ! I’m glad they’re easier to find but bummed everyone is flitching my style!!!!

260 William October 30, 2013 at 5:01 pm

I enjoy 3 different color fedora’s but sometime have a difficult time finding a place for to rest my hat when I’m at a restaurant, club or other similar places. There needs to be a return of the hat rack.

261 G Caldwell October 31, 2013 at 8:42 pm

I love a flat cap and wear one all year round. I’ve got about 6 or 7 now, for different occasions, but the best by far is my patchwork cap from Hanna Hats in Donegal, Ireland. I found out about them through a friend, and each one is unique. The mix of colours, patterns and textures means it matches pretty much any outfit.

262 Donald November 3, 2013 at 8:58 pm

I wear Stetson “cowboy” hats, panama and 5X Beaver, but I keep a crushable
hat in the truck.

263 Louie November 7, 2013 at 11:37 am

This is my hat of choice. I wouldn’t pair it with a suit and tie, but I’ve spent enough time wandering in deserts that it fits me.×400/9df78eab33525d08d6e5fb8d27136e95/i/m/image_64484.jpg

264 Scott Dunn November 15, 2013 at 11:43 pm

I actually had a question about when to add a hat with a suit. Below is the suit I’ll be wearing to a company Christmas party. It’s my first suit and off the rack but I plan to go custom in the future.

Hat too much?

265 Hecklectic November 16, 2013 at 8:28 am

I’m absolutely SICK of ball caps, forward or backwards or more appropriately sideways! Most of them are billboards. Idiocy! My Dad wore a fedora in the cool months and a panama in the warm months. I’d love to see some REAL hats being worn again!

266 Jon November 17, 2013 at 4:27 am

For the sake of interest, I’ve been reading through the comments on this years-old hat post.

I respect people’s passions and preferences, and I think common courtesy and common sense are fairly obvious with where to wear a hat and where not to.

However, a baseball cap is a 21st-Century hat. The casualness but everyday-wear of baseball caps is likely what these fedora etc. hats were to the early 20th century, give or take.

The across-the-board knocking of baseball caps is ridiculous. No, they don’t look good with a suit. But if I see you wearing a hat from a mid-1900′s movie, meandering around on a Saturday through Anytown, USA, I’m going to think you look a bit silly and probably quite arrogant. Common sense goes both ways. Class is more than just clothes too.

If you wear a fedora et al. type of fancy hat, you are likely peacocking and trying to make a fashion statement you want others to see, and probably are at least a little aggressive about how everyone should adhere to the world how you see it.

Otherwise, this is a hobby, good for you fellas, you do look nice, I suppose, but remember others have every right to NOT look like you and that does not make them trashier or lazier than you.

Happy holidays to all!

267 ed November 22, 2013 at 2:59 am

I gotta say, most men under 70 can not pull off wearing a fedora or fancy hat of any kind. We’re in the post-JFK era, people. Old fashioned hats are not coming back. You may as well put a giant ostrich feather in your cap and tie an onion to your belt. Dressing like a man is not about plopping some 50-year old affectation on your head. Just wear clothes made for grown-ups that fit and are made well. Hats are not a shortcut to being a classy guy.

268 Bob November 22, 2013 at 11:17 am


You may be correct that the baseball cap is the common hat of the late 21st century. However, that does not mean that we are required to like it or to agree to abide with your notion that it is acceptable wear. If we wish to make the effort to find a hat that does not look like trash and to wear it, I think that it perfectly acceptable for us to do so, and to raise the bar for those that do not choose to expend the effort towards looking classy (instead of trashy).

Granted, if you see someone wandering around with a fedora on and wearing jeans and a ragged t-shirt, they probably are a bit of a twit, but wearing a nice hat that goes with a nice suit/ jacket looks infinitely better than jeans and a ball cap.


269 Xak November 29, 2013 at 6:47 pm

Scott Dunn, a hat wouldn’t be too much, so long as it matches (gray), but honestly if you want to look classy, I’d see if you can get the suit tailored. Bespoke clothing is beyond the reach of, well…most folks. Me, certainly. But you can usually get an off-the-rack suit tailored for not too much (about what you’d spend on a nice hat) and the difference is amazing.

270 William December 3, 2013 at 1:10 pm

Who can forget the Heisenberg in Breaking Bad? Once he started wearing his Porkpie it was like the crown on the indisputable king.

271 Walt Grant December 6, 2013 at 11:11 am

I’ve been wearing an homburg for a while now. I got it at the local hat store. The man working there told me that he couldnt sell the homburgs at all and gave me a 90% discount!!! I am still having trouble with the whole etiquitte thing though.. Is it allowed to wear your hat in the train and such?

272 Putt December 12, 2013 at 10:13 pm

I’ll confess that I am a hat junkie. Panamas, bowlers, fedoras, newsboys and berets all have a place on my hatrack, when not on my head. Obviously I applaud the hat as a mater of style, but also of practical necessity. These New England winters get cold.

273 Carlo December 16, 2013 at 3:55 pm

+1 for the Aussie Akubras. I’ve still got one I bought in 1970.

Their selection of “fedoras & dress hats” has something for just about anybody whose looking for something for casual to office-casual wear, or to wear with a trenchcoat.

For wear with the ol’ cashmere or overcoat, you might want something softer.

And if you’ve got a Chesterfield overcoat with a velvet collar, only a Homburg will do.

Excellent article!

274 D.E.G. January 5, 2014 at 7:43 pm

In conjunction with the many articles on dressing better and building an interchangeable wardrobe, I decided to upgrade my baseball cap. This is a little daunting, and takes ‘practice’ to get used to wearing a proper hat. However, I found it to be a very rewarding experience. I took my new hat with me to the chilly midwest over the holidays, and had no problems keeping my head (and ears!) warm while out and about in the freezing temperatures. I also received numerous compliments on how good my new hat suited me. My only suggestion to those wishing to upgrade their ball caps: Try on A LOT. I easily went through 10 hats before I found one that worked for me. But once you find it. . . you’ll know.

Thanks to Brett and Antonio for their sound advice on dressing properly for the day.

275 Jim January 23, 2014 at 6:19 pm

I like Tilley hats. I wear them when I work outdoors. They are good quality and have a lifetime, no questions asked return policy.

276 RMB February 4, 2014 at 8:43 am

I would love to be able to wear hats, but don’t like my hair to get messed up. Is there a hat friendly way to style your hair so you look good both inside and outside?

277 Barry February 19, 2014 at 2:21 pm

I hate to be the one to say it, but most of the hats in this article are completely out of style and would make any person today either look ridiculous or like they stepped out of a play. Bowler? Pork Pie? Seriously? Please do not wear these. The only one that has a chance of being wearable today is the fedora, and even that makes most people look like an Indiana Jones wannabe unless it is sheltering the wearer from cold, snow or rain. The flat cap gets a little cold weather use, but is really better worn for that purpose only and put away for other occasions. I wear hats frequently, but something practical for sun protection or in cold weather rather than as a fashion statement. If a certain formal look, style or fashion is what you are going for, you will be much better off not wearing a hat at all. Sorry, guys, that’s just good common sense. There are many great articles in this collection, but this one misses the mark as far as credible style advice. If you live in Texas or similar places, you can wear a cowboy hat in many cases, and baseball hats are often practical and acceptable casual wear, but if you are trying to sport a homburg, it will be shouting that you are trying too hard, and really have no clue what to wear, and that is the opposite of stylish.

278 Rob February 27, 2014 at 9:15 pm

I wear a hat every day. One with my postal uniform, a wool flat cap or fedora in winter, a straw Panama or boater in summer.

279 Jasmine February 28, 2014 at 5:59 pm

My grandfather wore homburgs and fedoras (think Clark Gable and Walt Disney combined) and he looked great. However some guys dont. Its about picking one that goes with your face shape and colouring. Experiment with a good clear mirror and some cheap hats in various styles say from ebay before buying the one for you. Roughly a small face looks wrong with a large wide hat like a sombrero and top hats with a long face accentuate it. A rakish angle with a panama or fedora looks good with any face shape especially slightly round as it contrasts and balances it out. I am a woman (1940s ish and Kate Bush) and I love my black fedora and white cossack fur hat and wear regularly. Classic shades like cream and black look better than red or striped say. Also measure round the widest part of your head and know in inches or cm and convert it to hat size online. Nothing worse than a “headache hat” or one that looks like your head lost weight! Also dont be scared to try womens hats as they have a better range. HandM in the Uk do fantastic manly womens trilbys and Fedoras.

280 james March 2, 2014 at 3:08 am

I never wear a hat to work it would ruin it. but only high days and holidays.I LOVE my fedoras.i have three of them.I do see my sons friends sometimes wear ” tea cosies” I don’t get them at all.What happens when it rains or is wet and windy horrible! I would love the fur felt hat to return…I think it is. because it is stylish and the general public or fashion world have come round to this……………finally!

281 Daibach March 4, 2014 at 11:44 am

I wear a Fedora when out walking the dog.I usually wear it with my black overcoat or fur collared top coat.
One is always greeted respectfully if you dress the part. If you want to blend in go with the flow and be one of the masses, or man up! Stand tall the ladies seem to love them. When at the races though you are not alone. Dave

282 Mr. Bab March 4, 2014 at 10:25 pm

I love my golf caps, especially Dallas sport teams that I can wear out of town. I do wear them with blazers, notably like Marc Cuban, to appear not too dressy. it is just my thing.
In regards to etiquette, I understand the history but if we were to following the history of everything is ridiculous and can be miserable. I trust your roof isn’t leaking when I enter your home and I’m not hiding a knife in my hair. I think it’s ridiculous, no?

283 Shawmutt March 5, 2014 at 9:41 am

I am partial to Tilley hats. I needed a hat for a boating tour, and happened to find a Tilley hemp hat that was everything I wanted. Then it just kind of stayed on my head all the time.

It’s functional, but it’s floppy and ugly. I wanted something nicer to wear and went to Tilley and got their Montana hat. It’s kind of a cross between cowboy and fedora, and much more interesting than a knit cap. It’s functional as well, with drop down ear covers tucked in the cap for the really cold days.

When spring came along I again went with Tilley, the Shantung Fedora.

I love my hats, and will be getting plenty more as time goes on!

284 Max Rowland March 7, 2014 at 12:07 am

As a Revolutionary and Civil War reenactor, I know a thing or two about hats. Being both tall and stocky, my preferred hat is either a tricorn(not great for general use) or my signature plantation owner’s hat. It’s black fur-felt with a very low, round bowler-esque crown, and a tremendously wide straight brim. Great for the miserable Long Island summers!

285 Ted Grodecki March 8, 2014 at 7:24 pm

I own a fedora, pork pie, and a bowler. I usually wear the bowler most often. I wear them all the time regardless of my wardrobe. I can be in jeans and be found wearing a bowler. I’m comfortable and really don’t care what others think.

286 David Windsor March 19, 2014 at 5:33 pm

One word


They make a number of great looking hats, some guaranteed for life not to wear out.

I own 3.

287 Nate March 24, 2014 at 11:40 am

I prefer to wear an ivy cap. My favorite is a knit, grey cap that goes very well with my cardigan of the same color. Unfortunately, I’ve misplaced it, and its been missing for over a month.

288 John Edward Gammell April 9, 2014 at 7:45 pm

Don’t let any of these fools, trolls, idiots, pretentious snobs, or other charlatans tell you that you *can’t* wear dress hats or you’ll “look ridiculous/stepped out of a play/have no clue what to wear properly/can’t pull it off/are under 70.

These morons are mostly mean-spirited and/or jealous idiots who think they can dictate what articles of clothing you can and can’t wear. Who cares if they aren’t as common as they once were. A great, well-fitted dress hat worn properly always looks good (although do try and avoid pairing it with a ratty t shirt and jeans). So if these imbeciles try to give you trouble, laugh at you, or otherwise belittle you for wearing a hat you personally enjoy, just smile and wave at the bullies, and know that they probably lead miserable conformist lives. They are welcome to think “hats are dead, we’re in the post JFK era, or PLEASE don’t wear any of these.” Yes, they are welcome to be wrong and be one of the grungy t- and jeans ballcap masses. They are not however welcome to try and decide what others CAN or CAN’T wear.

TLDR? One famous Latin phrase sums this all up fine: nil bastardum carborundum. Don’t let these b*******’s get you down.

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