6 Holiday Style Tips For Men

by Antonio on December 4, 2008 · 23 comments

in Dress & Grooming, Style

The holiday season has begun, and for the next month many of us have a full schedule. From work-related parties to the traditional get together with friends and family, you’ll need to dress appropriately as you mingle with the boss and trade stories with uncle Bob. With many of these events scheduled for the same day, you’re going to have to balance comfort, style, and versatility. And believe it or not, this is easier than you might think.

1. Layer – learn to overlap cotton and wool clothing appropriately
Whatever you are going to be doing, you want to be comfortable doing it. A big part of that is wearing clothing that doesn’t cause you to overheat, allows your skin to breathe, and protects you from the elements. Both cotton and wool are time tested fabrics that when layered appropriately can help you make it through the holidays without freezing or breaking a sweat.

Cotton, the world most popular fabric, is what you want to wear close your body. Cotton fibers are a cellulose based fiber whose natural properties allow it to pass both heat and moisture, thus making this clothing breathable and light feeling. Cotton briefs and undershirts are inexpensive and provide you exactly what you need; 100% cotton dress shirts are usually priced a bit higher than blends, but if you expect to sweat there is no substitute for its wicking properties. A bonus is that cotton is very durable and can be safely washed at home with regular detergent, although acidic stains (such as those caused by wine) should be treated immediately.

Wool (and other protein based fibers such as cashmere), on the other hand, does an excellent job of retaining heat; thus these natural fibers are an excellent choice for a jacket, sweater, or overcoat. Wool also has the unique property of being able to absorb moisture while not feeling wet; thus the melting snow on your shoulders will disappear quickly and not spread. Little things like wearing wool socks and ensuring your knit hat is made of wool or cashmere (vs. cotton) will help you stay much warmer without adding any bulk. However, treat wool like the premium fiber it is. Water weakens wool’s strength, and it can be misshaped if hung up on a hanger when wet (instead lay out on a flat surface). Finally, never expose wool to extreme heat such as an iron; if you need to work out wrinkles, use a steamer so you don’t damage the fibers.

An ideal cold weather holiday outfit would combine 100% cotton underwear and dress shirt with a pair of wool trousers coupled with a wool sweater and jacket protected by a wool overcoat. If you find yourself sweating, you can rest assured knowing the cotton will wick the moisture from your skin and your wool jacket will absorb it with no noticeable effects. And by layering, you can always adjust your own personal thermostat by un-layering (try to keep your jacket on….unless the party gets lively!).

2. Invest in an Overcoat
You iron your shirt, polish your shoes, and adjust your tie – only to ruin the entire presentation by tossing on a bright red ski coat or old leather motorcycle jacket. Does this sound familiar? When it comes to a professional looking coat, many of us look at this as a luxury. But in the winter, your outerwear is the first and last thing many people will see you wearing. If the event is outside, it’s the only thing they’ll see. Far from being a luxury, a good overcoat is must for any man living in a region that experiences cold weather.

Unlike shirts or even suits, most men need only one overcoat. As such, it’s worth spending the resources to ensure it looks great on you. Start with fit; a $200 overcoat that fits a man perfectly always looks better than a $2000 overcoat that’s two sizes too big. First ensure the shoulders fit well and have a style that compliments your build – this cannot be altered. Next, look at the sleeve length, and have them adjusted to cover your jacket and shirt cuffs but not your hands. Finally, have a skilled tailor tighten the jacket around the torso and have its length adjusted to your tastes. As for fabric, as long as it is made from wool you are good to go. More expensive overcoats utilize a wool & cashmere blend – the added benefit here is drape and softness (not heat retention).

An overcoat does not stand alone – ensure you supplement it with a wool or cashmere scarf & knit hat and insulated leather gloves. For reasons mentioned above, it’s worth spending a little more for quality accessories made from the proper materials that will do their intended job.

3. Wear a Jacket
Many holiday parties will not require a suit; however this doesn’t give us the freedom to show up in sweats. This holiday season consider wearing a sports jacket or blazer – match it with a pair of jeans and button down shirt for a casual yet professional appearance at your company’s afternoon Christmas party and then transition seamlessly to the evening’s get-together with friends downtown. There are a number of advantages sports jackets and blazers have over dress shirts alone:

  1. Jackets build up your shoulders; this makes you look taller, and broad shoulders create a more masculine appearance.
  2. A jacket and dress shirt fits within the business casual dress code – this means you can skip the tie.
  3. For those with larger midsections, a jacket helps hide extra weight.
  4. Interior pockets are a great place to keep phones, money, business cards, and beats stuffing your trouser pockets.
  5. When your date or significant other says she’s cold, you have an instant solution.
  6. It just looks cooler.

4. Avoid the Seasonal Tie & Socks
They appear every holiday season, and like good soldiers we accept them with a smile and wear them so our loved ones can see that we really do appreciate their thoughtfulness. Clip-on Christmas ties with Santa Claus and the bright red socks with Frosty the Snow Man: really, why do we do this to ourselves?

Here, more than anywhere, an ounce of prevention is worth a pound of cure. The best way to stop this from happening is to subtly suggest an alternative gift that is easy to find, light on the wallet, and supports a great cause. Two of my favorite small businesses that fit this description are BOGO Light (former U.S. Marine Mark Bent sells reusable solar powered flashlights – half the proceeds are used to deliver a BOGO light to African families who have no electricity) or Wurkin Stiffs (innovators Jonathan and Amie Boos sell their invention, magnetic collar stays, directly to the public – its an incredibly useful item for anyone with fussy collars).

5. Opt for Dark Trousers or Jeans
Snow turns to muddy slush, and you can bet you’re going to get some splashed on you. Leave the khaki’s at home and wear a pair of dark trousers or jeans that can take a piece of dropped cake or spilled glass of eggnog without you having to change outfits. This tip also works for dates and interviews; as men, the one time you forget to “shake” properly is when you are going to be stuck confronting your date with an embarrassing wet spot near your crotch.

6. Always carry a Handkerchief
A gentleman should always be ready to help a lady, child, or fellow man in need. Carrying a simple white cotton handkerchief in your back pocket is a habit that’s inexpensive, easy to pick-up, and allows you to come to the rescue in a potentially embarrassing moment. Oh, and the proper response when they thank you is to say “You’re welcome, and please keep it”.

Written by
Antonio Centeno
Quality Custom Clothing & Sound Style Advice
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{ 23 comments… read them below or add one }

1 Dave December 4, 2008 at 10:24 pm

Great tips, but it should be mentioned that the pockets of your jacket are not to be stuffed too full. This might ruin it, and also looks stupid as too many junk is visible from the outside.

2 Bob Iger December 5, 2008 at 6:08 am

Great style tips, Tony! I concur with Dave’s remark.

3 BRZ December 5, 2008 at 7:14 am

Just last week my wife and I went out on a nice date night and all I had to wear was my vintage cafe styled biker jacket or my heavy Columbia ski coat! Neither one looked good with my clothes but that was all I had. I’m hoping for one of these in gray from Stormy Kromer for Christmas:

4 Daryl December 5, 2008 at 8:32 am

All great tips but I would take care with putting that hanky in the back pocket. You may unwittingly send the wrong signals, which are perhaps most unmanly:

5 Jack December 5, 2008 at 10:43 am

Excellent entry filled with helpful tips.

I live in Southern California and I don’t have the pleasure of nice, cold winters. Even though its usually ugly, and hot, I’ve been wanting to get a nice coat to wear on those rare occasions that its cold enough to wear one.

Thanks Antonio!

6 JC December 5, 2008 at 2:47 pm

Point 3 (5) is worth the whole thing, but more attention should be paid to the humble pocket handkerchief. Always carry AT LEAST two. I have trained my hordes of friends and admirers to give them to me as gifts for my birthday and for Christmas – easy to remember, and easy to afford.

7 Joshua December 5, 2008 at 3:02 pm

Another amazingly useful post, which is what keeps me coming back to this site. To expand on Dave’s comments, and granted these are only my personal opinions, if you have a vest with pockets, put your phone in one of them (if it’s a small phone like mine is), and put your wallet and pen (you’re never caught without a proper pen, are you?) in your inner jacket pocket. That provides you with a decently even distribution of stuff. If you have a thick wallet, put it in the lower inner pocket of your jacket, if you have one.

Let me reiterate, this is just what I’ve found works. Maybe it’s the cut and tailoring of my jacket, maybe it’s my build, but it does work for me.

8 Oracle989 December 5, 2008 at 3:05 pm

Well compiled list, Tony. I’ll have to keep these in mind.

9 Shaun December 5, 2008 at 6:03 pm

Antonio, you’re a god among men. Thanks for another great article!

10 Jeff December 5, 2008 at 6:45 pm

re: Overcoats

A long overcoat is much more stylish than a short one.

Walking downtown in the Chicago Loop, I notice how a lower-calf-length coat looks much more adult than anything shorter.

Pea coats, ski jackets, just-below-the-knee coats…subtract 10 man-points for every inch above the ankle.

11 Tony December 6, 2008 at 5:23 pm

@Dave@Bob Iger – You’re absolutely right guys, all things in moderation.

@BRZ – That Stormy Kromer looks like a great jacket – just ensure you get the right fit. So many of us wear a large when we should be wearing a medium.

@Jack – Southern Cal is a hard place for an overcoat to find use. But all the more reason to visit the family in Boston for Christmas!

@JC – I debated talking more about the pocket square, but decided to leave it out. But you are right JC, pocket handkerchiefs are simple gifts that every man can use and too few men utilize. It separates a man in a suit from the crowd; it says I want to wear this outfit, I look good, and am not afraid to display some style. Just make sure to fold it right and coordinate it with the outfit!

@Joshua – Thanks Joshua for the details!

@Oracle989 – Thanks Oracle989!

@Shaun – Shaun, my wife read this and then sent me to the Kitchen to do dishes. Thanks!:)

@Jeff – I wouldn’t be so tough on shorter coats; they can look great on some body types and if cut correctly are a great alternative to a longer coat in the fall and spring. Also, if you do a lot of driving a long coat gets in the way. Legendary short coats like the Barbour and quilted coats are prized by many who can balance the look. But in general they are more difficult to pull off.

12 BRZ December 7, 2008 at 8:38 am

Don’t forget the excellent write up on rocking a pocket square here

I wore one last night to a work party and, paired with a vintage Dobbs fedora, I received several compliments.

13 Carlos December 7, 2008 at 2:20 pm

Everything was spot on until you mentioned the hankerchief… I have seen them in action… they are disgusting…

14 BRZ December 7, 2008 at 2:50 pm

Hey Carlos,
You’re supposed to wash them between uses : )

15 Matt Fox December 28, 2008 at 8:10 am

Amazing illustration.

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17 Dakota December 12, 2009 at 5:48 pm

Good article! One thing to remember though, is you don’t want cotton next to your skin if you’re going to be doing physical activities or outdoor activities! Cotton will absorb the moisture of your sweat and won’t let it go like wool or synthetic will, and you will freeze! As much as I hate the cheesy saying, when it comes to the outdoors, “cotton kills.”

18 Eli December 14, 2009 at 10:16 am


Always carry a Handkerchief *and* tissues. I never use my handkerchief for my nose or such things, as they have other uses. I use the Kleenex for my nose and to offer others. I keep one Handkerchief unused (to offer to the ladies), and one gets used occasionally by myself for various things.


Great article. Well said. I have a 3/4 length overcoat that I wear in the winter. A hand-me-down from my father who can’t wear it anymore. It could use a bit of tailoring, but it does look good on me still. I wear it to work all the time. Now, if only I could find a place that sells good quality hats…

19 Greg December 16, 2009 at 11:02 pm

I have to say if you guys are going to buy a coat, you can get older navy pea coats very cheap, I bought an 80′s pea coat for 20 dollars perfect condition, and probably one of the best purchases I’ve made in a while! I looks great and is really warm.

20 Bharat December 22, 2009 at 7:49 am

Always carry a Handkerchief

excellent rule, and basically the first rule of galactic hitchhiking, I’ve always carried a handkerchief since my mum always packed one in pocket when I was 5. I can’t tell you the endless uses and situations where it has come in handy.

@ Daryl
heh I never knew, very ammusing wiki article though

21 Mark Nelson December 22, 2009 at 11:56 pm

I keep having a question pop into my head when I read articles like this: were the old jackets and coats from the early 1900s superior to what we have today despite all the textile engineering, or are we just wimps in the cold now?

It seems like these days, everyone sits and shivers. In old videos, people are out in a coat and a hat, without even gloves, and they’re having the time of their life. What changed?

22 James February 17, 2010 at 12:50 am

“An overcoat does not stand alone – ensure you supplement it with a wool or cashmere scarf & knit hat and insulated leather gloves.”

What??? Who wears a freaking knit cap with a coat and tie and overcoat?? You should be wearing a fedora or a Hamburg, NOT a skiing cap in winter!

23 Carol November 26, 2013 at 2:32 pm

What about warmer climates like Florida? Sweating is not good…

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