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The Compass  /  Style  /  Why Men’s Winter Fashion is BS…and What You Should Be Wearing to Work This Winter

Why Men’s Winter Fashion is BS…and What You Should Be Wearing to Work This Winter

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Google “men’s winter fashion” and you’ll find a bunch of pictures of the #menswear crowd in sweaters with their jackets open—or without a jacket at all—on sunny, snow-free streets doing their best to look cool. We call bullshit. In fact, we’ve got a few questions for the arbiters of men’s winter fashion.


When it snows we don’t take snow days,
so what’s with all the casual gear?

The office is still the office and we’ve got to dress for it even when it’s cold outside. The too-cool-for-the-room fashion types may spend their winter days holed up in cafes with their laptops looking like young Jack Kerouacs conjuring up the next scene of On the Road (although we suspect they are actually just teeing up their next Facebook statuses) but the rest of us are steady working our office gigs. We need something that fits the office dress code and won’t have us freezing our asses off. That means a winter suit.

For those who go from home to garage to car to parking garage to hermetically sealed office building you can wear all-seasonal fabrics through all seasons and be fine. But if you commute through harsh conditions and brave the elements for off-site meetings (or lunches), suits made from heartier fabrics can help you to keep the chill off while suiting up. The wool flannel suit you see here looks great altogether for the business formal setting or broken up into separates for a business casual sport jacket or slacks.

Men's Winter Fashion - Highbridge Charcoal Houndstooth Custom Suit by Black Lapel

Is putting on a sweater the best solution to
the problem of dressing stylishly during the winter months?

We don’t think so. When we see all these sweaters, we respond the way Jim Mora responds to questions about the playoffs. Sweaters? You’re showing us sweaters? Now, don’t get us wrong, we’ve got no problem with a stylish sweater—hell, we’ve even celebrated them on this site—but the sweater is a fairly limited weapon of the winter style arsenal for the suit-wearing public. A V-neck can be layered under a suit jacket and help you stay warm. But the chunky, cable knit shawl collared sweaters or the trim cut, graphic crew neck sweaters with their collars rising too high and tight to allow for a tie, are especially difficult to wear if you’re a suit guy.

If you’re looking to shake up your layered look, try incorporating a thin down vest. This vest from Uniqlo’s Ultra Light Down collection stops bone-chilling winds from penetrating your outfit without bulking up your look. Because it doesn’t have sleeves, it easily slides under a even a slim fit jacket giving even your most buttoned up look a touch of modern flair.

Men's Winter Fashion - Ultra Light Down Vest by Uniqlo

The weather in these photos…Where do you think we live?

Seriously, open jackets and sockless chinos on dry sunny streets. Peruse the photos you see when you search for men’s winter fashion and you’ll wonder what happened to winter. For many men winter means trudging to work under gray skies as equally gray snow, shaded by dirty plows and car exhaust, piles up on the sides of icy streets.

We’re not saying that clothes ought to be showcased in dank dreary settings, but let’s get real. Your winter style ought to stand up to winter’s cold and that means you’ll need a good versatile top coat. Single breasted coats that end above the knee in neutral colors like brown, gray and navy blue are formal enough to wear with a suit but still work on the weekend with your more casual clothing. These cold-weather utility players are a crucial part of the dapper man’s winter wardrobe.

Men's Winter Fashion - Double-Faced Cashmere Overcoat by Calvin Klein

Aren’t there any hats a man can wear besides slouchy hipster beanie?

Credit goes to the fashion crowd for understanding that, during the dead of winter, a head covering is a must. But does it have to be the slouchy? What’s next, mandatory beards and thick rimmed glasses? When is the march towards hipster-rule going to be stopped?

While there was a time when no self-respecting white collar worker would be caught dead outside without a fedora, the days of a sea of hat-wearing men crowding the streets of every business district in America are over. We get that. But you can still wear a hat that will keep you warm without taking extreme measures like donning an uber-trendy beanie or an old-school fedora. Enter the newsboy cap (aka the Flatcap or the Gatsby). These hats straddle the line between formal and casual allowing you to wear them with all but the most formal of outfits. We recommend getting one in neutral gray and brown, like this one, to get the most use outs of this winter style staple.

Men's Winter Fashion - Andre Wool Newsboy Cap by Goorin Bros.

Ultimately you’ll define men’s winter fashion in a lot of ways but there’s one man whose style affects you the most, and that’s you. We hope we’ve offered a smart alternative to the prevailing winds of men’s winter fashion but we want to hear from you. Tell us how you’re staying stylishly warm this winter in the comments section below.

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16 thoughts on “Why Men’s Winter Fashion is BS…and What You Should Be Wearing to Work This Winter”

  1. I like the vest idea as it won’t bulk up the arms and there are functional ones out there that don’t add too much bulk. The look carries well and it’s small enough to quickly remove when you get into your office. I’d still prefer the coat over it in my opinion. Being raised on a tropical island, I like full coverage when it comes to cold weather now that I’m stateside.

    Another insightful article again! Call the BS where it is, real men don’t let the elements dictate their lack of style, real men conquer the elements with style.

    1. “Conquer the elements with style.” Love the attitude, Jeremy!

      We’re glad you found this helpful.

  2. I love my Donegal wool flat cap, but I have a real problem with hat hair leading me to keeping it on indoors, at dinner, etc. How do you overcome?

  3. This is a great post. I’ve long seen the #menswear “winter” pictures and questioned if all of these guys live in California… None of the looks I usually see would work in Ontario winters…

    It’s a combo of dressing for the elements and a few cheats that gets you through… The vest is a key layer, on all except the coldest days, I leave the outdoorsy ski jacket at home (when we dip below -20C, I usually bust it out), and tend to layer a down vest, blazer (or some times a cardigan), and then a mac over top and that usually does the trick. The newsboy hat is a good option, but not for extended commutes in real cold where your ears will freeze. Instead of reaching for the floppy toque (sorry, can’t call it a beanie, that would get me deported from Canada…) hipster style, you can get nice tight knit ones that fit your head nicely, cover your ears and look put together and warm, rather than dressed to ride a fixie to the bike polo match…
    As for the footwear issue… here’s where you cheat a little. I wear my hearty redwings (classic moc toes) to and from the office, I can pull them off with work clothes, but I usually change into the brogues that I keep stashed in my office when I get there. In terms of getting salt out of shoes/boots. I find the best is a vinegar water solution, and then rubbing from the inside out of the salt stains. Then once it dries, go through the usual polish routine… The other option if you want to wear your regular kicks is to get shoe covers (some people call them shoe condoms…), like the ones from Swims, that are rubber covers that you can slide on and off for the commute and do the heavy lifting in protecting the shoes from salt/snow…

  4. David Stella says:

    I personally like the “edgy” language.

    Back on topic, I would have loved to see suggested shoes on the post. Wearing the wrong type of shoe in the winter can make your feet feel real cold, and sometimes winter shoes aren’t the most fashionable either.

    1. Black Lapel says:

      Agreed, David, cold weather footwear is a whole can of worms. That’s why we devoted a whole story to it a little while back. We even featured some pretty fashionable options there.

      Of course, if you’re dealing with blizzard conditions a warm pair of socks and a pair of Wellington boots (rocked here by Nick Wooster) will not only keep your feet warm and dry but save your slacks from splashes.

  5. If I’m wearing a wool suit and a cotton shirt, a plastic vest is about the last thing I want to add to look good. The hat and coat are nice, though.

    1. Black Lapel says:

      When the idea first came up, we were skeptical too, but after trying it out, we were sold. Now we get compliments every time we rock ours.

  6. Mike from MA says:

    A good cold blast of common sense and much appreciated. Too much to ask for a similar cleansing on the issue of winter shoes? I’ve seen enough stylists’ fantasies of dandies braving winter in plimsolls or desert boots to ruin my appetite for fashion mags altogether. I live in New England. Our winters are savage: wet, ornery, extended. But I am not wearing Merrells with dress clothes. So what else you got for us? John Varvatos is hawking a beautiful faux-shearling lined brogue boot (so is John Fluevog, for that matter, but in a more surreal color), and you can’t go wrong with a great English shoe with a Dainite sole. But BL always manages to come up with the unexpected, and I’d like to be surprised.

    1. Black Lapel says:

      We hear you, Mike. We’ve covered winter footwear in the past. Those options are good for winter of the not so savage variety. For handling the worst of the worst, we like Wellingtons sported here by Nick Wooster, for handling the snow and slush without ruining the pants of your suits. (How’s that for a surprise choice?)

  7. I like your Compass Journal newsletter and look forward to reading it, but a trend I see in a lot of these kinds of forums is the tendency to use questionable language as a means to sound hip and relevant. Instead of calling “bullshit”, why not call “foul” or pick up a thesaurus and come up with another alternative. This is writing about dressing for a professional or semi-professional environment to a wide audience with sensitivities you can’t be sure of. Keep it appropriate.

    1. Black Lapel says:

      Apologies if we offended, Joe. We try to dish out advice in the spirit of brotherly advice. Our tone may be a bit edgy, and sometimes PG-13, but always true to our brotherly voice.

      1. You (BL) know who your audience is; your audience knows who your audience is–Don’t change a thing.

        1. Black Lapel says:

          Thanks for the kudos. We may not always hit our mark right in the center but we always aim to be in tune with our guys.

  8. The charcoal houndstooth is definitely awesome! I love the patterns and fabrics your team features and uses!

    1. Black Lapel says:

      Thanks, Gavin.

      There’s more where that came from too.

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