The 19 Most Stylish Pieces of Men’s Winter Fashion

Dave Bowden

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Man walking on snowy street pulls hat down over his eyes

Thanks to the colder weather and harsher conditions, figuring out what men should wear in winter is surprisingly tricky, particularly for those of us who want to both stay warm and stand out from the (bundled up) crowd.

The problem is that a lot of men’s winter clothes are made for function first and fashion second—and often a distant second, at that.

As a proud Canadian, I know all too well how hard it can be to look sharp and stay warm at the same time.

Like most guys who live in cold climates, I grew up foregoing fashion altogether. I would layer on anything that had the word “Thinsulate” on the label, as long as I thought it would help me survive the winter.

Then, as I started to become more interested in menswear, I went too far in the other direction and insisted on wearing whatever I thought looked cool – warmth and layers be damned – and nearly froze my ass off in the process.

After a lot of trial and error (and a little frost bite), I eventually figured out how to achieve heat and handsomeness in equal measure, and strike a balance between sharp men’s winter style and warm winter clothing.

In this post I’ll share the must-have mens winter fashion pieces worth stocking up on, and help you combine them into sharp mens winter looks that will get your ass noticed, without freezing it off.

The Best Winter Clothes for Men

Breaking Down the Winter Outfits Men Must Have

Men’s Winter Fashion Jackets

Down Parka

Man wearing white down parka
Few pieces of men’s winter clothing combine function and fashion as well as a good parka.

The most stylish options feature fur-lined hoods (although most are faux fur, which looks just as good but doesn’t carry any pesky moral baggage) and either end at the waist or can be cinched there, providing a slimmer-looking silhouette that helps you look more like a roguish arctic explorer and less like Kenny from South Park.

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Leather Jacket

Man wearing brown leather jacket and white sweater

A good leather jacket is not only one of the most masculine pieces you can own, but also one of the most versatile.

When the weather is wet but the temperature’s not quite cold enough for a parka, a leather jacket will both protect you from the elements and project bad-assery (which, let’s be honest, is almost as important).

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Top Coat

Man wearing camel top coat
Top coat image: senivpetro via Freepik

For my money, there’s no piece of men’s winter clothing as dapper as a well-cut top coat (which is why, as I’ve written at length, I’ve spent a truly embarrassing amount of my money on them).

If you intend to layer your top coat (also known as an over coat) over a suit jacket, then buy one a size or two bigger than your suit. So if you wear a 40 suit, consider going for a 42 top coat so that it fits over top.

But if you intend to wear it without a suit underneath, then opt for one in your suit size so that it fits snugly in the shoulders and cuts a slimmer profile.

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Pea Coat

Daniel Craig wearing the Billy Reid peacoat in Skyfall

In addition to top coats, the pea coat is another staple in the stylish man’s winter wardrobe.

Fashioned after the military coats issued to navy seamen (don’t be so immature – that’s seamen, with an “a”), the pea coat is basically the pinnacle of men’s casual winter fashion, and the perfect layer for weekends, first dates or any social activity where you want to look sharp and stylish, but not too “dressed up.”

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Men’s Winter Boots

Cap Toe Boots

Man wearing brown cap toe boots

Cap toes are my preferred men’s boot style for one simple but fundamental reason: they look sharp as hell.

In addition to being stylish, they’re also versatile: you can find sleek, leather-soled cap toes that you could easily pair with a suit, or thick, chunky-soled cap toes strong enough to trudge through snow, ice and sleet. (And if your winters are anything like the ones we get here in Toronto, then I recommend the latter.)

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Chelsea Boots

Man wearing beige Chelsea boots

For men who care about style and fashion but don’t want to forego function entirely, Chelsea boots are a perfect in-between option.

Instead of laces, they sport an elasticized ankle that makes them easy to slide on and off, and helps ensure that no snow penetrates into your socks.

As with the other leather boots on this list, Chelseas range in sleekness and material, but for winter it’s probably best to opt for a rubber-soled leather pair that will still look great (and keep your feet dry) after trudging through snow.

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Wingtip Boots

Black wingtip boots

Wingtips, also known as brogues, owe their origins to English hunting parties, who wore them as they stomped through bogs and fired off shotguns.

But while gentlemen of a different generation wore wingtips to trample through the backcountry, today the modern gentleman uses them to pound the pavement and get him through winter in style.

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Snow Boots

Man walking in Sorel snow boots
Sorel Caribou Boots

I’ll be the first to admit that “snow boots” is a broad term that can apply to various sub-types of men’s boots, but for the purposes of this list, I mean any big, warm, water-proof boot that you could comfortably shovel snow in for an hour or two.

Winter can be harsh, and when the snow on the ground is ankle deep and there’s no sign of a plough in sight, you need something thick, warm and waterproof that may not be dapper, but is damn good at keeping your feet comfy and dry.

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Mens Casual Winter Fashion

Cable Knit (aka Fisherman) Sweater

Chris Evans wearing white cable knit sweater in movie Knives Out

Thick, chunky, masculine and warm as hell, cable knit sweaters are a men’s winter style staple.

They’re perfect for layering underneath any of the coats mentioned above, and when worn alone give off a roguish vibe that evokes grizzled Irish and Scottish fishermen, who finish a hard day’s work at the harbor with a generous dram of whiskey.

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Chunky Shawl Collar Cardigan

Man wearing burgundy shawl collar cardigan

The perfect winter layering piece, a warm shawl collar cardigan can go over top of a t-shirt or henley for a strong casual look, or over top of a button down shirt for a look that’s slightly more dressed up.

The key with these is to make sure they fit slim so that they look like a sweater, not a house coat.

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Turtleneck

Man wearing black turtleneck under beige coat

Turtlenecks might just be the most fashion-forward men’s sweater style, but don’t let their high-style status fool you: they’re also one of the most functional pieces of men’s winter clothing.

A good merino wool turtleneck makes for a great layering piece that can go under blazers, pea coats and top coats (as the photo above so handsomely demonstrates), and can even be worn under a shawl collar cardigan in a pinch. As with cardigans, make sure to keep the fit nice and slim.

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Thin-Wailed Corduroy Pants

Close up of thin wailed corduroy pants
With corduroy pants, the key is to opt for a thin wail, like these ones from Uniqlo

When I was growing up, corduroy pants had a… well, less than stylish reputation, let’s say. At the time, I associated cords with the cheap corduroy jackets I saw at stores like K-Mart (remember K-Mart?), which were warm, but hardly handsome.

Fortunately, corduroy has been reinvented into a slim, stylish but still-warm material that modern men can wear with pride come winter. The key is to opt for thin-wailed cords, meaning the ridges that define the corduroy are narrow and thin, rather than the thick, chunky wails I used to see at K-Mart.

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Wool Scarf

Man wearing wool scarf

When it comes to winter accessories for guys, a warm wool scarf in a neutral color like grey or tan is a must-have.

I go into more detail about this in my post about how to wear rock a scarf, but one thing to keep in mind with scarves is that the bigger and chunkier they are, the more casual they look.

For instance, if you’re wearing a top coat over a suit, you’ll probably want to pair it with a sleek cashmere or merino wool scarf that will look as formal as the rest of your get-up. But if you’re wearing a parka or pea coat, then a thicker knit scarf will complement the more casual look.

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Leather Gloves

Man adjusting leather gloves

A good pair of leather gloves is one of those winter accessories that I wish I had an excuse to wear all year around—there’s just something inherently masculine, stylish and timeless about them.

Opt for a pair lined with a warm fabric like wool to make sure they can carry you from the first chilly night in November through the frigid depths of February, and as always make sure to keep them slim.

Pro Tip:

When wearing leather gloves with leather boots like the kind recommended above, the sharpest move is to match the color of your gloves with the color of your boots. Own a mix of black and brown boots (as you should)? Then when you find a pair of gloves you like, grab them in both colors so you never have to choose between looking sharp and staying warm.

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Toque (a.ka. Knit Hat)

Man and woman wearing winter hats kissing

Before I get to the finer points on how to wear them, a quick – and crucial – note on terminology. What Americans call a “knit hat” or (infinitely worse) a “beanie” we Canadians call by its proper name: a toque. (It rhymes with “Luke,” if you were unsure about the pronunciation.)

OK, with that out of the way, a good toque is a must have for those especially frigid days when ear warmers won’t do. Grab one in a neutral color like grey or tan, and you can easily pair it with just about anything.

As with gloves, you also might want to consider grabbing one in black and another in brown, which you can pair with your boots and gloves for a cohesive and put-together look.

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Newsboy Cap

Man pulling newsboy cap down over eyes in snow

On days when you’re less concerned with keeping your head warm and more concerned with keeping the snow out of your eyes, a newsboy cap is perfect: just as practical as a baseball cap, but about (let me just crunch the numbers here…) four gajillion times more stylish. (Feel free to check my math, but I’m pretty sure that’s right.)

Stick with neutral and earthy colors, like grey and brown, and don’t worry too much about matching the hat with your other accessories; when you keep the cap color neutral, it complements everything else without having to match them.

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Thick Wool Socks

Man pulling on warm winter socks

When it’s freezing cold and the ground is covered in snow, there’s something about sliding your feet into a warm, thick pair of socks that’s simultaneously strengthening and comforting.

Grab a few pairs in various colors, patterns and thicknesses, which come in particularly handy since boot sizes tend to vary, and a size 9 in one brand may feel a lot more snug than size 9 in another.

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Buffalo Plaid Shirt

Man wearing buffalo plaid shirt

Buffalo plaid is the term used to describe simple plaid patterns with big, chunky squares (as opposed to smaller or more intricate patterns), which is most commonly associated with lumberjacks and gruff outdoorsmen.

Because of its association with the great outdoors, you tend to see buffalo plaid used most often on warm flannel pieces, making it perfect for winter, and a great way to add a masculine ruggedness to your casual looks.

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Wrap-Around Ear Warmers

George Clooney wearing ear warmers on movie set

Sometimes in winter you really just need to keep your ears warm, everything else be damned—well, almost everything else. When you’re on your way to an indoor event (or, in Clooney’s case, a pivotal scene), you ideally need a way to keep your ears warm without messing up your hair.

Enter the ear warmers.

Ear warmers may not look great while they’re on, but they’re a great way to avoid frostbite while showing off the handsome contours of your perfectly crafted taper fade.

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You’ve Nailed Mens Winter Fashion

Now Take the Next Step Toward Sharper Style

With the above list in hand, you now know exactly which pieces of men’s winter fashion will help you look sharp and stay warm this winter.

But even though it may sometimes feel like an eternity, the truth is that winter is only one season—and knowing what to wear is only one small part of sharp style.

If I’ve said it once, I’ve said it 1,000 times (and to the annoyance of many): the handsome devil is in the details.

To look your best and out-dress the other guys, you don’t just need to know what to wear in the winter, you also need to know how to nail the details, which add up to make a big difference in your overall appearance.

Enter your email address below and I’ll send you a head-to-toe checklist outlining the Nine Details You Need to Nail, and show you how to use each one to optimize your look and put your best face forward.

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More Resources:
More Men’s Style Advice from Irreverent Gent:
Mens Winter Fashion Trends & Advice from Around Ye Olde Interwebs:

Banner Image Outfits (L to R): Suitsupply | Billy Reid | Bonobos

Dave Bowden

About

Irreverent Gent founder Dave Bowden is a men’s style specialist, an Amazon bestselling author, an unrepentant introvert, a long-suffering (but very patient) Toronto sports fan and the husband of a wonderful (and thankfully even more patient) wife.

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