The 21 Most Stylish Pieces of Men’s Winter Fashion

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Thanks to the colder weather and harsher conditions, figuring out what men should wear in winter is surprisingly tricky.

And that’s particularly true for those of us who want to both stay warm and stand out from the (bundled up) crowd.

Man walking on snowy street pulls hat down over his eyes
When you know what to look for, even a snowy city street can become a showcase for sharp style

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.

If I thought it would help me survive the cold, long days of the winter season, I would throw on anything that had the word “Thinsulate” on the label.

Then, as I started to become more interested in menswear, I went too far in the other direction:

I 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 this holiday season, 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.

Easily one of the warmest top layers available, 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.)

Parkas either end at the waist, like a puffer jacket, or extend down to the thighs.

My favorite ones extend past the waist but can be cinched around it, providing a slimmer-looking silhouette that helps you look more like a roguish arctic explorer and less like Kenny from South Park.

Top Picks:

Check out our in-depth Alpha Industries parka review to find out how their N3B parka performed through the depths of a Toronto winter.


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.

Admittedly, a leather jacket isn’t always thought of as a winter coat.

But when the temperature is too cool for a bomber jacket but not quite cold enough for a parka, a leather jacket will both protect you from the elements and project bad-assery.

(And let’s be honest: for most of us, projecting bad-assery is almost as important as keeping warm.)

Top Picks:

Check out our full review of The Jacket Maker to find out how their (handsome-ass) flight jackets hold up in Canadian conditions.


Top Coat

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

While a heavy coat like a parka may be warmer, for my money a well-cut top coat is the single most important piece in a man’s winter wardrobe.

(Which is why, as I’ve written at length, I’ve spent a truly embarrassing amount of money on them.)

Just as a leather jacket can replace a bomber during the colder months, a top coat can replace a trench coat when the rainy days turn into snowy ones.

If you intend to use your top coat (also known as an over coat) as an outer layer that goes 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.

In terms of color, neutral colors like grey and beige (or camel) tend to be your best bet because they’re so versatile.

But if you’re looking for something a little bit more formal, darker colors like navy and black also are also good options.

Top Picks:

Pea Coat

Chris Pine rocked a pea coat to perfection in All the Old Knives

In addition to top coats, the pea coat is another staple that’s perfect for everyday wear.

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.

It’s the perfect layer for weekends, first dates or any social activity where you want to look sharp and stylish, but not too “dressed up.”

Top Picks:

Men’s Winter Boots & Shoes

Crossovers

Winter crossovers

A cross between a shoe and a boot, the (aptly named) crossover is arguably the perfect footwear for winter.

It combines the high-ankle support and warmth of a boot with cushioned insole and rubber outsole of a sneaker, giving you the best of both worlds.

Plus, shoes with a chunky white sole happen to be very in right now, making crossovers a perfect marriage between function and fashion.

Top Picks:

Cap Toe Boots

Man wearing brown cap toe boots

Cap toes are my favorite men’s boot style for one simple but fundamental reason:

They look sharp as hell.

But in addition to being stylish, they’re also versatile.

You can find sleek, leather-soled cap toes that look just as sleek as dress shoes, or ones with thick, chunky rubber soles 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.)

Top Picks:

Check out our full Thursday Boots review to find out how their cap-toe Captain boots hold up in real-world conditions.


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.

Top Picks:

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 gent uses them to pound the pavement and get him through winter in style.

Top Picks:

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.

Snow boots may not be dapper, but they’re damn good at keeping your feet comfy and dry.

Top Picks:

Mens Casual Winter Fashion

Cable-Knit Sweater

Chris Evans wearing white cable knit sweater in movie Knives Out

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

They’re a perfect middle layer for wearing underneath any of the coats mentioned above.

Or, you can wear them alone, and give off a roguish vibe that evokes grizzled Scotch-Irish fishermen, who finish a hard day’s work at the harbor with a generous dram of whiskey.

Top Picks:

Chunky Shawl Collar Cardigan

Man wearing burgundy shawl collar cardigan

While a lot of guys reach for a comfy hoodie come winter, a shawl collar is just as comfortable – and a lot more stylish.

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.

Top Picks:

Why just wear a shawl collar when you could rock one?
We’ve put together a complete guide to making shawl collar sweaters look sharp as hell.


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 wear.

A turtleneck made from thicker fabrics like cashmere or merino wool will help seal in your body heat, keeping your body temperature warm without requiring a super thick technical jacket from brands like Patagonia or North Face.

That makes it great for layering under more stylish options like blazers, pea coats and top coats, as the photo above so handsomely demonstrates.

And for extra warmth, they can even be worn under a shawl collar cardigan in a pinch.

But remember: as with cardigans, make sure to keep the fit nice and slim.

Top Picks:

For more swagger-worthy sweaters, check out our round up of the (absolute) most stylish types of mens sweaters.  


Thin-Wailed Corduroy Pants

Close up of thin wailed corduroy pants
With corduroy pants, the key is to opt for a thin wail, like the kind pictured here

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.

Modern corduroy pants are perfect if you tend to wear slim-fit or skinny jeans in fall and spring, but need something a little warmer for 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 (and cheap-looking) wails I used to see at K-Mart.

Top Picks:

Warm 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.

Top Picks:

Acetate Sunglasses

Look, I love a good gun-metal aviator as much as the next guy.

(Actually, if you’d ask my wife, she’d tell you I love aviator shades way more than any sane person would or should.)

But come winter, the last thing you want to do is wrap a cold piece of metal around your face.

That’s why winter is the best time to rock a classic pair of stylish acetate frames.

In addition to keeping your face a little warmer, acetate frames tend to be sturdier than thin metal sunglasses, so they’ll hold up better when you go in doors and shove them in your coat pocket.

Top Picks:

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?

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.

Top Picks:

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.

Top Picks:

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, newsboy caps are perfect:

Just as practical as baseball caps, 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.

Top Picks:

For more great looks inspired by the Peaky ([email protected]!) Blinders, check out our roundup of the best Peaky Blinders suits that combine their timeless, classic style with a modern, contemporary aesthetic.


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 merino wool socks that’s simultaneously strengthening and comforting.

Grab a few pairs in various colors, patterns and thicknesses.

(And don’t be afraid to have some fun with the sort of bright colors you normally wouldn’t choose in winter!)

Having a range of thicknesses will come in handy when wearing winter boots, since boot sizes tend to vary, and a size 9 in one brand may feel a lot more snug than size 9 in another.

Top Picks:

Buffalo Plaid Shirt

Man wearing buffalo plaid shirt

Buffalo plaid is the term used to describe the kind of flannel shirts that have simple plaid patterns with big, chunky squares.

(As opposed to the smaller or more intricate checkered patterns that you usually find on a dress shirt, which aren’t really thought of as winter fabrics.)

In most people’s minds, Buffalo plaid is most c ommonly associated with lumberjacks and gruff outdoorsmen.

Because of that association, you tend to see buffalo plaid used most often on warm flannel pieces like thick button-downs, and even outer layers like jackets and coats.

That makes it perfect for cold winter months, and a great way to add a masculine ruggedness to your casual looks.

Top Picks:

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 haircut.

Enter the ear warmers.

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

Top Picks:

You’ve Nailed Mens Winter Clothes

Now Take the Next Step Toward Sharper Style

Now that you’ve read our men’s winter style guide, you know how to make your cold-weather style look sharp as hell.

But even though it may sometimes feel like an eternity, the truth is that winter is only one season—and knowing how to put together smart winter outfits 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 Fashion Advice from Irreverent Gent:
Mens Winter Fashion Trends & Advice from Around Ye Olde Interwebs:

Banner Image: Photo by Dorota Zietek / Shutterstock, Illustration by Irreverent Gent

About

Dave is a men's style blogger whose insightful (and of course, irreverent) advice on how to look good and live well is read by more than two million people each year.

When not obsessing over style and self-improvement, he can usually be found at home playing with his wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

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