30 Stylish and Warm Men’s Winter Outfits to Wear Now

30 Stylish and Warm Men’s Winter Outfits to Wear Now

Tackle cold weather in style this season

By Megan Collins | Last Updated: Jan 16 2024 | 17 min read

Sometimes the best thing—the only good thing?—about winter is all the stylish and cozy men’s winter outfits.

The layers! The textures! The beards as accessories!

Truly, when it comes to men’s winter fashion, you guys really come out on top. Women have to deal with freezing fashion questions like “Can I wear heels or will I slip on ice and break a bone?” and “Should I wear this dress even though then I’ll have to wear tights?” Because tights are the worst. Men, you have no need for tights, and I hope you appreciate it.

So if you’re looking for men’s cold weather outfit inspiration, you’ve come to the right place. Our team rounded up a whole month’s worth of the best winter outfits for guys to wear now through spring.

Below, check out 30 men’s winter outfits to wear all season long:

Day 1: Let your topcoat do the talking

harryhas winter outfit
image: @harryhas

Wear it well: Dare I say this is the easiest outerwear to style? Throw on a topcoat in a dark color over just about any look, and suddenly, you’re throwing off “male model off-duty” vibes.

So chic!

Day 2: Tan on tan

coastal flicks mens winter outfit
image: @coastalflicks

Wear it well: Sleigh and Clydesdale horses not required to pull off this look.


Day 3: Colorful puffer and a patchwork hat

@yanai.jun1 winter outfit
image: @yanai.jun1

Wear it well: When the weather gives you a serious case of the winter blah’s, that’s the right time to turn up the volume on your winter wear.

RELATED: The Best Winter Coats for Men

You could go with an eye-popping puffer like the one above, or simply sport your favorite, most colorful sweatshirt or sweater to instantly elevate your winter mood.

Day 4: Argyle sweater and a topcoat

laphealsterling mens winter outfit
image: @laphealsterling

Wear it well: This outfit feels so sophisticated, also so easy to wear.

Make it your own with chinos or twill pants in a winter color you love, and whatever pop-of-color sweater (and beanie!) you have in your closet.


Day 5: A field coat for temperate weather

james barley winter outfit
image: @iamjamesbarley

Wear it well: Live somewhere that heavy-duty winter coats aren’t required? You can still look and feel in men’s winter fashion.

RELATED: 5 Days, 5 Ways: The Field Jacket

This country-meets-city wax field coat feels modern with a quarter zip sweater, straight-leg jeans, and ultra-white sneakers.

Day 6: Cardigan in a cool color (and pattern)

mens winter cardigan outfit
IG: @mr.panesar.archived

Wear it well: This whole look is so grunge and 90s and fun. That patterned cardigan?! The boots? The beanie?!?! I mean…

Whether you’re a Gen Z’er who just discovered Empire Records, or an elder millennial who’s ready to wear it for the second time around, get ready to embrace this throwback style for winter.

Day 7: Lumberjack-core

buffalo plaid winter outfit
image: @bigfits1

Wear it well: Dare I say Buffalo plaid is the new black? 

Sure, neutral-hued sweaters like tan, navy, and black may dominate your closet, but as the temperatures drop, consider adding some sunshine to your fall and winter wardrobe.

I love this button-front sweater Diddy wore on a recent Jimmy Kimmel Live! appearance. You could choose something subtler, but why not let your light shine?


Day 8: When all you need is an overshirt

mens shacket winter outfit
image: @out_of_indigo

Wear it well: Just because I’m from Wisconsin and live in New York City doesn’t mean I can’t empathize with those of you for whom an overshirt is all you need from December through March.

Style Girlfriend shares climate-inclusive men’s winter style, y’all!

Which is why this quilted overshirt made the list. If you want a top layer that won’t make you sweat, a shacket will always do the trick.

Day 9: Hunter style in the city

orange beanie winter outfit
image: @fitting_in_now

Wear it well: Hunting is not for me, but the fashion? Absolutely.

Give me a pop of “I’m a person, not a deer” orange! Give me camo! Gimme a vest with a million pockets!

Day 10: Puffer with statement sneakers

black puffer coat winter outfit
image: @tomamadeus

Wear it well: This cold weather outfit looks pretty standard until you get to the shoes. Leopard-print Adidas sneakers? Stunning!

So long as it’s not snowing, this look is totally #SGapproved.

Day 11: Casual workwear style

fleece jacket winter outfit
image: @bchanism

Wear it well: A hoodie and workwear pants? On-trend but maybe nothing special.

Adding a funky sherpa coat? Things just got interesting.

It really can’t get much easier than adding one extra layer to an everyday outfit to help make you look and feel like a winter style star.

Day 12: Go black & blue

plus size mens winter outfit
image: @ethandesu

Wear it well: Black and blue is an underrated color combo for winter.

Whether it’s business casual or weekend athleisure, level up a men’s winter outfit simply by combining this understated, stylish pairing.

Day 13: Ralph Lauren meets Jeff Spicoli

alino who cardigan outfit
image: @alino_who

Wear it well: I love this outfit. The cardigan! The denim jacket! The other cardigan! The sneakers!!

It’s a great example of mixing styles into a look and aesthetic that feels totally unique to you.

Day 14: Vest + Turtleneck + Beret (!)

plus size men's winter style
image: @mohansingphoto

Wear it well: Talk about style! Anyone that can pull off a beret with such confidence gets the #SGapproved stamp of approval.

Not the beret type? Consider switching up your winter headwear from your usual beanie with a bucket hat, flat-brimmed cap, or trapper hat.


Day 15: Double up on outerwear

drake's diary mens winter outfit
image: @drakesdiary

Wear it well: A fleece vest or jacket under a topcoat adds a warm and stylish layer to your winter outfit.

And those pops of color in the hat and socks? Chef’s kiss good!

Day 16: Rep your favorite winter sports team

jake woolf winter outfit
image: @jakewoolf

Wear it well: This look is fun because the wide-leg chinos take the outfit from standard sports fan to stylish sporting enthusiast.

The clompy shoes are a big trend for men, too. Wear them on or off the ice for a winter outfit that just hits different.

Day 17: Dark colors dress up a casual outfit

Wear it well: This subtly stylish men’s winter outfit is giving off-duty CEO who’s getting ready to retire early so he can spend more time with his family.

Understated, comfortable elegance at its finest.

Day 18: Bomber jacket, workwear pants and Dunks

bomber jacket and workwear pants outfit
image: @laytonlamell

Wear it well: A bomber jacket looks good with basically every casual item in your winter closet. The only question is will you freeze your butt off wearing it instead of something warmer?


Day 19: Go with a light-colored puffer

Wear it well: Not all winter outerwear needs to be black! I love this cream puffer jacket for something a little different and unexpected this cold weather season.

RELATED: The Best Puffer Jackets and Vests for Men

Day 20: Pair a DB blazer with a turtleneck

eltondias double breasted blazer outfit
image: @eltondiasreal

Wear it well: Completely obsessed with the high-low mix of this outfit. The turtleneck and double-breasted blazer look seriously stylish, while the jeans and Sambas on the bottom say, “Who needs a drink? Next round’s on me.”

Wear this to your office holiday party. Wear it to your friend’s White Elephant gathering. Just wear it.

Day 21: Throw on a cozy plaid shirt

willhalbert plaid shirt outfit
image: @willhalbert

Wear it well: A classic. What else is there to say?! 

Day 22: Suit up

Wear it well: Blazers really can elevate anything, even a Grateful Dead tee.

When you’re looking for men’s winter outfits that look dressed up without feeling stuffy, this is a great option.

Replace your hoodie and jeans with a suit. Keep the sneakers and t-shirt. You’ll still look professional, just not like everyone else.

Oh, and that over-the-topcoat sweater placement? Elite.

Day 23: Get fashionable in Fair Isle

gentle_baek fair isle vest outfit
image: @gentle_baek

Wear it well: As you know, I am a sucker for a man in Fair Isle.

Wear it as often as you can this winter.

Day 24: Take inspiration from Paddington Bear

Wear it well: More! Men! In! Toggles! This! Winter!

Day 25: Slip into Birkenstocks (with socks!)

ryancascarano winter outfit with birkenstocks
image: @ryancascarano

Wear it well: By now you know that, yes, you can absolutely wear your Birkenstocks with socks.

RELATED: How to Wear Birkenstocks with Everything

So, what’s stopping you from doing it all winter long?

Day 26: Wrap up in a scarf

imdanielsimmons fair isle scarf outfit
image: @imdanielsimmons

Wear it well: Not a balaclava guy?

No worries.

Keep your face warm in a giant scarf instead.

Day 27: Bundle up in workwear

Wear it well: A Carhartt WIP jacket is always a good idea in the winter.

Day 28: Layer, layer layer

03j90 cold weather outfit
image: @03j90

Wear it well: Sometimes you just need a little extra warmth to get you outside on a cold winter day.

A barely there vest just peeking out from your winter coat can get the job done.

Day 29: Layer with Blackwatch

Wear it well: A prime example of how a subtle style upgrade can make a big difference in your winter outfit.

The Blackwatch vest gives an “oomph” to this otherwise standard corporate casual look.

Day 30: Keep it classic

steelojeem cargo pants winter outfit
image: @steelojeem

Wear it well: A warm-ass jacket and your favorite sneakers will always be a good look. Especially on the coldest days.

I started Style Girlfriend to help guys look, feel, and act their best.