3 Winter-Friendly Outfits for Every Type of Cold Day (2024)

It's time to layer up.

By Avidan Grossman
3 Winter-Friendly Outfits for Every Type of Cold Day (1)

Every product was carefully curated by an Esquire editor. We may earn a commission from these links.

It's safe to say that, if pressed, most people wouldn't name winter as their favorite season. It's cold. It's wet. It's cold and wet. But you're not most people. See, winter is a fashion-lover's nirvana, and if the opportunity to throw on so many layers you don't know where your coat ends and your body begins isn't making you positively tingle with excitement, you need to step back and reassess your priorities, bro. I'm serious.

If you're not out here trying to look like the meme of Joey from "Friends" wearing a full wardrobe's worth of clothing, you're doing something very wrong. Layering is literally the only good part of the season. Miss me with that "holiday cheer" bullsh*t. The only cheer I need is the sweet, sweet dopamine rush that comes from hitting triple-digit likes on a fit pic I'll probably delete a week later. Skip the holiday card, Grandma, and show your boy some love on the 'gram. This isn't a game.

If you're having trouble feeling inspired, I whittled down your options to three absolutely smacking outfits—each comprised of a grip of cold-weather staples—to offer but a taste of what this season could have in store if you play your cards right. A specially curated medley of winter vibes, if you will. Because as soon as winter hits, the world really is your sartorial oyster—provided your fingers don't fall off before you have the chance hit that "post" button. So, from big-ass parkas to chunky knitwear to the luxest topcoats around (and pretty much every possible layer in between), here's where to begin your search.

Can't wait 'til it's...below arctic temperatures to really start dressing?

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Uniqlo Heattech Knitted Cap

3 Winter-Friendly Outfits for Every Type of Cold Day (3)

Uniqlo Heattech Knitted Cap

Now 40% Off

A vibrant, eye-grabbing beanie ripped straight from the stills of the latest Wes Anderson flick.

Todd Snyder Italian Donegal Twill Balmacaan Coat

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Todd Snyder Italian Donegal Twill Balmacaan Coat

Now 51% Off

To be clear: It's an Italian. Donegal. Twill. Balmacaan. It sort of speaks for itself, doesn't it?

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Dickies Lawrenceburg Vest

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Dickies Lawrenceburg Vest

Now 16% Off

Few icons of workwear-inspired design remain as enduringly stylish asDickies'canvas vest, an all-time layering essential if there ever was one and a perennial MVP of cold-weather dressing.

Bean's classiccable-knit sweater comes in a beefy premiumcotton that'll layer comfortably over or under anything your pair it with.

Gramicci Corduroy Tuck Tapered Pants

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Gramicci Corduroy Tuck Tapered Pants

You seeing this?Examine that sh*t real close, guy.Get up in there. Because this is exactly what your pants should look like right now, and if you don't own a pair like these yet it might be time (read: it's definitely time)to bite the bullet.

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Diemme Suede Roccia Vet Boots

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Diemme Suede Roccia Vet Boots

Now 31% Off

Don't let the fancy Italian pedigree feel you: Diemme's entire MO is centered aroundexpertlycrafted footwear made to withstandthe worst of the elements, and these suede bad boys are no exception.

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Arc'teryx Cerium LT Hooded Down Jacket

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Arc'teryx Cerium LT Hooded Down Jacket

Now 40% Off

Leave it to the outerwear experts at Arc'teryx to craftthe lightweight (850-fill goose down) solution to all your winter layerings problems, sans any of the bulk normally associated with the genre.

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Everlane French Terry Hoodie

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Everlane French Terry Hoodie

Now 51% Off

The hoodie you'll turn to time and time (and time) again.

RAINS Quilted Front Zip Vest

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RAINS Quilted Front Zip Vest

Now 40% Off

Rains' sleek down vest is the layer you should be throwing on over everything you ownbefore you step outside this winter.

The North Face City Voyager Nylon Belt Bag

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The North Face City Voyager Nylon Belt Bag

The North Face knows a things or two about crafting durable cold-weather garms. The brand's belt bag—renderedin a winter-ready, nea-impenetrablenylon—represents the Platonic ideal of what the company still does best: hard-wearing, utilitariangearthat'll see you through the storm, no matter how bad it gets.

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Levi's 550 Light Stonewash Jeans

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Levi's 550 Light Stonewash Jeans

Because the '70s redux is very real, and very relaxed.

Dr. Martens Black Winchester II Boots

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Dr. Martens Black Winchester II Boots

Now 18% Off

An inimitable icon of countercultural style, nowmade all the better by a—very capitalist!—seasonal discount.

3 Winter-Friendly Outfits for Every Type of Cold Day (16)

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Parks Project Yosemite Embroidered Corduroy Baseball Cap

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Parks Project Yosemite Embroidered Corduroy Baseball Cap

Parks Project makes just thetype of crunchy, throwback-inflectedgear you should be reppingin support of one of our country's most famous outdoor spaces.

Aimé Leon Dore x Woolrich Ballistic Parka

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Aimé Leon Dore x Woolrich Ballistic Parka

Now 35% Off

ALD links up withWoolrich for round three of their ongoing collaboration andimbues the latter'scold-weather staples with its signature penchant for retro-inspired designs.

Patagonia Retro Pile Gloves

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Patagonia Retro Pile Gloves

Now 45% Off

Because your fingers deserve to be swaddled in as much fleeceas the rest of your body.

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The North Face Logo-Embroidered Polartec Fleece Jacket

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The North Face Logo-Embroidered Polartec Fleece Jacket

Now 40% Off

Like the one you grew up wearing, but somehow much, muchbetter than you remembered.

Nike ACG Cargo Pants

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Nike ACG Cargo Pants

The certified gorp gods at Nike ACG are back at itagain.

3 Winter-Friendly Outfits for Every Type of Cold Day (2024)
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