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25 Winter Style Essentials

Beanies, big coats, boots, boot socks and so much more.

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By Evan Malachosky

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Whenever cold weather arrives wardrobes contract. We transition from wearing things because we like how they look to wearing things because they’ll keep us warm — with the occasional sacrifice to emphasize the former. Largely, though, it’s an “I’ll wear whatever works” time of year. But that doesn’t mean you must always sacrifice style in order to survive sub-zero temperatures.

Our list of winter style essentials balances form and function, meaning the items here are as high-performing as they are nice to look at. That includes plush beanies that won’t pill, jackets with eco-friendly fill, boots that won’t falter in a foot of snow, gloves to keep your hands dry and fingers from cracking and plenty more.

Admittedly, finding these things can be hard. Perhaps the coat you really want looks amazing and all but wouldn’t keep you warm on a crisp fall morning, let alone nighttime in the dead of winter. It’s why we stick to what works, often longer than we should — or long after the look’s gone out of style. So, whether you’re bolstering your winter wardrobe or building it from scratch, these selections represent 25 different ways to upgrade — in colors correct for the season, too.

Winter Essentials for Men

These trousers balance the comfort and warmth of sweatpants with the look of something more structured.

Flint and Tinder fuses the comfortability of a compression sock with the warmth of a wool sock. 

Embrace an era of outdoor gear bygone with J.Crew’s retro-tinged Hiker Boots.

A sleek, simple beanie that’ll last a dozen seasons.

Free from tags and logos, this Yak sweater is reversible. One side is brown with tidy stitching and the other is lighter with more deconstructed finishings.

The ideal middle layer, Wallace & Barnes’ Shirt Jacket makes a statement (and will keep you warm).

Sure, you could splurge on a $750 dollar parka, but Columbia has a long history of making super solid outerwear — and their option is only $179.

Double knit means double the warmth — especially if this is your primary base layer.

Filson makes a massive collection of classic winter gear. The Mackinaw Cape Coat, with its wool body and classic pattern, proves no exception.

Upgrade your sweatpants ahead of winter. These won’t let the cold winter wind whip through them.

Our top ranked snow boot, the Sorel Caribou Street looks like something dressier but wears like a hard-working winter boot.

Filson’s Goatskin gloves come in three colors, Black, Tan and Saddle. These are the tan option.

The Tipped Lambswool Gloves: simple, soft gloves you can stuff in your coat pocket. 

Your wardrobe can’t be 99-percent outerwear with nothing to wear underneath it. Buck Mason’s Thermal Surplus Tee is the perfect starting point.

Contrary to popular belief, the original Bean Boot could indeed get better. The shearling-lined version solves my number one complaint when wearing them: my feet won’t feel cold anymore!

Brunt the most brutal stretch of winter in this windproof Nobis parka.

At last, luxe socks. And by Japanese brand RoToTo nonetheless.

Don’t like scarves? Need a way to cover your neck still? Slip into this Alex Mill turtleneck, which comes finished with a traditional fisherman cable knit.

Because this option’s made from wool, it’s plenty warm but also breathable, meaning it’s a smart layer in the dead of winter and a solid top layer once spring hits.

Although the peak for fall foliage has passed, this Bulky Watch Cap embodies the season’s most impressive color. 

Handspun and -dyed, Chamula’s Double Cuff beanie comes with a Fair Isle pattern that pays tribute to Northern Scotland in colors that reference rich Mexican traditions.

Scarfs are extra, yes, but don’t underestimate their ability to trap in heat.

Some slippers are far too flimsy for actual wear — like to and from the mailbox or into the backyard to bring your dog back inside. UGG’s Tasman Slippers are not. They have a significant sole and a super simple look about them. 

Not a big fan of boots? Corridor’s City Hiker can tackle similar terrain, but it wears like a sneaker. 

There’s no material more classically fall and winter than corduroy.

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