fall and winter style essentials


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

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Watch Cap

Filson’s Wool Watch Cap will keep you warm — that I can guarantee.

Hudson Aran Jumper

Everyone needs a classic cable knit sweater. 

Eco Nordic PrimaLoft Field Parka

J.Crew’s Eco Nordic Field Parka comes with faux fur trim and an Econyl (aka regenerated nylon) body.

Textured Jogger Pants

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

Winter Pass Printed Fleece

Printed fleeces are typically too expensive to bother monitoring. I just know that they’ll never fall to a price I feel is affordable. But Columbia’s done it. The Winter Pass Printed Fleece isn’t $500 bucks. Not even $100 — just $95!

Pachena Bay Hiker

For tough (snowy, icy) terrain you need tough boots.

Brushed Wool Shirt-Jacket

Wallace & Barnes

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

Crew Sweater

Kotn’s classic Crew Sweater is back by popular demand.

Dolphin Cord Overcoat

Our Legacy

Overcoats are cool. Corded overcoats, though? Even cooler.

Nordic Waterproof Hiker Boots

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

Pavel Faux Shearling Jacket

A.P.C.’s Pavel Jacket is 100-percent vegan: The body is polyester while the collar is faux sheepskin. 

Original Lined Goatskin Gloves

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

Vintage Thermal Surplus Tee

Buck Mason

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.

Cashmere Cuff Beanie

Get this steal of a soft Cashmere Cuff Beanie in three colors.

Whiting Shirt

Wax London

Don’t wait to buy one of Wax London’s heavy Whiting Shirts. They rarely last long.

Tasman Slipper

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. 

Reversible Brushed Mohair Sock

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

Bulky Watch Cap

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

Shearling-Lined Bean Boot

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!

Goose Down Alpine Puffer Jacket

The Arrivals

This jacket makes going outside in the frigid cold surprisingly palatable. 

Plaid Cashmere Scarf

Joshua Ellis

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

Wool Camp Socks

Flint and Tinder

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

City Hiker

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

Tipped Lambswool Gloves

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

Flat Front Taper Corduroy Pants


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

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