Winter Clothes for Men: 37 Cold-Weather Essentials You Need This Season

Substantial wool trousers made of a tweed or Donegal wool are perfect for keeping your gams warm while adding texture to your cold-weather fits. Toss 'em on with a shaggy sweater, a puffer, and hiking boots.

Adding wool sole inserts is a little hack that will save your little piggies from frostbite, and you won't worry about losing them in the laundry, unlike your sock collection.

Blundstones are the classic winter daily driver: they look great with every outfit, and can handle most winter situations, what with being thick-lugged and water-resistant. Don't be surprised if you spend more time in these boots than you do anything else for the next four months.

Bad hair days don't exist when you've got a good beanie.

Cuffing season or not, it's time to switch up your daily fragrance to something a bit warmer, like this mesmerizing cologne from Byredo. Bergamot top notes get sweetened by rum and fig, and followed by the cozy scent of tonka beans. (And if you're still searching, check out our favorite winter colognes and our favorite spicy colognes.)

Scarves should be long enough to wrap around your neck, wide enough to fold into a makeshift hood, and patterned enough to be the star of the show.

That said, we always have a plain solid scarf in the rotation when we need to protect our neck and protect a fit that's already speaking at a high volume. (Scout out more of our favorite men's scarves over here.)

If your version of winter is more wet than snowy, or the heavy wool coat is a bit overkill, pull on a classic trench. It'll work with—and keep dry—everything in your closet. (And we've got all our favorite trenches together, if you want some options.)

Champion hoodies are as sturdy and warm as they were almost a hundred years ago.

Pop this over a waffle-knit thermal, pull on some flannel-lined jeans, and you'll be the coolest, coziest guy around.

Warm up without bulking up.

In winter, even your jeans have a base layer of their own.

Sure, these Uggs are great for scuffling around your apartment, but they'll look pretty sick with a baggy pair of cargos and a big puffer if you get tempted to take them for a walk. (And you should.)

Your curated collection of rings will completely understand if you have to cover them up with a nice set of gloves. (We've also got our favorite touchscreen-ready gloves lined up if you're not trying to miss a minute of the groupchat.)

The bag is the one essential piece of kit that won't keep you warm in the winter. Get yourself something with texture, an eye-catching color (preferably both), and make sure it's got a strap long enough to wear on your shoulder so you don't have to subject your hands to the biting cold.

Bomber jackets were originally made to withstand the subzero temps that World War II pilots experienced at high altitudes. That insulation is still plenty useful and stylish even you're only piloting an SUV.

The cardigan: a cozy staple and a layering hero. And as we've said before, the best cardigans make a statement.

We'll be seeing less of your graphic tees this time of year, so lean into really good knitwear that has a great texture.

You'll be inside a lot these next few months, and you're thinking you need a fresh pair of sweats. Scoop up a heavyweight pair with a clean silhouette, and they'll look as good in the daylight as they do on movie night.

Buck Mason's team-up with Eddie Bauer pulled some of the outdoor legend's greatest hits from the archives. This heavier-than-it-looks quilted jacket is a quiet reminder that E.B. has a whole album's worth of greatest hits.

If it was good enough for The Beach Boys, it's good enough for you.

Worn with a flannel shirt, or a cardigan, or under a top coat, a mock neck sweater like this will keep your neck warm without looking like everyone else's basic crewneck.

Corduroy pants. Need we say more?

Hiking boots like these from Diemme have both the grit to handling grueling climates and the sauce to juice up any outfit, whether it's a laidback jeans-and-trench look, a trail-ready gorp getup, or something more avant garde.

All the elements that postal workers have to face just to deliver our packages and credit card offers—rain, sleet, snow, and combinations of the three—have no chance against a waterproof Gore-Tex shell like this Arc'teryx Beta jacket.

Waffle-knit thermals keeping your core nice and toasty, but they also look great peaking out from underneath a flannel or even a short sleeve graphic tee.

Keep your feet warm and your fits anchored with a pair of wool socks.

Make sure you've got a pair of weatherproofed kicks to give your feet a break from all the heavy-duty winter boots you'll be chained to for the season.

Wearing a sport coat with jeans is your unstoppable style hack for everything from casual Fridays to visiting the in-laws during the holidays.

Styled with a button-up shirt, a simple tee, or (if you've been hitting arms day) by itself, a good sweater vest will roll with just about any situation.

A blue striped shirt is the do-everything button-up you should have in your sartorial arsenal. It can add some variety and pattern to a drab outfit, or clean up nicely for more dressed-up occasions.

A deep pile fleece jacket is like a cup of soul-warming coffee you can wear.

These days, hoodies are more than just fleece billboards for your favorite sports teams. Take advantage of that.

Don't muck about when it comes to your winter footwear rotation. As much as some beautiful suede hikers or Gore-Tex sneakers can handle a little precipitation, you need to have some real boots for wading through the worst of it.

Your flimsy cotton chinos aren't gonna cut it in winter unless you've got a pair of heat-retaining long underwear to help out.

A zippy knitwear situation like this full-zip knit from Stone Island works all sorts of ways: unzipped to show off your graphic tee, halfway open like a V-neck cardigan, or fully closed like a sporty track jacket.