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Top winter fashion trends for men in 2021
Find on-trend clothing for men that doesn't cost a fortune.
Menswear this winter is all about heft, warmth and a wink of fun, with corduroy and flannel in big supply. To really nail the 2021 mood, try not to take dressing up too seriously — a little rumple never hurt anyone, and an oversized fit will give you more room to play.
Pro tip: For high-quality clothing made by smaller, luxury design houses, shop the standout brand listed beneath each trend.
1. Cargo all over
Utility was all over the runways for fall/winter 2021, and that means you’ll find lots of pockets on this season’s trendiest pieces. We’re loving shirts and pants that basically come with extra room for snacks.
- Engineered Garments
Hermanos Koumori Nothing Chore Jacket
Dual Drawstring Cargo Pants
Worker cargo jacket
2. One-and-done pattern play
More is more this season when it comes to men’s shirts and jackets, with solid colors on hold for true trendsetters. This men’s winter fashion trend is a clear throwback to the ’90s. Go for a shirt that combines two colors — or if you’re feeling bold, a shirt with multiple plaids.
- Thom Browne
90s oversized shirt in mix and match green
Classic Fit Rose Print Shirt
Greg Lauren check-pattern panelled shirt
3. Weather-ready flannel
Flannel as a wintertime trend isn’t anything new, but we’re giving it the spotlight anyway. This season, we’re seeing oversized buffalos checks and plaids, along with big pockets piggy-backing off the cargo trend. Fair warning: your significant other might like your flannel shirt even more than you do.
- Alex Mill
Brushed flannel overshirt in brown tartan plaid
Pendleton Men's Long Sleeve Classic Fit Board Wool Shirt
Plaid Hooded Jacket
4. Grown-up corduroy
Shirts in this sturdy fabric are totally in this season and look best when layered over a graphic tee. If you’ve got bad memories of super stiff corduroy from your grade school years, rest assured this fabric has evolved since then, with looser, lightweight corduroy driving the trend. Go for 100% cotton for a corduroy shirt that softens even more over time.
Reclaimed Vintage Inspired corduroy overshirt in khaki
Corduroy Chest-Pocket Jacket
Finamore 1925 Napoli corduroy long-sleeved shirt
5. Sole-full kicks
Men’s shoes come with extra sole this winter, in bright colors and interesting designs instead of the regular black rubber that you’re used to. This men’s winter trend applies pretty much across the board, to sneakers, boots, oxfords and even dress shoes.
Converse Bosey-MC Hi Gore-Tex sneaker boots in malted
Lace-up boots in black faux leather with double strap detail
Balmain BBold chunky sneakers
6. Pants with pleating
Yes, you read that right — pleated pants are back for men this season. But to avoid looking like your biology professor, choose dark navy and olive green instead of tan or khaki, and look for a hemline that hits your ankle. We love pleated pants with a poppy, patterned button-down shirt. Top with corduroy if you’re feeling retro.
If you can’t bring yourself to embrace the pleats, dip your toe into the trend with a pair of drawstring trousers.
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