The 10 Style Risks You Should Take This Winter

For those of us who aren't living in a tropical paradise, Winter is finally rearing its cold, cold head. Which means it's the perfect time to start rocking all the clothes you've been stocking up on for the past few months. Although it's easy to rely on the tried-and-true layering methods that got you through last season, there's a few new ways to step up your style.

Sure, you can tie a scarf more than two ways, and you might have even started rocking your down vest a little differently, but we're willing to bet there's some winter style choices you haven't tried. To help you add something different to your style this season, here are 10 Style Risks You Should Take This Winter.

MHL Relaxed Fit Shorts
Buy It Now at Mr. Porter, $72

Burton Midweight Pant in Nori Population Print
Buy It Now at Dogfunk, $40

Vans Leather 106 Moc
Buy It Now at Vans, $65

Stylish Japanese dudes have been pulling this look off for the past few seasons, and we think it's about time for it to catch on stateside. Designers like Alexander Wang incorporated similar looks into their collections, and you can easily cop a pair of statement baselayers from brands like Uniqlo and Burton. We'd advise a nice pair of socks and classic sneakers like Vans and a hooded parka to complete the look.

Arc'teryx Rivet AR Glove
Buy It Now at Arc'teryx, $49

Whether you choose to go for a subtle pop like the emerald green gloves this guy is rocking, or full monty with the bright red ones we're suggesting, an easy-to-spot pair of gloves won't only warm your hands — they'll be harder to lose.

Topman Grey Contrast Turnup Chino
Buy It Now at Topman, $60

Corgi Thick Fair Isle Socks
Buy It Now at Epaulet, $60

Just because winter's here doesn't mean you have to stop cuffing your pants. You can still get a leg up with dope, thick socks that'll keep the elements at bay. Get your trousers hemmed so there's no break — meaning they hardly touch the top of your shoe. Or just cuff 'em for the same effect... albeit a little less neat.

Rancourt 5-Eyelet Mid Boot
Buy It Now at Rancourt and Company, $290

Crepe soles are normally reserved for fall months and items like desert boots, but on cold, dry winter days, they'll do their job as well as any other boot would. Consider ditching the chunky vibram soles for a pair of these.

Manastash Mazama Tri-Blend Fleece Jacket
Buy It Now at Hickorees, $236

Ian Velardi Sportcoat
Buy It Now at Park & Bond, $548

You already rock a down vest over your blazer sometimes (and if not, it's a good look), so why not throw an unstructured sportcoat over a fleece jacket or other technical shell? It'll add that extra padding for the winter and you won't need a bulky overcoat.

New Balance 710 Heritage Trail Boot
Buy It Now at The Goodwill Out, $127

Outlier Slim Dungarees
Buy It Now at Outlier, $188

Hiking boots are all over the place right now, but hiking sneakers have been around for a while too. Models like the New Balance 710 and Merrell Eagle Origins successfully meld the rugged look of a hiking boot with the dope colorways and comfort of your favorite kicks. Pair them with great-fitting technical pants like these slim dungarees from Outlier and get trekkin'.

Mark McNairy Camo Painter's Pant
Buy It Now at Mark McNairy, $225

A.P.C. Military Parka
Buy It Now at End, $463

At ease, gentlemen. The trick to rocking camo on camo is to mix up the patterns and colors. Mix up a desert or nautical pattern with the common woodland and jungle prints. People won't see it coming.

Engineered Garments T1 Jacket
Buy It Now at Couverture and The Garbstore, $395

Timberland 6" Premium Scuff Proof Boot
Buy It Now at Eastbay, $150

Publish Henrik Pants
Buy It Now at Publish, $84

Channel 1990s hip-hop cool while still staying relevant by taking the classic uniform of sweats, Timbs, and a bomber jacket and getting the fit right. A trim, not skinny silhouette makes you look great without taking away any of that precious street cred.

10 Deep The Larger Living Beanie
Buy It Now at Karmaloop, $17

Carharrt Bright Lime Acrylic Watch Hat
Buy It Now at Bare Bones Workwear, $7

Stand out this season in an of-the-moment pom beanie, or get a headstart on a new trend with a neon-colored one.

Men's Super Alpine Jacket
Buy It Now at Patagonia, $599

Tuck Knit Ribbed Cardigan
Buy It Now at Gap, $80

Rock a nylon or GORE-TEX coat over a comfortable knit sweater made from a warm fabric like wool. It'll keep you warm while looking fly. Up the ante by pairing bright synthetics with darker knits.