The 10 Style Risks You Should Take This Winter

Image via Complex Original

Jean Shop Dry Selvedge Denim Jacket
Buy It Now at Mr. Porter, $320 

Your denim jacket looks great over a hoodie when the autumn weather is crisp, but when the temperature drops even further, it actually turns into one of the most versatile layering pieces in your wardrobe. Don't be afraid to throw it underneath a parka or sportcoat as some extra rugged insulation.

ASOS Chelsea Boots
Buy It Now at ASOS, $56

This footwear was made popular by The Beatles, and while it hasn't necessarily fallen out of style, it's safe to say they aren't as popular as they used to be. Menswear collections have been attempting to revive this style for the past few years, and we think this is the season they start coming back into prominence. Don't be surprised to see a lot more of these popping up soon, which why we'd advise hopping on the trend now—so you can say you were up on it first.

Utility Sweatpant
Buy It Now at J. Crew, $60

Last winter, dudes wore running sneakers with everything. With the growing trend of mixing comfort and style, sweatpants have been reinvented with a slimmer fit, shorter cuffs, and more pockets. That means you can wear them with just about anything, and we think you should. Throw them on under a duffle coat, wear them with an untucked oxford shirt and denim jacket above. Just be sure to wear them with sneakers. Sorry, sweatpants and proper footwear still doesn't look good.

G.P.P.R. Clash Denim Shirt
Buy It Now at Metro Park, $124

Here's one style risk you can actually DIY. Take a white oxford and dip-dye it in some indigo. Voila, there's your new go-to shirt. The indigo-dyed shirt has been popping off in numerous collections, from obscure Japanese brands like Nepenthes and Blue Blue Japan to streetwear brands like G.P.P.R. Like the love child of chambray and last season's tie-dye craze, there's a wabi-sabi sort of charm to these shirts. We're not sure how long this trend's sticking around, but we do think it looks damn cool.

Rick Owens Oversize White T-Shirt
Buy It Now at Ssense, $227

All right, we know most guys aren't willing to rock the kilt like Kanye. However, we do fully advocate messing with proportion. That means you can feel free to take the tall tees out from storage and throw them on under the hoodies you're still rocking today, or wearing them with slim fitting pants at the bottom. Designers like Robert Geller and Rick Owens have made this drapey/slim silhouette something of an aesthetic trademark, and rappers like A$AP Rocky have helped cement it as a part of the "street goth" look they constantly sport today. Is it for everyone? Definitely not, but hey, it might work for you.

Alexander Wang Band Collar Shirt
Buy It Now at Barneys, $120

No collar? No problem. The band collar—or mandarin collar, balances out the classiness of a button down shirt but eschews the need for neckwear. The result is a clean looking garment you can wear under jackets, sweatshirts, and sportcoats for a tailored look that doesn't scream preppy—so you can keep your street cred intact.

484 Selvedge Jean in Wheat
Buy It Now at J. Crew, $155

You know by now that the old rule about white pants don't matter. Regardless of your opinions on white denim, it can't be denied that when done correctly, it can look awesome. The key is to make them look like any other pair of jeans you'd throw on. Too often, guys make the mistake of treating them too precious or trying to make them be the focal point of an outfit. Here, they work because they're paired with a brown houndstooth blazer, suede boot, and a scarf with pops of color. Despite the color of the pants, the texture and pattern of the blazer still attracts your eyes the most.

Blackwatch Flannel Robe
Buy It Now at Vermont Country Store, $50

Wanna take your "cozy boy" style to the next level? Wear a flannel robe as an unstructured topcoat. You can't rock the terry cloth ones you stole from the hotel pool, the fabric has to be smooth and relatively thick. That's why we advocate going for a wool flannel fabric in something bold yet classic, like blackwatch plaid. The wintery print won't look out of place when you walk outside, and when paired with straight-cut pants, an untucked shirt, and the right attitude, people will think you look awesome instead of like you just rolled out of bed.

The Decades Nightvision 5-Panel
Buy It Now at The Decades, $35

Navy Polka Dot Scarf
Buy It Now at Topman, $15

Venture outside the solid and plaid scarf spectrum with a timely pattern like polka dot. 5-panel hats are pretty much the norm these days, and plenty of companies like The Decades and Fairends are making versions in awesome prints like camo, tribal-inspired, and other all-over prints. Step up your style by rocking them both at the same time, but be sure to keep some solid colors between the two to provide some harmony in your kit. Otherwise it can be a little overwhelming. It goes without saying that if you're trying to pull this off, the rest of your clothes should be relatively subdued.

Baldwin Ryan Trouser in Washed Camo
Buy It Now at Baldwin, $189

While they look awesome with a pair of sneakers or Tims, consider taking camo pants out of the streetwear context and dressing them up with a tweed or navy sportcoat and an oxford shirt. You'll need a more tailored cut in the pants to pull this off well, and Baldwin Denim's Ryan pant offers a nice slim, straight cut that's nowhere near skinny. Dockers Alpha Khakis just dropped a bunch of affordable camo options as well. Finish off the kit with a pair of plain-toe oxford shoes or saddle shoes to keep it grounded in the casual realm.