Style Risks to Take This Winter

Suede outerwear in the winter is one of the most impractical things you can wear. The odds of it getting dirty and/or wet are very high, which can obviously ruin it. But it’s a price you should be willing to pay to look dope, right? Bombers are killing it right now, with some brands taking the risk of making suede versions for you.

Beanie hats and 5-panels are reliable, but when has reliability been fun? Bucket hats are a traditional warm-weather staple, but the wool variety could definitely switch the style up for you this winter. May seem risky because it doesn’t directly cover your ears, but the warmth will assuredly surprise you. It’ll add a little street cred to whatever you’re wearing, too.

Don’t just dress like a mountain man. Become the mountain man. The outdoorsy menswear wave is taking over, mixing fleeces, cargo pants and high-tech boots with some streetwear nuances for what should be dubbed “mountain man swag.” Toss in a frothy beard and your winter style risk is complete.

Don’t store away those Flyknits just yet, friend. They or any lightweight running shoe can still see the light of day for some of these colder winter times. As long as you have a pair of thick, cozy wool socks to pair them with, it doesn’t matter how thin the fabric (or lack thereof) is.

Your wool-bodied, leather-sleeved traditional varsity jackets will forever be a staple of style, but brands are taking it a step further with some creative materials and variations. Throw in some snakeskin or pick up a varsity jacket with the body of a pea coat to have everyone scratching their heads in wonderment and asking how this stylish man traveled back in time from the future.

Yes, we know that Kanye has been rocking long military-style coats pretty steadily for a few months now. All the reason for you to take that risk you know your stylish counterparts are too chickenshit to take the plunge. Military parkas and pea coats that come up a few inches from the ground will alter your silhouette, and if the exaggerated look puts you off at first, just wait until people start treating you with the deference reserved for badasses.

It makes sense. You're walking around outside and you need to protect precious things: an extra pair of shoes, laptop, bagged lunch. All sacred. A winterized backpack is not only fashion-forward, but utilitarian. Quilted, leather or waxed canvas will definitely leave a lasting impression, and when was the last time you could ever say that about an accessory? A dope, winter-ready backpack will definitely set yourself apart from the basics of the world.

The leather craze is starting to die down to appropriate levels, which we’re sure cows everywhere are thankful for. But leather bikers and moto jackets are most definitely classics that won't ever fully go away. This winter, try tossing one over a light denim shirt or, better yet, a jacket for that concentrated mix of two staple style fabrics. The juxtaposition of the two is definitely a risk, but the double jacket may cause heads to explode. Proceed with caution.

It's certainly easier to pass through the day in a pair of Timbs or Red Wings to keep the area between your sole and lower shin toasty, but an exaggerated hightop sneaker is an unexpectedly dope look this winter. Choices are bountiful now that big boys like Rick Owen, Maison Martin Margiela, and Umit Benan have made the unorthodox look a normal addition to collections this winter. And when your buds ask why you opted for sneakers instead of boots? Stomp them out with your new, steezy kicks.

Who doesn’t love a good exaggerated layer these days. It's an unexpected but welcome switch-up from the normal look dudes put on. Now it's time to put a winter spin on this and turn that oxford or poplin tunic into flannel for some warm weather layering on the long side. Layer with a regular length jacket for a juxtaposition most people can’t fathom pulling off. This is a style risk that will undoubtedly get gawked at, but that's what pushing boundaries and stunting is all about.