8 Go-To Winter Streetwear Outfit Combinations

Make a mental list of streetwear’s key items. Chances are it probably looks a lot like this: hoodie, high-top sneakers, coach jacket, puffer jacket, beanie, and so on. Now, what unites all of those things? Well, aside from the fact that most of it is probably being worn by Gully Guy Leo at this very moment, they’re all particularly well suited to staving off the winter weather in style.

That makes now the perfect time to start introducing more streetwear-inspired styles into your rotation. “Winter is about adding layers,” says stylist Joshua Meredith. “Using streetwear pieces allows for a unique look to be created. The wearer can combine individual pieces that would usually be worn separately, making the overall look something different entirely.”

In other words, not only will the streetwear essentials keep you warm when the weather turns sour, but the melding of styles that the term has become synonymous with presents an opportunity to mix things up and incorporate different elements from across menswear, creating a look that’s all you.

Still, in spite of the flexibility streetwear offers, there are still a few things to bear in mind this season. “Some of the key pieces this season are prints, chunky trainers and the colour beige,” says Meredith. So, with that in mind, here are a few foolproof ways in which you can tick of the trends and wear streetwear right the way through the winter months.

Colorful Flannel + Joggers + Dad Sneakers

Streetwear, at its very core, is about making a statement. And what better way to do that than by donning a vibrant overshirt to cut through the bleak winter weather? A thick flannel version is the perfect choice because not only is it a winter staple, it’s a bonafide streetwear essential, too.

However, there’s always the possibility that wearing a bright flannel shirt with a pair of jeans could see you mistaken for a technicolor lumberjack or time-traveling hipster from 2012. So, in the interest of balance, slap a pair of joggers on your lower half for a more laid-back, street-friendly option.

Last but by no means least, dad sneakers are the comfortable (very comfortable) middle ground that separates Triple S-style beetle crushers from stripped-back, minimalist kicks. They’re perfect for tying almost any outfit together and this one is no exception.


Beanie + Fleece + Jeans

Admittedly, it can be tricky to make a beanie look good. Still, your best chance of success is as part of a streetwear-inspired outfit. Pair a fisherman roll beanie with outdoorsy, yet street-friendly pieces and you can’t go far wrong.

A solid option for your upper half is a fleece. This winter-ready material is having a serious fashion moment at present and it doesn’t look set to slow down anytime soon. Make it slightly oversized for extra points.

Down below, the jeans you spend most of the winter in will do nicely. Mid-wash styles are trending are every bit as nineties as the fleece.

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Dad Cap + Layers + Hiking Boots

These boneless baseball caps are great for keeping the sun off during the warmer months, but that doesn’t mean they ought to be relegated to the back of the wardrobe come winter. The dad cap happens to lend itself nicely to cold-weather clothing, too. Especially where layers are involved.

A good understanding of your layers is key to nailing winter streetwear. Go for garments of varying lengths so that they’re visible when worn on top of one another. And if you’re ever in any doubt about what color to use as your base, you can never go wrong with white.

The finishing touch: a pair of hiking boots. Granted, these may not be your typical streetwear stompers, but then what is “typical streetwear” these days anyway? In fact, luxury hikers have enjoyed a surge in popularity and are creeping (or clumping?) their way increasingly into the streetwear / high-fashion world.


Varsity Jacket + Hoodie + Baggy Trousers

Hoodies were made for layering, as were varsity jackets. Combine the two and you’re well on your way to building an outfit that packs such heat it could melt its way through the iciest of winters. The padded lining of the jacket will keep the worst of the elements out, while the hoodie provides some shelter for your head in the unfortunate event that you should forget to bring a beanie.

The shiny fabric of the jacket is great for adding texture, but to keep things balanced make sure your legwear isn’t fighting for attention. Something, simple, black and baggy will do the trick nicely.


Parka + Wide-Leg Trousers + Chunky Sneakers

When temperatures really begin to plummet, nothing does the trick quite like a heavy-duty parka. Arguably the king of winter coats, this insulated wonder garment is thick enough that it can be thrown straight on over a T-shirt and you should still be warm enough to face even the bleakest of days.

The downside: its puffy appearance means that skinny legwear is out of the question unless you want to look more top-heavy than a Christmas turkey. Instead, opt for a pair of wide-leg trousers in order to keep things balanced.

Those exaggerated proportions extend to your feet, too. Finish the look with a trending pair of chunky sneakers, with enough grip to keep you on point no matter how icy the streets are.


Overcoat + Logo Hoodie + Joggers

Typically, when you think of clothing that pairs with a wool overcoat, your mind will jump straight to tailoring. However, in spite of all the ripped denim and white contact lenses, Kanye West’s wardrobe habits circa 2015 did teach us one valuable lesson: the overcoat works surprisingly well with a hoodie and casual clothing in place of a suit.

Offset the smartness of the coat with a streetwear favorite in the shape of a bold logo hoodie in a contrasting color. Failing that, opt for similar shades to create a tonal look. Or even all black.

Joggers on the bottom in addition to the hoodie could end up a little slobbish if worn on their own, but the presence of the wool topcoat makes it look intentional and brings the look together. In terms of footwear, it’s trainers or bust.


Gilet + Windbreaker + Cross-Body Bag

Simple, functional and stylish, this modular combination is as good as several outfits in one. Layers can be removed or added as temperatures fluctuate. Plus, if the heavens decide to open, the gilet can be worn under the jacket to keep the down out of harm’s way.

On top of that (literally), a cross-body bag will add another layer to the outfit. Not to mention it’s a handy place to stash some gloves and a beanie for when that chill starts to bite.

When it comes to combating anything the weather can throw at you in style, this is the ultimate does-it-all get-up.


Quilted Jacket + Hoodie + Cross-Body Bag

Colder weather doesn’t have to mean sacrificing street cred by shrouding yourself in an overly cumbersome winter coat. Not when your layering game is on point, anyway.

This quilted jacket and hoodie combo is an ideal substitute for a single, heavier piece of outerwear, maintaining a sleek silhouette without sacrificing any of that precious insulation.

Keep things on-trend by opting for earthy, tonal colors like browns, greens and reds, and use a cross-body bag in a contrasting color to help break things up. It might feel alien at first, but once you get a taste of carrying your wallet and keys in something other than your back pockets, you’ll never go back.


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