How To Wear Streetwear Like A Grown-Up

Men's Fashion

Streetwear is a strange and complex beast. On the one hand, it’s disposable, obnoxious, and often unflattering. On the other, Supreme – the skate brand that James Jebbia launched – is now a billion-dollar behemoth. Though born 50 years ago in Californian surf culture, streetwear outfits didn’t truly blow up until the nineties, when the first skate boom (thank you, Tony Hawk) and hip-hop’s chart dominance turned a generation onto baggy jeans and graphic tees.

Today, that generation is hitting adulthood. And though it might have a mortgage, it still feels more comfortable in a hoodie than a suit.

“Streetwear is so many people’s go-to each day because dress codes have become so much more relaxed,” says Harvey Nichols menswear buyer Lara Djandji. “The amount of customers looking for tailoring has decreased as more and more people are wearing jeans with a jacket to work, and those who previously wore jeans are now more inclined to shop for a tracksuit.”

Fortunately, streetwear itself has grown up, too. So whether you’re looking to adjust your style, or just refine your jeans-and-a-sweatshirt wardrobe, here are six ways to wear streetwear outfits without looking like a try-hard.

The Rules of Streetwear Outfits

Rule One: Luxe Up Your Fabrics

Streetwear clothing were, until recently, things you could happily fall off a skateboard while wearing; hence why most were rendered in denim and heavy cottons, in non-constrictive fits. But modern streetwear style has stepped out of the skatepark and designers have reworked time-honored pieces – hoodies, cargo trousers, trainers – into garments you wouldn’t want to risk on the concrete.

Today, for the everyday wearer, that means upgrading utilitarian fabrics to something more premium. “An easy way to incorporate a subtle element of streetwear is through a pair of high-end sweatpants,” says Mr Porter style director Olie Arnold, referencing styles cut from soft-handle materials like cashmere and jersey. “They can substitute for a well-worn pair of chinos.”

It’s a move that’s been endorsed across the board, from brands like Loro Piana and Officine Generale, who now craft cashmere baseball caps as well-made as their blazers, to the high street, which no longer stuffs loopback cotton into the pajama section.

Rule Two: Don’t Be A Hype Beast

For youth culture, hype is everything. Recognition is currency, so you need to cop the brands that your peers know about: Supreme, Palace, Gosha, Yeezy. But the exchange rate changes over time. “There isn’t an age cut-off for streetwear,” says stylist and photographer Chris Tang. “But an older guy should stick to what they like and what works for them.”

The grown-up move is to fly below-the-radar, by wearing streetwear labels that are innovative but don’t have teenagers queued up outside their stores. “A lot of brands this season are taking influence from streetwear,” says Arnold, who points to easy-going urban wares from labels like Pop Trading Company and stripped-back pieces from Acne Studios.

In short: you should aim to get streetwear outfits without the logos, or at least keep them tucked away as subtle details. Because an adult knows the best thing about grail finds isn’t shouting about where they’re from, but being asked.

Pop Trading Company streetwear outfits
Image Credit: Pop Trading Company
Acne Studios streetwear outfits
Image Credit: Acne Studios

Rule Three: Start From The Bottom

In the words of Drake: “Started from the bottom, now we’re here.” And the man’s got a point. “In streetwear, shoes make the outfit, and sneakers are the lynchpin of it all,” says Arnold. But this can be dangerous terrain to navigate. Hype-beasts hyperventilate over each new drop, and you can invest grotesque amounts of time (not to mention money) trying to keep up.

Instead of paying the resale price for Yeezys or the latest Off-White collaboration, spring for trainers that will last as long as your brogues by favoring premium materials and streetwear brands that prioritize build quality. “The lines between luxury mainstream fashion and streetwear have blurred beyond recognition for a number of seasons now,” adds Arnold.

Despite the rise of purposely ‘ugly’ trainers and chunky soles, it’s wise to avoid adornment or odd shapes to guarantee your box-fresh kicks will look as good with your suit as your joggers.

Rule Four: Think Loose, Not Baggy

Teenage boys don’t need to stress their silhouette, so they can afford to browse the oversized rail. However, the loose fits of modern streetwear outfits aren’t forgiving to those entering their dadbod phase of life. “Streetwear is, dare I say it, a ‘lifestyle’,” says Tang. “It resonates with people from all walks of life.” Just make sure you get it right for you.

Your best move is a silhouette that’s more relaxed than the figure-hugging tailoring of a few years ago but doesn’t make you look like a tent with legs.

It’s easiest to pull off below the belt. Streetwear brands from the high-end to the high street have swung from slim fits to straight-leg shapes that offer more movement on a skateboard – and are more comfortable off one. An oversized bomber is a teenage accompaniment; for those older, try a cropped jacket to balance out the looseness.

Carhartt streetwear outfits
Image Credit: Carhartt
Edwin streetwear outfits
Image Credit: Edwin

Rule Five: Bring The Streets To Work

Streetwear’s tendrils have crept into every corner of menswear, which means that there are now few outfits that can’t be adapted to the look. Which is good news if you’ve spent the last decade cultivating a wardrobe of soft-shouldered Italian tailoring and are loathe to toss it all out.

“Incorporating streetwear into your [work] wardrobe can be a tad intimidating,” says Arnold. “A hoodie is a simple item to invest in that can transform more traditional attire. For an amateur hoodie-wearer I would recommend using it for layering; try under a luxe bomber jacket or textured unstructured blazer.”

Trainers are another simple way to make your office togs a touch more contemporary. “A pair of sneakers with a relaxed suit or chinos is always a safe and easy option,” adds Arnold.

Herschel streetwear outfits
Image Credit: Herschel
Reiss streetwear outfits
Image Credit: Reiss

Rule 6: Keep It Simple(ish)

The swiftest route to a successful streetwear outfit is a look straight off the shelf. Streetwear is about the mix-and-match; pieces from different brands and cultures that together reflect your own allegiances and interests.

“Don’t go flashy and wear head-to-toe the latest gear,” says Tang. It’s a look that only works for Instagram influencers, who are probably all still too young to drive.

That’s not to say you can’t rock statement or logo pieces. But as a grown-up, you should pair them with stuff that shows a bit more creativity. The ‘it’ hoodie that’s a must-have for fashion editors works better with chinos more readily seen on skaters (who have no idea what the ‘frow’ is) than trousers and sneakers from the same brand. If you’re dressed like a lookbook, dial things back.

Gucci streetwear outfits
Image Credit: Gucci
Stussy streetwear outfits
Image Credit: Stussy

Best Streetwear Outfits for Men

Looking for some inspiration when it comes to the best streetwear outfits for men? Here are our top picks for head-turning outfits that will keep you in line with today’s latest trends.


These days, joggers are at the forefront of streetwear and are the prime building blocks of a comfortable, yet striking outfit.

In the context of streetwear, fashion-forward men have been wearing joggers of all sorts, from sweatpants material to denim or even khaki joggers, with the classic tapered ankle and drawstring waist.

Joggers can be a fundamental base of a streetwear outfit for men… Pair them with hoodies, bomber jackets, or even a casual blazer with a white t-shirt. This is one streetwear staple you don’t want to forego.

Reiss streetwear outfits
Image Credit: Reiss

Cargo Pants

While you may think of cargo pants as the ultimate dad outfit, these practical yet versatile trousers are a staple of any streetwear outfit. The cargo pant has certainly experienced a resurgence in recent years but has always had a solid place in streetwear culture.

Not only can you fit everything you own in the multiple pockets (though we recommend using a cross-body bag, rather than weighing your pants down), but they look impressive with a wide range of tops.

For a classic streetwear outfit for men, try matching cargo pants with a polo shirt, dad cap, and bomber jacket. Or swap out the polo for a bold logo tee and oversized hoody.

orSlow streetwear outfits
Image Credit: orSlow

Big Hoodies

Big hoodies are at the center of streetwear, though there’s still a distinction between oversized and straight-up baggy. When it comes to streetwear, oversized hoodies reign supreme, as do a wide variety of loose clothing. Loose clothing still roughly fits your form, while baggy clothes will simply swallow you whole.

Pair your loose sweatshirt with tighter pants to create a contrast in your outfit. Skinny jeans or straight-leg trousers work best, paired with sneakers or chunky boots for some thought behind your outfit.

Adidas streetwear hoodie
Image Credit: Adidas

Classic Sneakers

There’s arguably no more important component of a man’s streetwear collection than his classic sneakers. We’re not talking from the original drop, per se, (though kudos if you’ve got a pair or two), but sneakers in a classic style. Converse All-Stars, Nike Cortez, Old Skool Vans, and even Jordans are the cherry on top of a put-together streetwear outfit and add the ’90s feeling to any outfit.

Beyond adding a timeless style to your look, classic sneakers can fit into any man’s wardrobe and be worn with a huge range of outfits. From dressing down a suit to making your streetwear stand out, classic sneakers are a must-have for any man.

Vans streetwear outfits
Image Credit: Vans

Denim Galore

While Justin and Brittany made the Canadian tuxedo famous on a 2001 red carpet, this look is surprisingly still in style, especially in the streetwear context. Denim on denim isn’t taboo anymore, but you should still be cautious about wearing the same material on top and bottom.

For the full denim look, match the wash of a denim jacket to your jeans and pair with a white shirt and dark shoes for a minimalist feeling to your outfit.

To take things a step further and put a trendy spin on this streetwear outfit for men, try different colored denim, like a black jean jacket with light washed jeans, or vice versa.

The best part about denim is it’s unlikely to ever go out of style, so having some easy to reach for pieces will help you construct a polished streetwear outfit with ease.

Levi's streetwear
Image Credit: Levi’s


While camoflauge definitely fell out of our shopping carts previously, we’re here to say this bold pattern is back and better than ever. Camo is an integral part of streetwear, now more than ever before and certainly helps a man stand out in his outfit choice.

Most men opt for camo pants, which are a safe choice. It’s best to have them in a looser fit (tapered ankles work, too), but not so loose that they swallow your frame whole. Match camo pants with solid neutrals like black, tan, olive, or white to avoid creating an outfit that’s too busy, pattern-wise.

You can also keep an eye out for jackets in camo print.

Stussy streetwear outfits
Image Credit: Stussy

Track Suits

Track suits have and always will be an acceptable streetwear outfit for men. Whether it’s a full Champion sweatsuit with matching crew neck and joggers, or a classic stripped Adidas track set, this simple getup makes fitting into the streetwear scene a breeze.

Rather than spending hours putting together the perfect outfit, throw on a track suit with a pair of classic sneakers and you’re ready to hit the streets.

Sergio Tacchini streetwear outfits
Image Credit: Sergio Tacchini

Polo with Jeans

A solid colored polo shirt with jeans is nothing short of classic in the world of streetwear fashion. From the dawn of streetwear, the pairing of the polo and simple jeans has remained an iconic look for men. That said, it’s all about how you accessorize this getup to really stand out in the world of streetwear.

Whether you throw on a pair of clean white kicks or high-top sneakers in a bold color that compliments (or contrasts) the polo, you shoe choice will take this streetwear outfit to the next level.

You’ll also want to think about what kind of jacket or outerwear to throw into the mix. It’s best to choose something with a zipper, or an open front to show off the polo. A denim jacket, bomber, or even casual blazer works here.

A hat will upgrade this look even further, so try out either a dad hat with a colored logo, classic baseball cap, or a patterned bucket hat. Finally, pair with some simple chains and a watch in the same metal and you’ll be unstoppable in this streetwear outfit for men.

Stussy streetwear outfits
Image Credit: Stussy

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