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The Wall Street Publication > Blog > Style > How To Put on Streetwear Like A Grown-Up | Fashion
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How To Put on Streetwear Like A Grown-Up | Fashion

Editorial Board Published May 20, 2025
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How To Put on Streetwear Like A Grown-Up | Fashion
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Males’s Vogue Guides
Males’s Vogue Traits

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Streetwear is an odd and sophisticated beast. On the one hand, it’s disposable, obnoxious, and sometimes unflattering. On the opposite, Supreme – the skate model that James Jebbia launched – is now a billion-dollar behemoth. Although born 50 years in the past in Californian surf tradition, streetwear outfits didn’t really blow up till the nineties, when the primary skate increase (thanks, Tony Hawk) and hip-hop’s chart dominance turned a technology onto dishevelled denims and graphic tees.

In the present day, that technology is hitting maturity. And although it may need a mortgage, it nonetheless feels extra snug in a hoodie than a go well with.

“Streetwear is so many people’s go-to each day because dress codes have become so much more relaxed,” says Harvey Nichols menswear purchaser 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.”

Thankfully, streetwear itself has grown up, too. So whether or not you’re trying to alter your fashion, or simply refine your jeans-and-a-sweatshirt wardrobe, listed below are six methods to put on streetwear outfits with out wanting like a try-hard.

The Guidelines of Streetwear Outfits
Rule One: Luxe Up Your Materials

Streetwear clothes have been, till just lately, issues you might fortunately fall off a skateboard whereas sporting; therefore why most have been rendered in denim and heavy cottons, in non-constrictive matches. However fashionable streetwear fashion has stepped out of the skatepark and designers have reworked time-honored items – hoodies, cargo trousers, trainers – into clothes you wouldn’t need to threat on the concrete.

In the present day, for the on a regular basis wearer, which means upgrading utilitarian materials to one thing extra premium. “An easy way to incorporate a subtle element of streetwear is through a pair of high-end sweatpants,” says Mr Porter fashion director Olie Arnold, referencing kinds reduce from soft-handle supplies like cashmere and jersey. “They can substitute for a well-worn pair of chinos.”

It’s a transfer that’s been endorsed throughout the board, from manufacturers like Loro Piana and Officine Generale, who now craft cashmere baseball caps as well-made as their blazers, to the excessive avenue, which now not stuffs loopback cotton into the pajama part.

Rule Two: Don’t Be A Hype Beast

For youth tradition, hype is all the pieces. Recognition is forex, so it’s essential cop the manufacturers that your friends find out about: Supreme, Palace, Gosha, Yeezy. However the trade fee modifications 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 transfer is to fly below-the-radar, by sporting streetwear labels which might be progressive however don’t have youngsters queued up outdoors their shops. “A lot of brands this season are taking influence from streetwear,” says Arnold, who factors to easy-going city wares from labels like Pop Buying and selling Firm and stripped-back items from Pimples Studios.

Briefly: it’s best to intention to get streetwear outfits with out the logos, or no less than hold them tucked away as refined particulars. As a result of an grownup is aware of the most effective factor about grail finds isn’t shouting about the place they’re from, however being requested.

Pop Trading Company streetwear outfitsPicture Credit score: Pop Buying and selling Firm
Acne Studios streetwear outfitsPicture Credit score: Pimples Studios
Rule Three: Begin From The Backside

Within the phrases of Drake: “Started from the bottom, now we’re here.” And the person’s bought some extent. “In streetwear, shoes make the outfit, and sneakers are the lynchpin of it all,” says Arnold. However this may be harmful terrain to navigate. Hype-beasts hyperventilate over every new drop, and you’ll make investments grotesque quantities of time (to not point out cash) making an attempt to maintain up.

As an alternative of paying the resale worth for Yeezys or the newest Off-White collaboration, spring for trainers that may final so long as your brogues by favoring premium supplies and streetwear manufacturers that prioritize construct high quality. “The lines between luxury mainstream fashion and streetwear have blurred beyond recognition for a number of seasons now,” provides Arnold.

Regardless of the rise of purposely ‘ugly’ trainers and chunky soles, it’s sensible to keep away from adornment or odd shapes to ensure your box-fresh kicks will look pretty much as good together with your go well with as your joggers.

Rule 4: Assume Unfastened, Not Dishevelled

Teenage boys don’t have to stress their silhouette, to allow them to afford to browse the outsized rail. Nonetheless, the free matches of recent streetwear outfits aren’t forgiving to these getting into their dadbod part of life. “Streetwear is, dare I say it, a ‘lifestyle’,” says Tang. “It resonates with people from all walks of life.” Simply be sure you get it best for you.

Your greatest transfer is a silhouette that’s extra relaxed than the figure-hugging tailoring of some years in the past however doesn’t make you seem like a tent with legs.

It’s best to tug off beneath the belt. Streetwear manufacturers from the high-end to the excessive avenue have swung from slim matches to straight-leg shapes that supply extra motion on a skateboard – and are extra snug off one. An outsized bomber is a teenage accompaniment; for these older, strive a cropped jacket to stability out the looseness.

Carhartt streetwear outfitsPicture Credit score: Carhartt
Edwin streetwear outfitsPicture Credit score: Edwin
Rule 5: Carry The Streets To Work

“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 one other easy solution to make your workplace togs a contact extra up to date. “A pair of sneakers with a relaxed suit or chinos is always a safe and easy option,” provides Arnold.

Herschel streetwear outfitsPicture Credit score: Herschel
Reiss streetwear outfitsPicture Credit score: Reiss
Rule 6: Hold It Easy(ish)

The swiftest path to a profitable streetwear outfit is a glance straight off the shelf. Streetwear is in regards to the mix-and-match; items from totally different manufacturers and cultures that collectively mirror your individual allegiances and pursuits.

“Don’t go flashy and wear head-to-toe the latest gear,” says Tang. It’s a glance that solely works for Instagram influencers, who’re most likely all nonetheless too younger to drive.

That’s to not say you’ll be able to’t rock assertion or emblem items. However as a grown-up, it’s best to pair them with stuff that exhibits a bit extra creativity. The ‘it’ hoodie that’s a must have for vogue editors works higher with chinos extra readily seen on skaters (who don’t know what the ‘frow’ is) than trousers and sneakers from the identical model. If you happen to’re dressed like a lookbook, dial issues again.

Gucci streetwear outfitsPicture Credit score: Gucci
Stussy streetwear outfitsPicture Credit score: Stussy
Finest Streetwear Outfits for Males

Searching for some inspiration in terms of the most effective streetwear outfits for males? Listed below are our high picks for head-turning outfits that may hold you consistent with immediately’s newest tendencies.

Joggers

Today, joggers are on the forefront of streetwear and are the prime constructing blocks of a snug, but putting outfit.

Within the context of streetwear, fashion-forward males have been sporting joggers of all types, from sweatpants materials to denim and even khaki joggers, with the basic tapered ankle and drawstring waist.

Joggers is usually a basic base of a streetwear outfit for males… Pair them with hoodies, bomber jackets, or perhaps a informal blazer with a white t-shirt. That is one streetwear staple you don’t need to forego.

Reiss streetwear outfitsPicture Credit score: Reiss
Cargo Pants

Whilst you might consider cargo pants as the final word dad outfit, these sensible but versatile trousers are a staple of any streetwear outfit. The cargo pant has actually skilled a resurgence lately however has all the time had a stable place in streetwear tradition.

Not solely are you able to match all the pieces you personal within the a number of pockets (although we advocate utilizing a cross-body bag, moderately than weighing your pants down), however they give the impression of being spectacular with a variety of tops.

For a basic streetwear outfit for males, strive matching cargo pants with a polo shirt, dad cap, and bomber jacket. Or swap out the polo for a daring emblem tee and outsized hoody.

orSlow streetwear outfitsPicture Credit score: orSlow
Large Hoodies

Large hoodies are on the heart of streetwear, although there’s nonetheless a distinction between outsized and straight-up dishevelled. With regards to streetwear, outsized hoodies reign supreme, as do all kinds of free clothes. Unfastened clothes nonetheless roughly matches your type, whereas dishevelled garments will merely swallow you entire.

Pair your free sweatshirt with tighter pants to create a distinction in your outfit. Skinny denims or straight-leg trousers work greatest, paired with sneakers or chunky boots for some thought behind your outfit.

Adidas streetwear hoodiePicture Credit score: Adidas
Traditional Sneakers

There’s arguably no extra essential element of a person’s streetwear assortment than his basic sneakers. We’re not speaking from the unique drop, per se, (although kudos if you happen to’ve bought a pair or two), however sneakers in a basic fashion. Converse All-Stars, Nike Cortez, Outdated Skool Vans, and even Jordans are the cherry on high of a put-together streetwear outfit and add the ’90s feeling to any outfit.

Past including a timeless fashion to your look, basic sneakers can match into any man’s wardrobe and be worn with an enormous vary of outfits. From dressing down a go well with to creating your streetwear stand out, basic sneakers are a must have for any man.

Vans streetwear outfitsPicture Credit score: Vans
Denim Galore

Whereas Justin and Brittany made the Canadian tuxedo well-known on a 2001 pink carpet, this look is surprisingly nonetheless in fashion, particularly within the streetwear context. Denim on denim isn’t taboo anymore, however it’s best to nonetheless be cautious about sporting the identical materials on high and backside.

For the complete denim look, match the wash of a denim jacket to your denims and pair with a white shirt and darkish sneakers for a minimalist feeling to your outfit.

To take issues a step additional and put a stylish spin on this streetwear outfit for males, strive totally different coloured denim, like a black jean jacket with gentle washed denims, or vice versa.

The perfect half about denim is it’s unlikely to ever exit of favor, so having some straightforward to succeed in for items will aid you assemble a cultured streetwear outfit with ease.

Levi's streetwearPicture Credit score: Levi’s
Camo

Whereas camoflauge undoubtedly fell out of our procuring carts beforehand, we’re right here to say this daring sample is again and higher than ever. Camo is an integral a part of streetwear, now greater than ever earlier than and positively helps a person stand out in his outfit alternative.

Most males go for camo pants, that are a secure alternative. It’s greatest to have them in a looser match (tapered ankles work, too), however not so free that they swallow your body entire. Match camo pants with stable neutrals like black, tan, olive, or white to keep away from creating an outfit that’s too busy, pattern-wise.

You too can hold a watch out for jackets in camo print.

Stussy streetwear outfitsPicture Credit score: Stussy
Monitor Fits

Monitor fits have and all the time might be a suitable streetwear outfit for males. Whether or not it’s a full Champion sweatsuit with matching crew neck and joggers, or a basic stripped Adidas observe set, this easy getup makes becoming into the streetwear scene a breeze.

Reasonably than spending hours placing collectively the proper outfit, throw on a observe go well with with a pair of basic sneakers and also you’re able to hit the streets.

Sergio Tacchini streetwear outfitsPicture Credit score: Sergio Tacchini
Polo with Denims

A stable coloured polo shirt with denims is nothing in need of basic on the earth of streetwear vogue. From the daybreak of streetwear, the pairing of the polo and easy denims has remained an iconic search for males. That stated, it’s all about the way you decorate this getup to actually stand out on the earth of streetwear.

Whether or not you throw on a pair of unpolluted white kicks or high-top sneakers in a daring colour that compliments (or contrasts) the polo, you shoe alternative will take this streetwear outfit to the subsequent degree.

You’ll additionally need to take into consideration what sort of jacket or outerwear to throw into the combo. It’s greatest to decide on one thing with a zipper, or an open entrance to indicate off the polo. A denim jacket, bomber, and even informal blazer works right here.

A hat will improve this look even additional, so check out both a dad hat with a coloured emblem, basic baseball cap, or a patterned bucket hat. Lastly, pair with some easy chains and a watch in the identical metallic and also you’ll be unstoppable on this streetwear outfit for males.

Stussy streetwear outfitsPicture Credit score: Stussy
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