The good news is that streetwear has also grown up. So, if you want to change your style or just improve your jeans-and-sweatshirt wardrobe, here are six ways to wear streetwear without looking like you’re trying too hard.
How to Dress for Streetwear
Rule 1: Luxe Up Your Fabrics
Until recently, streetwear clothes were loose enough that you could fall off a skateboard while wearing them. This is why most of them were made of denim and heavy cottons in loose fits. But modern streetwear has moved out of the skatepark, and designers have taken classic pieces like hoodies, cargo pants, and sneakers and made them into clothes you wouldn’t want to wear on the concrete. Streetwear is an odd and complicated thing. On the one hand, it’s cheap, annoying, and often not very good-looking. On the other hand, James Jebbia started the skate brand Supreme, which is now a billion-dollar monster. Even though streetwear started in California’s surf culture 50 years ago, it didn’t really take off until the 1990s, when the first skate boom (thanks to Tony Hawk) and hip-dominance hop’s of the charts turned a whole generation into fans of baggy jeans and graphic t-shirts.
Today, people from that generation are becoming adults. Even though it has a mortgage, it still prefers to wear a hoodie instead of a suit.
“Streetwear is what a lot of people wear every day because dress codes have become so much more relaxed,” says Lara Djandji, a buyer for men’s clothing at Harvey Nichols. “The number of people looking for tailoring has gone down because more and more people wear jeans with a jacket to work, and people who used to wear jeans are now more likely to buy a tracksuit.”
For the average person who wears clothes every day, this means switching from utilitarian fabrics to ones that look and feel better. Olie Arnold, style director at Mr. Porter, says that a pair of high-end sweatpants made of soft materials like cashmere or jersey is a simple way to add a hint of streetwear to your outfit. “They can stand in for a pair of chinos that have seen better days.”
Brands like Loro Piana and Officine Generale now make cashmere baseball caps as well-made as their blazers, and the high street no longer puts loopback cotton in the pyjama section.
Rule 2: Don’t act like a hype beast
In the world of young people, hype is everything. You need to buy brands that your friends already know about, like Supreme, Palace, Gosha, and Yeezy. But over time, the exchange rate changes. Chris Tang, a stylist and photographer, says that there is no age limit for streetwear. “But a guy his age should do what he likes and what works for him.”
The grown-up thing to do is to stay under the radar by wearing innovative streetwear brands that don’t have lines of teenagers outside their stores. “This season, a lot of brands are inspired by streetwear,” says Arnold, pointing to Pop Trading Company’s easy-going urban clothes and Acne Studios’s simple pieces.
In short, you should try to get streetwear outfits without logos or with logos that are small and hidden. Because an adult knows that the best thing about grail finds isn’t shouting about where they came from, but being asked.
Rule 3: Begin at the bottom
“Started from the bottom, now we’re here,” as Drake says. And the man is right. Arnold says, “In streetwear, shoes make the outfit, and sneakers are the key.” But it can be hard to get around in this area. Hype-beasts go crazy every time a new drop comes out, and you can spend a lot of time and money trying to keep up.
Instead of paying the resale price for Yeezys or the latest Off-White collaboration, invest in trainers that will last as long as your brogues by going for high-quality materials and streetwear brands that focus on build quality. “The lines between high-end mainstream fashion and streetwear have become so blurry that they are hard to tell apart,” says Arnold.
Even though purposely “ugly” trainers and chunky soles are becoming more popular, it’s best to avoid decorations or odd details.
Rule 4: Don’t think baggy, think loose
Teenage boys don’t have to worry about their shape, so they can look at clothes that are too big for them. But the loose fits of modern streetwear clothes aren’t kind to people who are getting to be dadbods. Tang says, “Streetwear is, dare I say it, a “lifestyle.” “People from all walks of life can connect with it.” Just make sure it works well for you.
Your best bet is a shape that is less tight than the figure-hugging tailoring of a few years ago but doesn’t make you look like a tent with legs.
The easiest way to do it is below the waist. From high-end to low-end, streetwear brands have switched from slim fits to straight-leg cuts that are easier to move in on a skateboard and more comfortable off one. Teenagers often wear oversized bombers. If you are older, try a cropped jacket to balance out the roominess.
Rule 5: Get the streets to work for you.
Streetwear has spread to every part of men’s fashion, so there aren’t many outfits that can’t be changed to fit the style. Which is good news if you’ve spent the last 10 years building a closet full of soft-shouldered Italian tailoring and don’t want to get rid of it all.
Arnold says that adding streetwear to your work wardrobe can be a little scary. “A hoodie is a simple thing to buy that can change the look of other clothes. For someone who has never worn a hoodie before, I would suggest layering it under a luxurious bomber jacket or a textured, unstructured blazer.
Trainers are another easy way to add a bit of modernity to your office clothes. Arnold adds, “A pair of sneakers with a casual suit or chinos is always a safe and easy choice.”
Rule 6: Make it easy (ish)
A ready-made look is the fastest way to put together a good streetwear outfit. Streetwear is all about mixing and matching pieces from different brands and cultures to show who you are and what you like.
“Don’t show off and wear the newest clothes from head to toe,” says Tang. It’s a look that only Instagram influencers, most of whom are probably too young to drive, can pull off.
That doesn’t mean you can’t wear logo or statement pieces. But as an adult, you should put them with things that are a little more creative. The “it” hoodie that fashion editors have to have goes better with skaters’ chinos (who don’t know what the “frow” is) than with the same brand’s pants and sneakers. If you look like a fashion magazine, tone it down.
Best Outfits Men Can Wear on the Street
Are you looking for ideas for the best streetwear outfits for men? Here are our top picks for outfits that will turn heads and keep you in step with the latest fashions.
Joggers
These days, joggers are the most popular type of streetwear, and they are the best way to put together a stylish but comfortable outfit.
Men who are into streetwear have been wearing all kinds of joggers, from sweatpants to denim to khaki joggers, all of which have the classic tapered ankle and drawstring waist.
Men’s streetwear outfits can be built around joggers. You can wear them with hoodies, bomber jackets, or even a white t-shirt and a casual blazer. You don’t want to miss out on this piece of streetwear.
Cargo Pants
You might think of cargo pants as the perfect outfit for dads, but these practical and versatile pants are a must-have for any streetwear outfit. In recent years, cargo pants have come back into style, but they have always been a part of streetwear culture.
You can put everything you own in the many pockets, but we recommend using a cross-body bag instead of putting too much weight on your pants. They also look great with a lot of different tops.
Pair cargo pants with a polo shirt, dad cap, and bomber jacket for a classic streetwear look for men. Or, instead of the polo, wear a t-shirt with a big logo and a big hoodie.
Big Hoodies
Big hoodies are a big part of streetwear, but there is still a difference between oversized and just plain baggy. When it comes to streetwear, hoodies that are too big are the most popular, as are many other types of loose clothing. Loose clothing still fits you roughly, but baggy clothing will just swallow you up.
Put a loose sweatshirt with tight pants to make your outfit more interesting. The best pants to wear are skinny jeans or straight-leg pants with sneakers or chunky boots to add some thought to your outfit.
Classic Sneakers
It could be said that a man’s classic sneakers are the most important part of his streetwear wardrobe. We’re not talking about sneakers from the first drop, though props if you have a pair or two. We’re talking about sneakers with a classic look. Converse All-Stars, Nike Cortez, Old Skool Vans, and even Jordans finish off a well-put-together streetwear outfit and give it a ’90s vibe.
Classic sneakers can fit into any man’s closet and go with a wide range of outfits. They also have a classic look that will never go out of style. Classic sneakers are a must-have for every man. They can be worn to dress down a suit or to make your streetwear stand out.
Denim Galore
On a red carpet in 2001, Justin and Brittany made the Canadian tuxedo famous. Surprisingly, this look is still popular, especially for streetwear. Even though it’s no longer a fashion faux pas to wear denim on denim, you should still be careful about wearing the same fabric on top and bottom.
For the full denim look, match the wash of your denim jacket to the wash of your jeans and wear a white shirt and dark shoes for a simple look.
To take this streetwear outfit for men one step further and give it a trendy twist, try a black jean jacket with light-washed jeans, or vice versa.
The best thing about denim is that it will probably never go out of style, so having some easy-to-reach-for pieces will make it easy to put together a polished streetwear outfit.
Camo
Camouflage is a bold pattern that fell out of our shopping carts for a while, but now it’s back and better than ever. Camouflage is a big part of streetwear now more than ever, and it definitely makes a man’s outfit stand out.
Most men choose camo pants because they are safe. It’s best if they have a looser fit, but they shouldn’t be so loose that they swallow your whole body. To avoid making an outfit with too many patterns, pair camo pants with solid neutrals like black, tan, olive, or white.
You can also look for jackets with camouflage patterns.
Track suit
Men can wear track suits on the street, and they always have and always will. This simple outfit makes it easy to fit into the streetwear scene, whether it’s a Champion sweatsuit with a matching crew neck and joggers or a classic Adidas track set with stripes.
Instead of spending hours putting together the perfect outfit, just throw on a track suit and a pair of classic sneakers and you’re ready to hit the streets.
Jeans and a Polo
In the world of streetwear fashion, a solid-colored polo shirt with jeans is a classic. Since the beginning of streetwear, the classic look for men has been a polo shirt with simple jeans. So, if you want to really stand out in the world of streetwear, it’s all about how you accessorise this outfit.
Whether you wear clean white kicks or high-top sneakers in a bold colour that goes with (or stands out against) the polo, your shoe choice will take this streetwear outfit to the next level.
You should also think about what kind of jacket or other outerwear to add. To show off the polo, choose something with a zipper or an open front. You can wear a denim jacket, a bomber jacket, or even a casual blazer.
Add a hat to make this look even better. Try a dad hat with a coloured logo, a classic baseball cap, or a bucket hat with a pattern. Lastly, finish off this streetwear outfit for men with some simple chains and a watch made of the same metal.