The complete guide on how to wear streetwear like a grown-up, plus the best streetwear outfit ideas for men in 2023.
Hey, homie, we’re gonna fix you up with all the most pimped-out swag out there.
No? OK, we can see you raising your eyebrows. We know we’re more of a perfectly coiffed Tan France in this context, but we can definitely give you a few tips to add some edge to your looks with the cool and comfortable aesthetic of streetwear.
Join us as we uncover the unspoken rules of this hip-hop-inspired style and provide examples of streetwear outfits for men.
What is streetwear?
The streetwear trend first cropped up in the ’80s and ’90s alongside the emergence of surf and skate culture, with further influence from hip-hop and underground art scenes. The style was pioneered by everyday people focused on looking cool and feeling comfy.
If that definition seems vague, that’s because it is. Streetwear style is a “you know it when you see it” sort of thing, but common elements include graphic tees, flashy sneakers, distressed denim, and oversized everything.
With the rise of the modern internet, street fashion soon crossed over into the mainstream. The 2000s blogging boom saw style bloggers, such as Hypebeast, FaceHunter, and The Sartorialist, who captured the style of the common person and influenced the fashion industry.
Now, avant-garde takes on casual hoodies, cargo pants, and classic shell toes appear in the pages of Vogue, and high-fashion men’s streetwear brands like Off-White and Vetements sell $500 T-shirts. If all that sounds intimidating, don’t worry; you’ll be a street-style fashionista when we’re through with you.
How to wear streetwear without looking tacky
The recent increase in remote working has made casual dress much more prevalent in the fashion landscape (let’s take a moment to remember how busted we all looked during lockdown). Now that you have to go outside and interact with other humans once in a while, you probably don’t want to give that up. Fortunately, streetwear clothing can elevate your lazy-day looks if you follow some basic guidelines.
Of course, fashion is a form of creative self-expression, so if you feel strongly about wearing something, you do you, boo. But these rules will help when you’re going for the streetwear aesthetic:
Invest in quality
Casual doesn’t necessarily mean cheap. Low-quality clothing fits poorly and only lasts a few wears, guaranteeing you’ll spend more in the long run to replace it.
That doesn’t mean you need to break the bank, however. Workwear brands, such as Carhartt and Dickies, offer plenty of affordable clothing that will last until you enter your silver fox phase. It’s no wonder they’re staples of the streetwear subculture.
If you are splurging on high-cost investment pieces, look for the heavyweight construction, practical outdoor materials, and technical fabrics often favored by Japanese designers.
Don’t be a fashion victim
After widespread popularity in the 2010s, logomania returned with a vengeance in 2021. Designers like Gucci, Fendi, and Louis Vuitton were slapping loud, maximalist monograms on absolutely everything.
But you don’t need to be a label loyalist or a tryhard. Following the hype and going overboard with designer duds will only make you look like a cringe-fest — not to mention it's super expensive.
Keep it age-appropriate
No one’s saying you have to start wearing cardigans and deck shoes once you hit 25, but if you’re dressing like a kid caught smoking under the bleachers, it’s time to update your style. Your teenage years were bad enough; they don’t need to be recreated.
Brands like Acne Studios, APC, and Rick Owens are great at doing streetwear that those pesky kids aren’t interested in. But if you want to avoid spending all the arms and legs you’ll be putting into those clothes, workwear is a timeless choice.
Good shoes take you to good places
Many stylists assert an outfit begins with a pair of shoes. That’s especially true of streetwear, which shares a lot of DNA with sneakerhead culture. If you’ve forked out for an awesome pair of high tops and want to get your money’s worth, don’t be afraid to build your wardrobe around them (more on that below).
Watch the silhouette
Oversized, baggy fits hang on a twink like he’s a coat hanger, but they just don’t work on guys with a bit more bulk. And there’s no shame in that; nothing’s hotter than a thick daddy who knows how to dress himself. Beautiful, burly boys may want to grab a cropped jacket rather than a bomber and opt for more fitted trousers.
Keep it simple
Unless you’re Iris Apfel or a crazy bag lady, this is a rule for life. You don’t need every beanie, jacket, and plaid shirt out there — just a few essential pieces to mix and match. Add slick accessories, such as a crossbody bag or a subtle chain necklace, to spice things up.
Keep it neutral
Finally, neutral colors are always a safe bet to ensure your pieces work year-round and fit your existing wardrobe. Neons and pastels have a time and place (especially in the avant-garde world of streetwear), but they’re difficult to match and won’t wash well.
A pop of color can make an outfit shine. Just remember, this isn’t the NYC Pride March; there’s no need to bust out the entire rainbow.
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10 streetwear outfits for men in 2023
The best way to build an outfit is to start with garments you love to wear. In that vein, we’ve provided some outfit ideas centered around staple streetwear items that will work with the things you already own.
The specific items you choose are up to your personal taste. Classic streetwear brands, such as Vans, Stüssy, and Nike, will always deliver, but most luxury brands offer streetwear as part of their primary or diffusion lines, too.
1. The perfect sneakers
The foundation of any streetwear outfit. No matter how street you’re dressed, if you’re wearing a pair of worn-down brogues, it’s giving Newsies. Whether classic or cutting-edge, your kicks are best displayed using stark contrast. Wear all-black sweats with white Nikes or pair muted neutral cargo pants with brightly colored Pumas.
2. The quality joggers
No athleisure wear is more practical than a solid pair of joggers. Thom Browne, Michael Kors, and every other upscale designer offer luxe versions that riff on the gym staple. They pair nicely with a matching hoodie for a monochrome ’fit. Layer on a jean jacket to look extra rugged.
3. The jeans that last
Denim is the common thread throughout countless aesthetics, streetwear included. Like sneakers, they’ll be the cornerstone of your wardrobe and never go out of style. Think wider and baggier than what you’re used to; maybe not full-on JNCOs, but something that recalls those hot boys you used to thirst after at the park. They go great with graphic tees and bucket hats.
4. The cargo pants
The army’s influence is ubiquitous in fashion — just ask your local leather daddy. In the realm of streetwear, cargo pants in heavyweight materials are super versatile. Check out Carhartt and Alpha Industries for classic skater styles or brands like Nike and The North Face to achieve a more grown-up vibe. Wear them with a pullover, a chain, and some high tops for a look that’s equal parts cozy and cool.
5. The utility vest
These are an excellent way to experiment with layering. Just be sure to go for something laid back and nonthreatening; the tacticool SWAT team vibe is very 2018. Try wearing an earth-tone canvas vest over a sweater or open-collar shirt for an eye-catching clash of preppy and street aesthetics.
6. The graphic tee
OK, we know we told you not to overdo it on the logos, but one solid graphic statement is permitted. Classic brands like Calvin Klein and Gucci are safe options, but some time-worn musician merch or a quirky thrift find is even better. You can always dial it down with an open shirt and light-wash jeans.
7. The simple hoodie
Not just for napping on the couch, hoodies are perhaps the most iconic streetwear staple. You can wear them with anything on this list, but they work just as well with tapered trousers and a peacoat. Cozy, functional, and perennially stylish, they’re the ultimate sartorial expression of relaxed rebellion.
8. The bucket hat
It looks rad and protects you from the sun. Your mother would be proud. Use it to top off a simple outfit — such as a tank top and baggy cargo pants — to say, “I put effort into looking this chill.” Throw on an oversized pair of shades to add a layer of mystery. Is that an incognito celebrity, or just a stylish stud?
9. The thick flannel plaid shirt
You might think of a plaid shirt as a lumberjack-meets-hipster cliché, but it’s also a great building block for streetwear-inspired wardrobes. Think less like Paul Bunyan and more like Kurt Cobain. Resilient and adaptable to any climate, flannels are often worn open over a hoodie or tee.
10. The puffer jacket
More than a utilitarian garment for hikers and climbers with a penchant for The North Face, puffer jackets offer the ideal oversized swagger for streetwear — plus, it feels like wearing a down comforter. The puffier, the better; you want to feel like a sexy version of the Michelin Man (or maybe you already find him hot, we don’t judge). Choose one in jet black or a bold hue, and let it stand out as the star of a more muted getup.
Time to up your game
Now that you’re all dripped out, you’ll have all the fashion-forward fellas dripping, too. Whether it’s on the streets or between the sheets, find a crew to ride with among the 10 million monthly users on the Grindr app.
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