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How to Level Up Your Streetwear Game

CEO Tinh Phung
Streetwear has evolved into a fascinating phenomenon. What was once considered disposable and obnoxious has become a billion-dollar industry, thanks to brands like Supreme. This style emerged from California surf culture in the 1960s but...

Streetwear has evolved into a fascinating phenomenon. What was once considered disposable and obnoxious has become a billion-dollar industry, thanks to brands like Supreme. This style emerged from California surf culture in the 1960s but gained mainstream popularity in the 1990s with the rise of skateboarding and hip-hop.

Now, the generation that grew up with streetwear is entering adulthood, and their love for hoodies and graphic tees hasn't faded. With dress codes becoming more relaxed, streetwear has adapted to mature tastes as well. Whether you want to refine your casual wardrobe or experiment with a new style, here are six ways to wear streetwear outfits without looking like you're trying too hard.

The Rules of Streetwear Outfits

Rule One: Luxe Up Your Fabrics

In the past, streetwear clothes were all about durability and comfort, often made from denim and heavy cotton. However, modern streetwear has moved beyond the skatepark. Designers have elevated staples like hoodies, cargo trousers, and trainers, turning them into garments that exude style and sophistication.

Rule Two: Don't Be a Hype Beast

While hype is crucial in youth culture, age brings a change in perspective. Older streetwear enthusiasts should focus on what they genuinely like and what suits them. Instead of chasing after brands that attract teenagers, explore innovative labels that maintain a lower profile. Brands like Pop Trading Company and Acne Studios offer urban-inspired pieces with subtler branding.

Rule Three: Start From The Bottom

When building a streetwear outfit, it's essential to pay attention to your choice of bottoms. Straight-leg shapes have replaced slim fits, providing more comfort and movement. Opt for well-fitting jeans or cargo pants, and balance out the relaxed silhouette with a cropped jacket or a fitted top.

Rule Four: Think Loose, Not Baggy

While baggy clothes may suit teenagers, they can overwhelm adults. Streetwear is a lifestyle that resonates with people from all walks of life, so find a relaxed fit that complements your body shape. For example, pair loose joggers with a more fitted top or try straight-leg trousers with an oversized bomber jacket.

Rule Five: Bring The Streets To Work

Streetwear has infiltrated every aspect of menswear, making it easier than ever to incorporate this style into your work wardrobe. Start with simple additions like a hoodie layered under a bomber jacket or a pair of sneakers worn with a relaxed suit or chinos. These small touches can elevate your office attire with a contemporary edge.

Rule Six: Keep It Simple(ish)

The beauty of streetwear lies in its mix-and-match nature. Instead of meticulously planning your outfit, embrace the spontaneity of this style. Combine pieces from different brands and cultures that reflect your personal preferences and interests.

Now that we've covered the rules, let's explore some of the best streetwear outfits for men that will surely turn heads.

Best Streetwear Outfits for Men


Joggers are the epitome of streetwear comfort and style. From sweatpants material to denim or khaki, joggers come in various forms. Pair them with hoodies, bomber jackets, or even a casual blazer and a white t-shirt. Be sure to choose joggers with a tapered ankle and a drawstring waist for a fashionable streetwear look.

Reiss streetwear outfits Image Credit: Reiss

Cargo Pants

Don't underestimate the versatility of cargo pants in streetwear outfits. These practical trousers are a staple of the streetwear culture. Match them with a polo shirt, a dad cap, and a bomber jacket for a classic streetwear look. Alternatively, pair them with a bold logo tee and an oversized hoodie for a more edgy style.

orSlow streetwear outfits Image Credit: orSlow

Big Hoodies

Oversized hoodies are at the heart of streetwear fashion. Opt for loose-fitting sweatshirts that still flatter your figure. Create a contrast in your outfit by pairing a loose sweatshirt with skinny jeans or straight-leg trousers. Complete the look with sneakers or chunky boots for a touch of thoughtfulness.

Adidas streetwear hoodie Image Credit: Adidas

Classic Sneakers

No streetwear collection is complete without a pair of classic sneakers. Converse All-Stars, Nike Cortez, Old Skool Vans, and Jordans are timeless choices that add a '90s vibe to any outfit. From dressing down a suit to making your streetwear stand out, classic sneakers are a must-have.

Vans streetwear outfits Image Credit: Vans

Denim Galore

Denim is a versatile and timeless fabric that has found its place in streetwear fashion. Embrace the Canadian tuxedo look by pairing a denim jacket with jeans in a matching wash. For a trendy twist, experiment with different colored denim, like a black jean jacket with light-washed jeans. With denim, you'll never go out of style.

Levi's denim Image Credit: Levi's


Camo is back and better than ever in the world of streetwear. Rock a pair of looser-fitting camo pants with solid neutrals like black, tan, olive, or white to create a bold yet balanced look. You can also experiment with camo jackets to add an extra layer of style to your outfit.

Stussy streetwear outfits Image Credit: Stussy

Track Suits

Track suits have been a streetwear staple for decades, offering comfort and style in one package. Whether you opt for a full matching sweatsuit or mix and match different pieces, track suits make it effortless to embrace streetwear. Pair them with classic sneakers, and you're ready to hit the streets.

Sergio Tacchini streetwear outfits Image Credit: Sergio Tacchini

Polo with Jeans

The combination of a solid-colored polo shirt and jeans is a timeless look in streetwear fashion. To elevate this outfit, choose classic sneakers that complement or contrast the polo. Layer with a denim jacket, bomber, or casual blazer that showcases the polo. Add a hat, chains, and a watch to complete the streetwear vibe.

Stussy streetwear outfits Image Credit: Stussy

These streetwear outfit inspirations will help you take your style to the next level while maintaining a mature and fashionable look. Embrace the comfort and versatility of streetwear and make it your own. Remember, streetwear is about expressing your personal style and reflecting your unique interests. So, go ahead and experiment with different pieces to create a look that truly represents you.