How To Wear Streetwear Without Trying Too Hard

Whether you’re going in for a job interview, taking someone on a date, or heading out for vacation, here’s how to wear streetwear in different scenarios.

September 12, 2023
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Creative Job Interview

 
Shirt by Heron Preston; Pants by Willy Chavarria; Footwear by Adidas.

Tip: Try a New Silhouette by Adjusting Your Waistline

When coming in for a creative job interview, it's important to keep it fashionable but not too casual. You shouldn't wear a Supreme hoodie, Fear of God sweatpants, and Nike Dunks. While that would usually be a valid outfit for the street, you still need to keep it professional and scale up from your everyday looks. This doesn't mean you should force yourself to wear a bland suit from Men's Wearhouse. It's important to strike a balance, especially if you're being interviewed for a job where taste matters. As shown in the example above, a button-shirt with a chill logo hit from a designer like Heron Preston shows you're serious about the job but also tapped into contemporary style. Leave the cargos at home and instead go for trousers that look formal but are defined by a unique silhouette like these "Caballero Pants" by Willy Chavarria with super wide leg openings. Lastly, when it comes to footwear, sneakers are fine as long as they're calm. Leave the "Chunky Dunky" Nikes at home and instead go for a subtle leather sneaker like Adidas Sambas.

Date Night

 
Jacket by Stüssy; Cargo Pants by R13; Footwear by Stüssy x Nike.

Tip: Pair Patterns With a Plain Top or Bottom

There's two ways to dress for a date. One is to just come wearing whatever you have on and hope the stars to align. While that works sometimes, a better approach is to make sure you put together an outfit that your date will remember. The easiest way to do that is to wear something with a distinct pattern or print. Take this yet to be released canvas jacket from Stüssy as an example, which is further accentuated by a bold tie-dyed layered jersey by Who Decides War. However, what's key when wearing a bold pattern or print is to pair it with a plain top or bottom. As shown in our video, from the waist down, our model didn't get too crazy and Mateo styled him in a pair of R13 cargo pants and all-black Stüssy x Nike Air Penny 2s.

Vacation

 
Sunglasses by Bonnie Clyde; Hoodie by Awake NY; Denim by Who Decides War; Footwear by Birkenstock.

Tip: Wear Logos Mindfully by Breaking Them up With Negative Space

Anyone who's deeply invested in streetwear knows that vacations are one of the best, but hardest, scenarios to approach when putting together an outfit. What's key when packing those bags for your next trip is prioritizing comfort without sacrificing style. And although plenty of tourists are fine wearing sweatpants and a T-shirt from a souvenir shop, some of us need to put together a nice outfit or two while traveling. Since streetwear is rooted in casual basics, vacations can provide ample opportunity to wear chill pieces that also showcase your personality. For example, pieces like a flashy zip-up Awake NY hoodie, Bonnie Clyde sunglasses, Birkenstock Kyotos, and a statement-making pair of Who Decides War jeans can be worn both on and off the plane. However, when putting together these fits, make sure you're mindful of how the logos sit together. It's key to break them up with plenty of space so you don't look like a walking billboard.

Credits

Photographer: Suresh Gordon

Stylist: Katherine Mateo

Model: Nile Winchester of Next Management

Wardrobe Assistant: Dasani Mathis

Hair and Makeup: Sareen Bhojwani