4 Tips for Styling Men’s Streetwear – LIFESTYLE BY PS icon

4 Tips for Styling Men’s Streetwear

Men’s fashion is always changing, but one of the most prevailing fashion trends in the last decade has been men’s streetwear. To the men who have never browsed Reddit’s r/Streetwear or scoured streetwear hashtags on Instagram, here’s how you can start styling it into your daily wardrobe.

What is streetwear?

First, if you’re uninitiated with the culture, you might be asking yourself, “What is streetwear?”

Men’s streetwear is, simply put, fashionable men’s clothing that is based around comfort and the appearance of being casual. It’s rooted in the artistic sense of old skate and surf culture, as well as trends that have emerged from the world of graffiti and hip-hop. It’s the mix of Supreme accessories, Thrasher t-shirts, v-necks and much more.

4 Tips for Styling Men’s Streetwear

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Streetwear tends to focus on the way in which an outfit is tied together, which you’ll sometimes see posted with the #ootd hashtag (standing for “outfit of the day”). Outfits focus on shirts, hoodies, jackets, hats, sunglasses, pants and (most of all) sneakers.

It’s the industry of cool, not just in the presentation of their clothing but for their overall demeanor of “cool.”

  • Shoes are king.

As mentioned, streetwear sneakers are the pinnacle of streetwear fashion. Shoes will make just about any outfit, as they’re often treated as the main attraction – alongside shirts.

Common streetwear etiquette is to have multiple shoes you can pick from on a daily basis, all of which you can cycle through. Most of all, you’ll want to match the rest of your outfit to the shoes you’re wearing. In the misquoted words of The Big Lebowski, “They really tie your outfit together.”

4 Tips for Styling Men’s Streetwear 


  • Use patterns, monochrome and more.

Besides being built around shoes, most streetwear clothing is focused on patterns, colors and how clothes pair together. The most common form of streetwear fashion includes monochrome outfits.  For instance, this can mean a white pair of shoes with white joggers, a white crew neck tee covered by a large white hoodie and white-framed sunglasses to tie it all together. Or you could do the same, just switching out all the clothing colors with black.

If you don’t want to go neutral and monochrome, you can instead go clashing and neon. Think of someone like Oliver Tree, whose extravagant style and personality are captured in his early-90s outfits. In other iterations, it captures the vibe of early skate and graffiti culture, which is the peak vibe of streetwear.

Similarly, you can instead opt for clothing that prides itself on the use of wild patterns, whether they’re clashing with one another or the patterns remain the same across all clothing pieces. If you’ve ever wanted to step out of the house in full zebra-print clothes, now is your time to shine.

  • Comfort goes a long way.

Another thing to keep in mind is that streetwear prides itself on comfort and relaxation. Most streetwear clothing you see is large and baggy, meant to hang off the skin for ultimate comfort. Think of someone like Billie Eilish when she first hit it big: the massive chains, huge hoodies, gigantic pants and wild jewelry.

There’s an allure to it; one that can be summed up as if you just got off the couch – think of a lot of Yeezy clothing and shoes, which are based around monochromatic colors and appear to be as orthopedic as possible.

Clothes can vary, whether you’re wearing JNCO jeans, a long-sleeve crew neck covered by a sweatshirt that’s three times larger than your shirt and a bucket hat or something a little more uptown. Whatever outfits you decide to explore, you should work to make them look as casual and relaxed as possible, whether that’s you going out for a day at your local skatepark or you just crawled out from under a hypebeast blanket fort.

4 Tips for Styling Men’s Streetwear

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  • Go for an athlete’s touch.

But not all streetwear is baggy comfort. For some people, streetwear can involve the athlete’s touch. This doesn’t mean wearing tights like you just came from the gym or a serious track workout. But it can involve high-end athletic shoes, form-fitting joggers and a retro-styled windbreaker with sunglasses out of the 80s.

These looks can be taken far and wide, depending on what feel you’re going for. You can even begin to pair it with a relaxed look too. This could involve wearing a pair of form-fitting joggers with an exceptionally baggy sweatshirt. Or you could look like you’re coming right off the mountain slopes, while transported from the 90s to now. That can include warm, insulated clothes that have the bright features of decades long past.

Where to Begin?

Still looking to get into streetwear but don’t know where to start? Consider going to some local shops and checking out what they have in stock, seeing if it either fits the streetwear mold or your personal style.

If you’re still not sure where to start, you can begin by checking out forums like Reddit’s r/Streetwear. Not only can you gain advice from people regarding your fashion sense and progress, but you can get to better know the essentials of streetwear clothing and accessories.

Lastly, remember that layering is your friend when it comes to streetwear. It’s a simple way to start building out your outfits, getting yourself into a confident mindset.

4 Tips for Styling Men’s Streetwear