Up Your Streetwear Game: 5 Tips for Styling Hype-Worthy Street Outfits

Michael DeMoya

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By PAGE Editor

Streetwear fashion trends were popularized in the 1990s. It drew inspiration from hip-hop and skater culture and involves casual comfortable clothes. Recently, streetwear is making a comeback as more brands and designers are offering street-style pieces to appeal to modern tastes.

While streetwear outfits can be worn by all genders, they are often linked to menswear pieces like leather bomber jackets and workwear. The trend is also traditionally associated with physically fit men who have bigger upper bodies and slimmer lower bodies.

Michael DeMoya

A streetwear look can encompass a wide variety of clothing types and aesthetics. What defines this style, though, is the ability to appear put-together while staying casual and comfortable at the same time. Additionally, outfits from this era were always original yet low-key and relaxed.

With all these different considerations, it can be challenging to come up with a trendy street-style outfit. Whether you’re trying this fashion trend for the first time or are hoping to upgrade your look by giving it a shot, here are some tips for hype-worthy street outfits.

Invest in a Great Pair of Sneakers

The base of many streetwear outfits is a trusty set of sneakers. Indeed, these accessories can create a big impact on your overall style and can make or break your whole outfit.

While some go-to sources of this footwear are popular athletic brands, many high-end designers now have streetwear-ready sneakers available for purchase as well. These offerings include classic white sneakers that pair well with any outfit, high-cut ones that exude an urban feel, and retro-style sneakers that pay homage to the decade that brought streetwear into fashion.

Sneakers come in many styles, and a lot of the trendiest ones are often worn by guys in basketball courts and skate parks. Interesting enough, in the past, skateboard athletes preferred sneakers with thinner soles to provide better board feel and control. But more recently, sneakers with elevated soles are considered more stylish and the way to go when creating streetwear looks.

Make Sure You Have the Right Socks

Whenever you’re wearing sneakers, always make sure you have the right pair of socks on, too. It will not only help you exude a streetwear vibe, but also keep your feet dry and comfortable.

For sneakers, the best type of socks to go for is crew socks, as they settle mid-calf and suit a variety of sneakers styles. When buying crew socks, be mindful of the size they come in and make sure to get an exact fit. That way, you won’t risk the socks riding down your calf throughout the day.  

Go for Loose-Fitting Clothing

One of the key factors of streetwear is comfortable clothing. The pieces must not feel restrictive or hug the body too tightly. Instead, your garments must be loose enough to let you move freely without making you appear as if you're being engulfed by your clothes.

You can achieve a stylish streetwear outfit by picking the right shirts and outerwear. Select from popular pieces associated with the trend, including sweatshirts, hoodies, and loose graphic t-shirts. Remember to choose shirts that are a size larger for a relaxed fit.

This strategy is also helpful when picking outerwear you can layer over your shirts. Some top picks that can enhance your outfit include bombers, puffer jackets, and parkas. They add just the right amount of bulk while also making it appear like your body has ample room to move around. These pieces are also more streetwear-appropriate when compared to pieces like tailored pea coats and blazers, which feature more distinguished silhouettes more closely associated with formalwear.

Play with Various Colors

Streetwear lets you try clothes in various colors. While neutral hues like black, white, gray, and blue are staples, you can still have fun with unconventional colors. For example, you can play with bright and vibrant neon hues to channel early 90s fashion. If you want to experiment with your color palettes, start with subdued muted pastels. Then, you can expand your color choices from there.

When trying on color combinations, remember to pick pieces that complement each other. As a general guide, match a bold-colored piece with something neutral or laid-back. For example, if you’re wearing a vibrant graphic shirt, pair it with blue jeans or dark chinos to balance things out.

Experiment with Proportions

Rather than prioritizing a balanced silhouette based on your body type, streetwear allows you to play with proportions to create a fashionable outfit. While this fashion trend is influenced by the baggy clothes popularized by 1990s hip-hop culture, the latest streetwear style has since been refined. Now, straight-leg and slim pants are considered stylish streetwear pieces that can be paired with loose shirts, sweatshirts, and oversized jackets.

If you’re not familiar with them, straight-leg pants are described as trousers that have a similar width from the knee to the leg opening. On the other hand, slim-fit pants have tapered leg designs but do not cling to the ankle like skinny pants often do. Also, both these styles of pants are more comfortable to wear and offer better movement than their more body-hugging counterparts. In terms of pants color, white, black, and blue jeans are popular choices.

Streetwear is a trendy and comfortable style that suits many individuals, and you can make it work for you, too. Although it involves casual pieces like sneakers, hoodies, and jeans, streetwear outfits can make you look put together and stylish—as long as you know what you’re doing. Above all else, when creating a streetwear outfit, remember to inject your character into your ensembles. In most cases, choosing elements that express your unique personality is the best way to complete your overall look.

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