Vintage streetwear has been one of the hottest trends for a while now and probably won’t be going anywhere. It’s a style that breaks all the rules and otherwise couldn’t care less about what you think. If you want to give your wardrobe a healthy dose of angst, these streetwear looks will make you feel like a true 90s kid.
Whether you’re a fan of 90s basketball or not, these white high-topped Nike sneakers are essential to streetwear. The light blue accents complement the denim to make them look more cohesive. Just make sure to keep them looking clean at all times.
Don’t feel like dealing with people? Streetwear can let your clothes do the talking. Graphic tees like these give off the perfect amount of attitude for making a statement. Pair with a pair of vintage sunglasses and hide underneath a bucket hat and no one will see the number of times you roll your eyes.
A vintage basketball tee makes for perfect streetwear, especially if you wear it ironically. You don’t have to be a fan of basketball to rock this Chicago Bulls shirt. Apparently, they did pretty well as a team in the 90s, so what better way to capture it and show off your hometown pride.
Faded black tee
When it comes to vintage streetwear, you want your clothes to look worn in. A black tee makes for a great basic that you can throw on any wardrobe and instantly make it look vintage. The more oversized and faded the better. The chain necklace and any other jewelry are always welcome accessories.
Converse are the shoes that look good in any decade. High tops especially really bring out the frays in your jeans. Pro tip: shorten the length of your jeans to really make the high tops and white tube socks are seen. You can choose to keep it simple with this white top or oversized tee. Either way, your style will truly pop.
On the opposite side, these Doc Marten boots add in an industrial style that encapsulates the edginess of the 90s. These platform boots give you extra height as you walk down the street and add in extra style with the zipper feature. These boots are a must-have to add in a goth element to streetwear along with the black turtleneck, gray patterned trousers, and studded belt.
Oversized printed tees
We mean it when we say the oversized the better. Oversized tees bring out an exaggerated silhouette that rides the fine line of wearing a shirt and a dress. An oversized shirt makes bottoms optional, but faded denim shorts are the best way to go. There’s also something about sports-related shirts that define vintage streetwear. This NASCAR shirt is the perfect example of clothing that was popular in the 90s and brought back to life.
What better way to show you don’t care than with distressed denim. Despite what your mom might think, holes in your jeans are absolutely welcome in vintage streetwear. Some jeans may be sold with holes already in them, but cutting them yourself or waiting for holes to appear on their own keeps it authentic. This look works best with an athletic or loose-fitting light wash jeans (otherwise known as boyfriend jeans) as part of the streetwear look.
An alternative to jeans for bottoms are these cargo pants. Utilitarian by design, these pants are made to show how much you mean business with plenty of pockets that give these pants many points of interest. Low-hanging chains and chunky belts are welcome accessories for this look. The lower they hang, the better.
The best part about streetwear is that any piece can be a statement piece. Camo as a pattern is pretty underutilized in fashion but gives a vintage flair to streetwear looks. Keep it simple with a cropped black T-shirt or go all out with this pattern. Contrasting the camo with an athletic high-top shoe is sure to bring out the streetwear vibe.
Speaking of camo, you will not be limited to the typical camo pattern. A pop of color like these orange camo pants will make sure you won’t go unnoticed walking down the street. The skater look really took off in the 90s and so have classic black Vans which haven’t really gone anywhere since then. This combo looks good in any decade. You just might want to take up skating as a main form of transportation.
Neon is not just reserved for the 80s. In fact, neon was taken to new heights through streetwear in the 90s. Since overalls have made a comeback in recent years, why not make them neon with a dangling chain and belt? While oversized is typically the norm in streetwear, a more fitted look makes the look more futuristic if that’s the vibe you’re looking for. Paired with a fitted or loose white long-sleeved shirt perfectly blends the past with the present.
For a more vintage look, denim overalls work just as well. This particular look makes the accents work as the pink and white appear throughout. The white Fila sneakers offer a sense of exaggeration which more or less is what streetwear is all about. For more street cred, keep one strap of the overalls fastened and the fit loose and comfortable.
Would this list even be complete without a windbreaker? These lightweight jackets offer bright spots of color to your outfit all at one time. The lightness of the windbreaker also makes sure they can be worn at any time of the year keeping you cool literally and figuratively. This particular windbreaker offers more muted tones of color that work well with black track pants, but feel free to get crazy with the colors.
Feeling a little risque? Wearing high-wasted fishnets underneath distressed denim makes for the ultimate power couple when it comes to vintage streetwear. Throw on a cropped Thrasher T-shirt and you will be the literal definition of 90s streetwear. This outfit is perfect for skating a half-pipe or dancing your heart out at a music festival.