53 Best Streetwear Outfits for Men & Women in 2020

You will probably be surprised to find out that streetwear, just like hip hop fashion or overalls, actually has a history behind it. Ever heard of Shawn Stussy? He’s credited as being the creator of the streetwear movement in Los Angeles, designing surfboards and t-shirts with his own logo.

Streetwear originated as a comfortable, casual style often worn by skaters and surfers, but it was later picked up by high-end luxury fashion labels and was propelled into the mainstream. It’s considered fashion for everyday people who want to express themselves, rather than wear what is considered super trendy at the time.

 

Streetwear Outfits For Men

1. Edgy Streetwear Outfits

Streetwear was born out of a desire to get away from the mass produced clothing seen on stores across America, and the edgy style is a product of that desire. Gone are the clothing pieces you might see all your friends wearing where everyone seems to resemble each other as if there is some kind of strict uniform policy. Edgy streetwear asks to be looked at as unique and having more personality than the average mall shopper.

Rather than your average denim jeans, try a pair that is tighter fitting, perhaps with some rips to really stand out from the crowd. In the time since streetwear has become more mainstream, many high end designers have taken on the task of recreating the look to be more fashionable and runway appropriate.

A short sleeve polo screams style and sophistication but paired with jeans it remains a streetwear uniform. Paired with designer sneakers, the whole outfit pulled together creates a symbiotic relationship between high fashion and casual, and comfy; exactly what streetwear has become today.

Though, true streetwear is more about comfortable clothing, loose styles, and simple colors; it’s your basic weekend look when you want to lounge on the couch but still look stylish. Pair loose fitting chinos with a cozy sweater but keep the outfit chic with a black pair of boots.

 

2. Hiphop Streetwear Outfit

Taking it back to hip hop, or one of the origins of the current streetwear movement, you can easily wear something inspired by the style but without being so ostentatious. While much of the hip hop look in the 80s and 90s was all about ‘bling,’ flashy accessories, and expensive tracksuits, you don’t have to go so far with streetwear. 

To wear a hip hop inspired streetwear outfit, think tighter jeans in blue or black, but with a bigger, looser top. A simple white t-shirt is perfect for styling this look as it’s comfortable and not too showy, but can easily be paired with any personality. You can throw on a denim button down shirt over it, or even a black leather jacket. 

Much of the current hip hop streetwear is about oversize pieces, like longer t-shirt and long zip up sweaters. If you really want to be inspired by the hip hop artists of the 90s and 2000s, you can’t lose with a camo jacket. Camo was hugely popular among hip hop artists like Tupac, but also became super popular with the youth based on how inexpensive and accessible it was. 

Of course, if you’re a simple guy who likes to keep his outfit easy, a plain white shirt with jeans is an easy way to go, and can be hip hop inspired with some sports sneakers or flashy accessories.

 

3. Urban Streetwear Outfits

The urban guy who likes streetwear, but in a more sophisticated setting; think tailored shirts with heavy jackets like leather. Comfortable jeans, that are also matched with a chic pair of shoes. Streetwear doesn’t always have to be super casual, or loose fitting. The urban streetwear look has taken things up a notch with accessible style that has just a little something extra like a flashy accessory or expensive pair of shoes. 

A white leather jacket is super chic, and can be dressed down with a loose fitting button down underneath, and ripped jeans. A white and beige pair of laced up boots show a super fashionable side of someone who is trying to be casual but wants to be noticed at the same time. An all black outfit can easily be taken down a notch with a pair of streetwear inspired Vans skater sneakers. 

To keep a casual look fancy enough to be urban, try an outfit with every piece in a similar color family. A soft, beige winter jacket, simple white t-shirt, beige pants and white sneakers make a super easy going outfit, but the chic colors lend it an air of business casual. 

If you’re wanting to go super formal but keep it urban and casual, pair sophisticated trousers and tops with multiple layers.

 

4. Vintage Streetstyle Outfits

Vintage streetstyle is like any other streetwear, but what takes it back decades is the pattern and textures you choose in your outfit. A pair of plaid trousers and a leather jacket are very 90s but super wide black sneakers bring back a casual vibe.

Of course, nothing says 90s like denim on denim, and fortunately that is the texture of the streetwear movement. Comfortable jeans, paired with a denim shirt scream the Midwest, but Converse sneakers bring the outfit right back to New York or L.A. A suede jacket thrown over contributes an extra layer to an otherwise overly simple outfit.

Of course, denim jeans paired with a denim jacket are also super 90s but you can make it look more chic with a pair of suede Chelsea boots. You can easily find denim jackets and other vintage pieces at a thrift store; buy just one item and accessorize your outfit around it. If you’ve got a super trendy denim, button down shirt, you can play around with the rest of the outfit a bit more, but the eye will be drawn to your chosen attention grabber from the thrift store.

Vintage doesn’t always have to mean super casual either; a pair of patterned trousers with a brown leather belt and matching loafers screams Italian Riviera but a simple white t-shirt keeps the outfit casual.

 

Streetwear Outfits For Women

1. Chic Streetwear Outfits

Despite the roots of streetwear being super casual and comfortable, the style has taken on many distinct sub-genres, with many young people wearing a more high-end version. Digital fashion editor for High Snobiety, Alec Leach, told Who What Wear, “No one’s going out on a Friday wearing a suit.It’s not a case of the culture getting so huge. It’s that it’s become the logical way of dressing.”

If you choose to wear a chic streetwear outfit, you’ll want to find a balance between high fashion and casual by wearing clean colors with tailored silhouettes, yet not going overboard on accessories or things that call attention. Avoid items that look tight or uncomfortable, streetwear is all about looking like you aren’t trying too hard.

You can wear a chic winter jacket but keep the rest of the outfit super comfy with a simple, oversize sweater. Streetwear is all about loose fabrics. If it’s not something you would hang out on your couch in, then it’s too fancy.

If you want to wear a fancier item, like high heels, make sure you pair them with other super casual items, like a loose fitting pair of jeans. If your whole outfit is super chic, like a pant suit, make sure you wear it one size bigger so it fits you loosely and pair it with other casual items like a t-shirt.

 

2. Edgy Streetwear Outfits

Edgy streetwear takes a super casual outfit, and accessorizes it with more attention grabbing pieces like leather fabrics and darker colors. If you stick with a completely casual streetwear look, like a simple white t-shirt and loose fitting jeans, throw on an edgy piece like a black leather jacket over. You can also add a pair of skater sneakers in noticeable colors to draw the eye.

For a more chic, edgy streetwear look, wear simple minimalist colors but with noticeable fabrics like a fur jacket, or a noticeable accessory like a super tiny purse. If you want to stick with a streetwear look that draws on the athleisure movement, throw on a comfy pair of sweatpants with bright sport sneakers. To give the outfit some edge, finish off the look with an oversize jacket in a chic pattern.

The streetwear look also had origins in the hip hop fashion movement, so you can give your outfit some edge by drawing inspiration from artists like LL Cool J. Try accessorizing with a bucket hat, or a fanny pack around your chest. When going for an edgy look, you’ll want it to look super comfy and casual, but resemble something a model would wear down the runway.

 

3. Hip Hop Streetwear Outfits

While hip hop fashion and the punk movement had a huge influence on streetwear, it really started out as a mostly urban look popularized by skaters and surfers. Despite high fashion labels jumping on the bandwagon, pushing the flashier streetwear look that was trendy in the 90s, it has and will always be a look for everyday people.

The urban streetwear look draws heavily on the personality and personal style of the person wearing it, but in a casual, easy way. If your look is a bit edgier, wear comfortable fabrics in darker colors, like black, and lots of leather. If you tend to go for a more hip hop style, try edgy pieces like black leather but accessorize with athleisure like sports sneakers and a puff jacket.

If you’re the super casual type, a loose fitting logo t-shirt with mom jeans and a pair of skater sneakers proves highly fashionable. An urban streetwear look doesn’t have to be so sporty or draw on hip hop style though. If you’re a super feminine girl, try a loose fitting pair of jeans with a lot of lighter colors, like a sea foam green sweater. Accessorize with sporty pieces like Nike socks and a designer bag like Louis Vuitton.

 

4. Urban Streetwear Outfits

 

 

5. Vintage Streetstyle Outfits

Vintage streetstyle is all about unique patterns, showing off your personality, and taking inspiration from the 80s or 90s while still remaining comfortable. While many brands make clothing that just appears vintage, it’s easy enough to find a concert t-shirt or a cool pair of plaid leggings at a thrift store.

Vintage streetstyle outfits are one of the easiest looks to pull off as there are so many options. An oversize trench coat is the perfect statement piece; think George Costanza on Seinfeld, but with trendier accessories. Pair this with a simple pair of straight leg jeans and a t-shirt. If you want to mix in a little sophistication, pair your outfit with a designer bag.

For a 90s streetstyle look, try the pattern of the decade; plaid leggings paired with Converse sneakers. Keep the outfit super casual and comfy though, with an oversize sweater. Vintage streetstyle doesn’t have to be fully casual; try a leopard print dress, or a tailored blazer to lend some sophistication to such an urban look.

While most vintage streetstyle seems to be inspired by the 90s, the 80s was the decade that started it all, so why not pay homage to that with an edgy look. Try a black leather coat with lots of metal accessories.