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Streetwear Style Guide

Back in the 80s, streetwear was the domain of skateboarders, surfers, and rappers. It used to be an opposition to luxury high-end style. Today, it is a massive fashion phenomenon, represented on runways and red carpets yet comfortable enough to be worn every day. 

Whether you are ready to embrace the street culture or just want to look effortlessly stylish, this guide is for you. With the focus on versatility, some knowledge, and inspiration, you can stand out from the crowd and make your statement. 

What is Streetwear?

Streetwear is a fashion subculture that emerged in the early 80s in California. Los Angeles surfboarders and skaters started to sell screen-printed T-shirts with catchy and statement-making designs. From the South, the style traveled to New York and extended to hip-hop fans. In the 2000s, sneaker culture joined in. These were people focused on collecting expensive and unique sneakers. And in the next decade, when streetwear became a thing among social media influencers, luxury brands got into action. 

Street style today is the mix of various trends: from American rappers to Japanese Harajuku habitues, from bright surfer vibes to huge sneakers of teenage skaters. It offers a perfect blend of athleisure comfort, hypebeasts’ urge, and freedom of expression with a dash of product scarcity. It is equally widespread among celebrities and high school teens, full-time fashionistas and suburban moms. It is ubiquitous and available for any budget. Yet pulling together a unique not boring look can be a challenging task. 

Street style today

Source: The Trend Spotter

Features of Streetwear Style

Although streetwear can be very different, it still has some characteristics that can help you to understand it better. Let’s focus on four of them. 

It must be comfortable.From the very beginning, street style has been activewear. It includes casual basic pieces, functional athleisure staples that are a definition of comfort. Nothing too skinny or tightly fit. Streetwear is made for active movement and lifestyle. For the perfect vibe, go for loose T-shirts and quality denim. 

Unisex silhouettes. People of all genders can wear the same pieces. Not all of them, but in general, a unisex hoodie or a bomber jacket has much more of the streetwear vibe to it than a dress or high heels. Street fashion clothes are usually good at covering curves. Therefore many items look masculine and one uses abundant accessories to add those feminine touches. 

Rare items are valuable.Streetwear brands are known for creating artificial scarcity for their products. Although it may seem like a bad thing, for hypebeasts it is a part of the fun. They go a great length to fetch a limited-edition hoodie or a pair of sneakers available for a short time only. One-in-a-thousand items are the most fashionable. Especially if it is blessed with a trendy logo or was seen on a hype celebrity.

It makes a statement.Art on streetwear T-shirts and hoodies is bold and eye-catching. It is a declaration of your inner world, a joke, a scream, anything but boredom. The best streetwear designers also manage to make fun of classic brands even while doing authorized collaborations. 

Street Style Wardrobe Essentials 

You probably got all the fundamental basics in your closet already. If not and you are going to build a streetwear wardrobe from scratch, we do not recommend starting with a Supreme hoodie or any other expensive piece. Here are five essentials worth the investments. They can be casual low-key yet quality pieces from a mass-market. You can build on them and incorporate more and more crazy elements into your outfits.


They took the most space in a hypebeast’s closet. Sneakers are a staple in the streetwear culture. Their impact on your look can’t be overestimated. Versatility and comfort are of the most importance here. Try to find yourself a pair or two that work with any outfit. Here are a few options that are undying classics. As for the trends, this year, streetwear aficionados are wearing puffy models with raised soles. 

Nike Air Jordan

The undying classic and a huge footwear trend. Arguably the most popular brand out there. Nothing is beating a pair of Air Jordan’s if you want to be noticed. The price is between $100 and $200 depending on the model. We promise you won’t regret it. 

There are a lot of designs with different soles, silhouettes, and colors. Once you find your perfect fit, you’ll never get bored with Nike’s. That is why celebrities love them so much.

Celebrity couples in Air Jordans

Celebrity couples in Air Jordans. Source Fashion Bomb Daily

Vans Old Skool or Sk8 Hi’s

Iconic shoes for everyday looks. They are affordable and versatile, especially if you go for a classic black or white (or black and white) pair. Padded collars are comfortable and side stripes are bold. What else can we desire? You can buy a pair for only $60-70.


These black or white low tops have been around since the 60s and are still relevant. As well as high tops. With both models, you can dress them up or dress them down. The price is about $55 bucks. 


A basic T-shirtin a plain color like black, white or grey is a must. Go for a comfortable fit that is true to size. You can use them as undershirts for layering (more on that later) or as an actual top. Do not save on quality here, you need good cotton to touch your body. Uniqlo, Hanes, and Killion are just a few brands to look at for affordable and quality options. Ten to fifteen dollars would be a good price for one. 

Graphic tees are a whole different level of streetwear. One can go totally crazy here with all the options. Choosing between Supreme, Stussy, BAPE or Obey is tremendous, but we suggest you start with just one brand and then expand your collection. If you are not ready to invest in a brand name, go for a mass market tee with a good design. For a trendy look, choose something with block colors and a retro vibe. Aggressive prints are back in fashion in 2021 as well as the 90s neon.

Aggressive prints are back in fashion

Source: Rebels Market


You can’t call it a streetwear wardrobe without a hoodie or two. A cool laid back top that is both comfortable and stylish will provide the vibe. Although it is often about the label, you can definitely start with a cheaper option if it has a good design. Or with a plain hoodie with a simple text on it. The essential hoodie should match everything in your closet because you’ll be wearing it a lot.

Wondering what brands should you look into? There are tons of it, starting from the most well known and instantly recognizable Off-White or Bathing Ape to more niche, underground or local. The budget is your only limitation here. A piece from a hype brand can cost you up to a thousand dollars, while a Champion hoodie is much more affordable and still the right choice. 


Source: Highsnobiety


First of all, you need a pair of blue denim jeans. The time when streetwear style meant only baggy pants are long past, so you can go for a suiting slim or straight leg fit. Moreover, pants are not a central piece any more (that place is taken by hoodies and sneakers). They will calm down and balance your look. You can never go wrong with Levi’s. They have every possible fit and shade. But the most popular model is Levi’s 511. This style will never die out.

The second pair should be joggers, the most comfortable pants out there. There are numerous types of joggers: chinos or sweatpants, with pockets or without. We suggest starting with black wide pants like these.


As usual, there are tons of options for jackets. But we suggest starting with a regular denim one. It will make a perfectly versatile outer layer of your look. 

Other classic options include flannels, bombers, and parkas. To choose, take close attention to the silhouette you want to create. If you want to go big, a puffer jacket might be the best option. 


Source: Pinterest


You might spot a person in the same hoodie in the city. It is the accessories that make your outfit unique. Some outfit-making essential staples include:

A logo belt. A genuine Off-White might be too much for a beginner, but you can find more affordable options to boost your performance with some signature flair.

Sunglasses. It may be a pair of classic aviators or something completely bold. You choose.

A bag. Or better a backpack.Or an across-the-chest sling. The options are endless, yet an old-fashioned backpack in funky colors is the best one for starters.

The hat. A beanie, bucket hat, or a good old baseball cap. Even though these are not essentials, they can spice up your game and add some flavor.
Gold chains and plated watches are no basics. However, they can be quite an interesting addition to your hardcore hip-hop outfit. 

Do not throw it into the pot altogether. You can choose one accessory and build the whole outfit around it.

How to Create a Stylish Streetwear Outfit

There are two ways: a simple path and a more interesting one. For an easy look, you just pull on your favorite jeans, box logo hoodie, and massive sneakers, and voila, you can snap a picture for an Instagram. However, such an outfit might be a little bit too basic. To up your game you make a little bit more effort. With the solid foundations listed above and some tips, it won’t be a problem. 

Add Layers

Layering is streetwear 101. Not only it is great for chilly days, but it also adds personality and thoughtfulness to your look. There are a whole art and science theory to it, but the rules are as follows: 

From thin to thick.Start with the T-shirt, so that the first layer is the thinnest. While you add more layers, the thickness of the garment should increase. Finish with an oversized coat of a stylish jacket. 

Use pieces of different sizes. Your jacket will feel differently if you wear it on a T-shirt or a hoodie. To make the layering comfortable go for a size-up outwear. 

Use the color theory. It is easy if you use only neutral or basic colors, black and white always go well together. However, if you decide to add more shades, make sure they match each other. Choose the central piece and make sure other items complement it. 

Make sure every layer is visible. Otherwise, what’s the point? 

layering is streetwear

Source: Reddit

One logo at a time

This will just make your life easier because combining logos is hard. Moreover, brand loyalty is a thing in streetwear culture. So keep it simple and mix designer clothes with basic athleisure pieces or workwear. Silent logo style (with no logos at all) is trending now, so if your outfit screams a brand name, try to tone it down a little bit. The key to success is that the components blend seamlessly with one another. 

Play with proportions

Variability of silhouettes is what makes streetwear so interesting. You can go heavy on the top with an oversized hoodie at the bottom with chunky sneakers. Yet we suggest you balance the proportions so that you don’t look like a bear. A belt can be a helpful accessory to achieve a nice silhouette. However, if you feel particularly adventurous, this is just another rule to break. 

Show the attitude

As Raf Simons once said,  "I don't want to show my clothes, I want to show my attitude". 
Your outfit should be built by your rules, that is what streetwear truly means. This style is rebellious and unexpected. Experiment with combinations, pull things together the way you feel and find your signature vibe. Streetwear is what you make it.