How To Dress Streetwear (The Right Way)

How To Dress Streetwear (The Right Way)


Although some streetwear brands cater for both genders or are unisex, streetwear fashion is predominantly still linked to menswear. Other characteristics of streetwear style include contemporary art, logos, and of course comfort.

Perhaps most importantly, streetwear fashion is not a uniform. The streetwear scene developed from DIY and counter culture. You can take the bits that speak to you, and ditch anything that does not appeal to you.

In this blog, we will offer up a few suggestions on how you can use streetwear fashion to create your own style.

Key Pieces of Streetwear Style

If you're going to style a streetwear outfit, first you need to know a few of the key streetwear pieces you should have in your wardrobe.


Apart from sneakers, hoodies are perhaps the most worn streetwear staple.

A streetwear hoodie may be zipped or pulled on. It could have a large logo on the back or a big front pouch for convenience. Perhaps for throwing on to head to the gym or out for a run, they can be outerwear or provide an extra layer under a puffer coat or bomber jacket. We offer a huge range of hoodies in shades from classic black and off-white, to Coral, Cobalt, and Pastel Lilac.

Sweatshirts & Sweatpants

In a similar vein, sweatshirts and sweatpants form the basis for many a streetwear outfit. Most sweatshirts are cotton and crew neck. They too, may sport large logos or be left clean and simple.

The slightly oversized fit Owners Club Sweater - Ash Grey is a classic piece in a wearable shade. Super soft and comfortable, it's also easy to pair with jeans or cargo trousers.

Alternatively, style with matching sweatpants, a contrasting tee and our Harrier Vintage White sneakers.

Cargo Pants

One of the most recognisable elements of the streetwear fashion style is the cargo pant. Our Military Pant V2 in Olive is a contemporary, lightweight take on the look. You still have all the key elements of a cargo pant, including the abundance of cargo pockets. They're just in a new slimmer silhouette to keep you looking fresh and modern. Wear with graphic tees or an everyday T-Shirt in Flat White.


Whether baggy or skinny, jeans are a big part of streetwear fashion. Shredded and distressed jeans, such as our Essential Denim - Paint Black another style that should be in your wardrobe.


T-shirts can be used to make a statement or to create an effortless streetwear outfit. The Raglan Blanks tee lends itself to the latter. Available with long or short sleeves, this versatile piece comes in black or white with contrasting shoulder panels in a heavyweight cotton jersey. Slightly oversized, the ribbed hem and cuffs offer a comfort fit.


Sneakers are an integral part of the streetwear aesthetic. Your battered old kicks won't do. Instead, invest in some classic-style footwear that will complement any streetwear outfit.

Our Apex collection features premium sneakers in a mix of tumbled and flat leather. The zig-zag stitching, suede uppers, and leather piping are reminiscent of vintage basketball elements. You can also switch up the laces to change your look, with Vintage White and Black both included.

Varsity Jackets

Harking back to the 1950s retro American 'Letterman's Jackets' the Varsity Jacket continues to be popular in streetwear in 2022.

Lettering in a particular sport meant you were a high-calibre athlete. Naturally, these jackets are also associated with youth. This mix appeals to the streetwear movement. The RPRSNT Varsity Jacket is a black boxy fit jacket with faux matt leather sleeves. The RPRSNT logo is emblazoned across the back of the shoulders, with the R and the big cat motifs on the chest. Winged women adorn the lower sleeves.

This kind of jacket makes a statement so keep the rest of the outfit simple with dark jeans and bright white sneakers.

Not your style? Don't worry, streetwear offers up a wide variety of jacket shapes and styles, from bomber jackets to puffer jackets and many styles in between.

Shearling Jackets

Fashion is cyclical, but Shearling Jackets never really go out of style. Our Shearling Jacket is made from 100% sheepskin with a sheep fur lining in an oversized fit. The funnel collar provides extra warmth, while details include front zip pockets and leather tape seams.

Available in black or grey, this is a true investment piece that should elevate any jeans and t-shirt combination.

Of course, there are many different kinds of streetwear outfits that can be created from key pieces such as these. So, how do you know if you're getting it right?

Dress for the Occasion

You may have heard the phrase a 'Canadian Tuxedo' when referring to double denim outfits. The idea is, of course, that Canadians wear so much denim that they will even wear it as formal wear.

The streetwear equivalent may well be cargo pants, graphic tees, and expensive sneakers.

However, be sure to keep in mind where you are going and who will be there. For example, our As Good As Dead Hoodie looks great under most circumstances, but would be wildly inappropriate for a wedding reception, let alone a funeral!

Instead, go for Tailored Pants and black shoes, such as the Alpha Low Triple Black and a crisply ironed shirt.

Pay Attention to the Weather

Simply put, it's hard to look cool if you're freezing. Likewise sweating buckets (outside of a strenuous workout) is not a good look.

Look for breathable fabrics, and water-resistant technology to help you complete the assignment without having to battle the elements. We've got plenty of winter fits and all-weather items to keep you on track.

Your Streetwear Style

What makes streetwear fashion so appealing is that it's not restrictive. You can wear streetwear brands however you choose to. Streetwear clothing encompasses many brands, styles and of course, products. You can swear loyalty to one particular streetwear brand, or mix and match. If there is a prominent logo though, it's best to stick to one brand per streetwear outfit.

Streetwear fashion can be dressed up or down, depending on how you style the individual pieces. The Nivea shirt looks like a classic style black shirt. However, it's actually an overshirt, designed to be worn multiple ways. Wear over a tonal hoodie for a laid back layered look, or to reveal a brand logo. Alternatively, a black t-shirt is all the base you need to wear it closed for a smarter look.

Wearing streetwear the right way simply means developing your own streetwear style. Streetwear takes inspiration from a variety of pop cultures and fashion movements, and you can do the same.

If you want to start building your won streetwear outfit, take a look around our shop.

With free shipping UK-wide and a variety of discounts elsewhere on the site, there's never been a better time to upgrade your streetwear. This is a great time to shop at Represent.

How Streetwear Became a Fashion Style

Although it's thought to have its roots in the post-War era, it was skaters and surfers, and the emergence of hip hop, that brought streetwear into popular culture.

In contrast to the sometimes stiff and starched look of a suit and tailoring, streetwear combined form and function with freedom of expression. It not only looked great but, crucially, it allowed the wearer to move. These are still the same principles that the best streetwear clothing follows today.

And streetwear style is continuously evolving, along with streetwear culture. Hip hop fashion has continued to influence streetwear labels and vice versa. However, you can now find streetwear haute couture. Now, rare, high-fashion items are collected by 'hypebeasts' who will pay megabucks for a limited edition baseball cap or sneakers.

High-fashion brand Louis Vuitton is well known for collaborations, including 2017's collab with Supreme. At the time of writing, the Louis Vuitton x Nike Air Force 1 by Virgil Abloh Sneaker is selling at $90,000 USD. With further collaborations expected, and other haute couture designers following suit, the high fashion phase of streetwear style shows no signs of winding down anytime soon.

In the meantime, hip hop culture and counter-culture will keep menswear looking fresh and feeling personal.