How to Dress Street

How to Dress Street

Dressing street is something many of us do but rarely pull off, so this style guide is here to help solve that. 

Check out the rest of the How To Wear It guides here.

Streetwear is a style that’s had a huge resurgence over the past couple of years and it’s now a look that seems set to stay. Gone are the days of Vicky Pollard-style tracksuits, TN caps and Sovereign Blacks, street is now a premium look, donned by many a stylish man at fashion weeks all over the globe over the past two years or so.

The main component to a street look is the fittings. Keep things to a looser fit and don’t be afraid to try out long line and oversized shapes. So, to show you how to do it properly, I’ve put together a few go-to looks anyone can pull off.


One pretty key part of dressing street is heading to the right brands and brandishing their logos with pride. Go for a relaxed fit in your jeans, a slightly bigger size in your T-shirt under a sweatshirt (allowing some of the tee to show underneath the sweat) and sportier trainers to get that chunkier aesthetic. If you’re getting too hot under your jacket, colour match your jeans or trousers with something else you’re wearing, I’ve just matched them with the sleeves of the Rascals sweater.

SHOP: Majestic Raiders Jacket | Rascals College Crew Neck | Edwin ED-55 Relaxed Tapered | Le Coq Sportif R900 Jacquard


You can get a little more vibrant with your street look, it doesn’t all have to be a black and navy dress code. Brands like Ice Cream, Publish and Saucony all produce a more contemporary street aesthetic with varying materials, colours and shapes. Try a little bit of tonal dressing to make sure you’re not making any colour clash errors.

SHOP: Publish Jupiter Jacket Navy | Ice Cream Glow Clock | Publish Two Tone Joggers | Saucony Shadow Original


You can’t really talk about street looks without covering the monochrome tones. Again, we’d go for a slim fitting pair of jeans rather than skinny and opt for a larger sized tee. I’ve gone for a match in colour with the jacket and shoes but this isn’t toally necessary. The good thing about this look is that it you won’t have any problems with clashing colours at all.

SHOP: MN07 Radio Tear Drop Jacket | Majestic Raiders T-Shirt | Nudie Black Ring Grim Tims | Vans Sk8-Hi Trainers