The history of streetwear
Streetwear began as an underground expression long before it hit fashion week and Pinterest boards, emerging from the intersection of Californian surf culture and New York hip-hop scenes in the late 70s and early 80s.
Pioneers like Shawn Stüssy started selling signature-scrawled tees straight out of the surf world, while early hip-hop icons and skate communities embraced graphic-driven pieces as a form of personal style. From its DIY roots and ties to skate, music and urban subcultures, streetwear grew through the 90s into a global phenomenon, shaping how generations dress and driving an industry that now blurs the line between street style and high fashion.
Streetwear brands on our radar
If you don’t know, get to know. These are the streetwear brands that should feature in your fits.
Carhartt WIP
Originally a brand for blue-collar workers, Carhartt produced heavy duty work gear, before big names in the hip-hop music industry co-opted their looks in the 80s and 90s, and Carhartt WIP was born.
Ed Hardy
Tattoo art, but make it fashion. In the early 2000’s, the designer Christian Audigier brought legendary tattoo artist Don Ed Hardy’s bold graphics to tees, denim, and trucker hats, turning underground ink culture into a full-blown streetwear moment.
Dickies
Founded in 1922 as a workwear brand, Dickie’s earned its reputation with durable trousers, jackets, and uniforms made to last. That was, before it got picked up by skaters, artists, and creatives who made it their own.
How to nail the basics of streetwear style for men
Nailing the basics of streetwear starts with getting your staples right. If you’re a beginner when it comes to streetwear essentials, investing in everyday pieces that work hard and style easily should be top of your list. Think: bold trainers you can wear on repeat, relaxed cargos that can be styled up or down, and simple tees and hoodies. Once you’ve got the foundations locked in, you can dial up the details. (More on that to come).
Men’s Streetwear: How to Build a Modern Streetwear Wardrobe
Rewind a couple of decades, and streetwear was something you’d happily put on when you were planning to fall off your skateboard, face first in the dirt. But today, thanks to modern upgrades and a focus on more premium fits and fabrics, it’s an aesthetic you wouldn’t waste solely at the skatepark.
Today’s men’s streetwear lives in the sweet spot between comfort and cool, where oversized fits, everyday essentials, and statement pieces all co-exist. It’s about hoodies that actually go with everything, trainers you wear on repeat, and showcasing logos of the brands that resonate with you.
Whether you’re dialing things up or keeping it low-key, streetwear today is all about self-expression, mixing influences, and wearing what feels right. No rules, and lots of room for play. Read on for our streetwear guide.
Streetwear trainers
Arguably THE building block of streetwear looks is the not-so humble trainer – your streetwear styling should start from the bottom up. When it comes to brands, don’t get too caught up in the major players, unless you’re happy to drop a considerable amount of time and money. Instead, we suggest focusing on simple but statement styles from the likes of Oakley, New Balance and Merrell.
Oakley Blackout Edge Icon Trainers
Merrell Diorite Cham Redux Storm GORE-TEX® Trainers
Streetwear Jeans
When it comes to streetwear jeans, the fit should be relaxed. How big and baggy you go is all personal preference, as is whether you stick to classic styles or opt for embellishments and stitchwork detail à la Ed Hardy.
BDG Rinse Cacoon Jeans
Ed Hardy UO Exclusive Blue Embroidered Jeans
Jaded London LDN Appliqué XL Colossus Jeans
Arguably THE building block of streetwear looks is the not-so humble trainer – your streetwear styling should start from the bottom up. When it comes to brands, don’t get too caught up in the major players, unless you’re happy to drop a considerable amount of time and money. Instead, we suggest focusing on simple but statement styles from the likes of Oakley, New Balance and Merrell.
Oakley Blackout Edge Icon Trainers
Merrell Diorite Cham Redux Storm GORE-TEX® Trainers
Streetwear Jeans
When it comes to streetwear jeans, the fit should be relaxed. How big and baggy you go is all personal preference, as is whether you stick to classic styles or opt for embellishments and stitchwork detail à la Ed Hardy.
BDG Rinse Cacoon Jeans
Ed Hardy UO Exclusive Blue Embroidered Jeans
Jaded London LDN Appliqué XL Colossus Jeans
Streetwear Cargos
Cargo trousers and shorts are another streetwear essential. They’re probably the equivalent of the cool older cousin to the baggy streetwear jeans of the skatepark era – the kind that we look up to. Style yours oversized and paired with a graphic tee, or keep it clean with a simple hoodie and trainers.
Urban Renewal One-Of-A-Kind De Puta Madre Camo Shorts
Ed Hardy UO Exclusive Green Embroidered Ripstop Cargo Trousers
BDG Denzel Cargo Trousers
Cargo trousers and shorts are another streetwear essential. They’re probably the equivalent of the cool older cousin to the baggy streetwear jeans of the skatepark era – the kind that we look up to. Style yours oversized and paired with a graphic tee, or keep it clean with a simple hoodie and trainers.
Urban Renewal One-Of-A-Kind De Puta Madre Camo Shorts
Ed Hardy UO Exclusive Green Embroidered Ripstop Cargo Trousers
BDG Denzel Cargo Trousers
Streetwear Tops
Picking what to put on your upper half in streetwear style is easy, just ask yourself the following questions: Is it bold? Is it oversized? Does it have a logo peeking out (or front and centre)?
If you answered yes to one or more of those, you’ve found the streetwear top for you. Even sports jerseys can be styled into streetwear looks.
iets frans... Stripe Sport Football T-Shirt
Ed Hardy UO Exclusive Navy Rose Stripe Top
Picking what to put on your upper half in streetwear style is easy, just ask yourself the following questions: Is it bold? Is it oversized? Does it have a logo peeking out (or front and centre)?
If you answered yes to one or more of those, you’ve found the streetwear top for you. Even sports jerseys can be styled into streetwear looks.
iets frans... Stripe Sport Football T-Shirt
Ed Hardy UO Exclusive Navy Rose Stripe Top
Streetwear Hoodies & Jackets
When choosing the right hoodie or jacket for your streetwear fit, it’s up to you whether you go clean and classic or embellished and expressive. If you’re in camp clean lines, look to styles like bomber jackets to tie everything together. Prefer to shout a little louder? Try a hoodie with some serious stitching or bold graphics.
Ed Hardy UO Exclusive Brown Tiger Rose Zip-Through Hoodie
UO Brown Dragon Zip-Through Hoodie
BDG MA1 Washed Bomber Jacket
How to style streetwear
Accessorising is where streetwear looks really come together. Keep it intentional with simple jewellery like silver chains, signet rings, or small hoops that add edge without overpowering the fit. As for the head gear, think accessories like ribbed beanies, baseball caps and statement sunglasses.
How to put together a strong streetwear outfit
Streetwear 101: start with a simple formula that always works. Choose between a graphic tee or hoodie, cargos or straight-leg denim, and a solid pair of trainers – then build from there. Play with proportions, layer when it makes sense, and let one hero piece do the talking while the rest keeps it grounded. Your streetwear aesthetic should be as unique as you are: don’t be afraid to add your own style and other aesthetics into the mix. Y2K, vintage and utility pieces work well with streetwear style.
When choosing the right hoodie or jacket for your streetwear fit, it’s up to you whether you go clean and classic or embellished and expressive. If you’re in camp clean lines, look to styles like bomber jackets to tie everything together. Prefer to shout a little louder? Try a hoodie with some serious stitching or bold graphics.
Ed Hardy UO Exclusive Brown Tiger Rose Zip-Through Hoodie
UO Brown Dragon Zip-Through Hoodie
BDG MA1 Washed Bomber Jacket
How to style streetwear
Accessorising is where streetwear looks really come together. Keep it intentional with simple jewellery like silver chains, signet rings, or small hoops that add edge without overpowering the fit. As for the head gear, think accessories like ribbed beanies, baseball caps and statement sunglasses.
How to put together a strong streetwear outfit
Streetwear 101: start with a simple formula that always works. Choose between a graphic tee or hoodie, cargos or straight-leg denim, and a solid pair of trainers – then build from there. Play with proportions, layer when it makes sense, and let one hero piece do the talking while the rest keeps it grounded. Your streetwear aesthetic should be as unique as you are: don’t be afraid to add your own style and other aesthetics into the mix. Y2K, vintage and utility pieces work well with streetwear style.