Culture, Get the look

Mastering the Skater Boy Aesthetic

Skater Boy Header

When you hear the term, ‘Skater Boy’, the first thing that comes to your head is probably the classic 2002 bop from Avril Lavigne. Well, I’m no different so we may as well just get this out of the way so we can concentrate on the rest of the blog. “HE WAS A SKATER BOY, SHE SAID SEE YOU LATER BOY, HE WASN’T GOOD ENOUGH FOR HEEEEEEEEEER”. Ok, now we’ve got that out of our system, let’s get into how to nail this iconic look.

A Brief History

The sport of skateboarding took off during the 1960s and 70s, where it also began to develop its own style. However, it was the 90’s when skateboarding went from a niche pastime to a global phenomenon. Guys and gals who recorded themselves performing ollies and kickflips on VHS tapes suddenly found themselves to be household names for those in the know. MTV and the rise of metal music in America only added fuel to the rapidly growing movement. Skateboarding was inescapable and so was the culture and fashion surrounding it.

Comfort and practicality were a priority for skaters who needed the freedom and flexibility to pull off their tricks. Because of this, they tended to wear loose fitting, baggy clothing that allowed them to manoeuvre around the half-pipe with ease. This aesthetic remains today, alongside the anti-establishment, carefree mantra that goes with it.

Despite its synonymity with the nineties, skating has never been more popular and accessible than it is now and the same goes for the skater boy look. You just need to look to last year’s Tokyo Olympic Games with the inception of skateboarding and the amazing outfits on show. What’s more, it isn’t just skaters who are repping the look; in fact, the ‘90s skater look has become popular with people from all walks of life – some of whom have never ridden a board in their life.


To nail this look, the right shoes are paramount. For a timeless, comfortable, and authentic look, you can’t go wrong with a classic pair of low-top Vans or Converse. If you’re feeling fancy and want to grab some attention as you’re strutting your stuff, high-tops might be more to your taste. In terms of colour, you can go as light or dark as your mood that day so long as it complements the rest of your outfit.


When it comes to trousers, it really is all about comfort and manoeuvrability. Skinny jeans can be way too restrictive when skating, so they are a real no go. Instead, baggy cargo trousers are absolutely perfect. Historically, Dickies have been the go-to brand for skater trousers due to their durability – you don’t want to rip your pants every time you fall off your board. Alternatively, and for a more modern feel, you can replace the cargos with chinos. Just make sure they are wide-cut and cropped a few inches above the ankle, so they don’t get tangled in the wheels of your board.


Another essential of the Skater Boy Look is the graphic T-shirt. In order to really nail this aesthetic, you want to go for an oversized, baggy shirt with a logo, emblem or image emblazoned on the front. Old-school skaters may combine this with an unbuttoned, check patterned overshirt.


Like with any outfit, your outerwear has the power to make or break your aesthetic. Skaters have often worn branded hoodies to give the rest of their outfit a more relaxed look. If this is what you’re going for, the more oversized and loose the fit, the better. However, if you prefer a more ‘put together’ version of the skater boy look, a classic suede bomber jacket can work brilliantly as they give off a casual vibe whilst also feeling super comfortable.


Given that this look is all about comfort and practicality you really don’t need too many added extras. That being said, you can always find away to accessorize if that’s how you like to style your outfit. A classic snapback, beanie or bucket hat can provide a retro feel to the aesthetic whilst a bum-bag fastened across your chest can keep your belongings safe, therefore providing practicality and style – and isn’t that what this look is all about?

Skater Boy Clothing


About John Hassall

John is the newest member of the Barneys team and takes care of our marketing and content creation. If you’ve been hyped up by us on Instagram before, it’s likely to be him behind the screen! As a journalism graduate and keen wordsmith, you’ll definitely find John frequenting the Barneys blog more than a few times.

Leave a Reply

Your email address will not be published. Required fields are marked *