Skater culture has left a heavy mark on contemporary men’s fashion. These kings of the concrete have always had an innate sense of urban style. With their oversized silhouettes, tough fabrics, and super casual aesthetic, today’s biggest streetwear trends are steeped in skate tradition. Now, mainstream fashion is experiencing a resurgence of 90s skater sub-culture style. And although skaters have typically preferred to look anywhere but the catwalk for their fashion inspo, that hasn’t stopped high-end designers such as Vêtements, Alexander Wang, and Balenciaga poaching the sartorial styles of the underground. Whether you’re a kickflip king or a Nollie novice, here’s how to work key skate staples into your smart-casual and off-duty looks.



What is the Skater Dress Style?

Skater style has come a long way from the voluminous jeans, XXXL tees, and chunky suede kicks of the 80s and 90s. Today’s take on skateboard fashion still prefers a baggy silhouette, but with more flattering cuts, fresh colourways, and a definite utilitarian edge. Practical, comfortable, and built to last, these pieces favour function over flashy and have an unapologetically chill, laid-back look.

how to dress like a skater guys

A short history of the skater aesthetic

As a sport, skateboarding evolved in the late 1960s and 1970s, and the skater boy aesthetic quickly evolved with it. Early 80s skater fashion took elements of grunge and punk culture and channelled definite anti-establishment, anti-authoritarian vibes too. The emphasis was on affordable clothes that were functional enough to be worn on the board, yet stylish enough to be worn on the streets. It wasn’t until this niche sport moved mainstream in the 1990s, however, that these alternative heroes of the underground captured the public imagination.

Skater aesthetic in pop culture

The mainstream success of 1990s/2000s skate-punk bands such as Sum 41, Offspring, Green Day, and Blink 182 — as well as Avril Lavigne’s iconic 2002 single, ‘Sk8r Boi’ — brought skateboard style to the global attention of millions. The skater style dress rose in popularity around the same time, and has remained a fixture of women’s fashion ever since. And throughout the 2000s, the popularity of Tony Hawk’s Pro Skater video game series embedded the skater aesthetic further into mainstream consciousness.

Male celebrities wearing the skater boy trend

Mainstream attention has meant that skater clothes are no longer confined to the half-pipe. From social media influencers to high-end designers, style-conscious men everywhere are now co-opting skater aesthetics without ever having picked up a skateboard. In recent years, pro skaters like Ben Nordberg, Alex Olson, and Dylan Rieder made the leap from the curb to the catwalk when they modelled for major labels like Louis Vuitton and DKNY, proving that skate fashion and high fashion do mix. And in the celeb world, Pharrel Williams, Drake, Kanye West, Adam Levine, and Justin Bieber are just some of the stars embracing the skater craze

How to Dress Like a Skater and Look Stylish?

Choose pieces in relaxed fit

Skater style may have been adapted for those who will never step foot on a ramp, but the key to rocking this aesthetic remains the same: keep your shirts loose and your trousers relaxed. Wide-legged cargos, oversized hoodies, and boxy graphic tees are still at the heart of skate fashion. For a modern twist and more balanced aesthetic, however, try mixing bulky skate pieces with more tailored casualwear. Layer a thick hoodie over cropped trousers, or team a tailored shirt with baggy utility trousers below.

how to dress like a skater guys

Add cargo and utility details to your outfit

Today’s take on the skater aesthetic merges skateboard culture with the best of the hip-hop, utility, and grime trends for a look that’s functional and effortlessly cool. Cargo and utility trousers, in particular, have long been a skater boy favourite, thanks to their excellent durability and large, practical pockets. Opt for a relaxed fit and add some utility accessories: a cross-body or chest bag, chunky kicks, or an industrial belt.

how to dress like a skater guys

Go for graphics and logos up top

One of the most notable and enduring trends in skater fashion is the graphic tee, which pairs perfectly with the sub-culture’s emphasis on creativity and individuality. Opt for a relaxed or looser fit that effortlessly bridges streetwear and skate wear, and don’t shy away from oversized logos in bold fonts, iconic fire-flamed colourways, and bold stripes. When the temperature drops, layer under an open over-shirt or loose hoodie.

how to dress like a skater guys

Pick trainers with flat and wide soles

Skate footwear is all about function, durability, and finding what works best on the skateboard. Low-top trainers with a vintage aesthetic and flat, wide soles provide the perfect balance of masculine style and athletic support.

Vans and Converse have been classic skater staples for decades, but today’s brands including Nike, Puma, Lacoste, and Adidas have all teamed up with up-and-coming skate wear names, adding new technologies and modern colourways to the traditional skater silhouette.

These trendy skater shoes are making skating more comfortable, stylish, and colourful than ever. Make a statement with hot pink laces and chunky soles, or keep it retro with a pair of classic black Vans. Team with crew socks and baggy, cuffed leg trousers.

how to dress like a skater guys

Finish off your getup with a cap and sports socks

Embellish your skater ensemble with some half-pipe-worthy accessories. For an iconic skater boy look, add a logo baseball cap or bucket hat up top and team your classic skate kicks with white sports or tube socks down below. While a black cap is a classic off-duty choice, accessories are a great way to introduce colour into your outfit too. Liven up a monochrome outfit with a brightly coloured beanie, or show off your favourite skater shoes with a pair of contrasting socks.

how to dress like a skater guys

Key Skater Clothes for Guys

Skater trousers

Skaters have long favoured robust fabrics that offer tough protection from knocks and falls, as well as relaxed fits that allow for plenty of movement on the board. Today, these baggy silhouettes and thicker materials blend seamlessly with the functional aesthetic of the utility trend. Think thick twill chinos, cargo pants with cuffed hems, and oversized skater jeans. Choose stain-friendly colourways such as khaki, black, or camo prints, and balance that baggy silhouette below with a fitted shirt up top.

Skater hoodies

The hoodie is another enduring skate staple, favoured for providing a cloak of cover for those skaters taking their boards out of bounds. For the less rebellious, a hoodie also provides the perfect way to dip your toes in the skater trend, even if you haven’t stepped on a board in years. Try mixing a hoodie in pastel shades with baggy jeans for effortless on-trend off-duty style, or pair a slate grey hoodie with tailored trousers for a smart-casual weekend look.

Skater shirts

Skater shirts tend to lean towards thick, long-wearing materials and a loose fit that provides a wide range of motion. Cotton and flannel are the name of the game, while checks and stripes are very popular on the skater park too. Layer a plaid flannel shirt over your favourite graphic tee, or opt for a hooded over-shirt that will see you through the seasons in casual skater style.

Skater accessories

Avoid accessorising with too much jewellery if you’re hitting the skate park, and make your fashion statement up top instead. A minimalist baseball cap is an easy way to add an urban edge to a more polished look, and skaters often rock the wool beanie all year round too. Streetwear accessories like sling bags, backpacks, and reflective or metallic belts also work well with the skater trend, or go for for a classic wallet chain for 90s vintage flair.

Skater shorts

A pair of skater shorts strikes the perfect balance between style and comfort on hotter days. To nail the summer skater boy aesthetic, pick a knee-length pair with a loose fit and plenty of practical pockets. Cargo shorts will work well to balance out an oversized hoodie on top, or opt for wide-cut chino shorts for a slightly smarter look. Pair with your favourite pair of skater kicks and a graphic tee to keep your skater style from veering into preppy.

Skater Outfit Ideas

Skate Fashion FAQ

How to look like a skater boy?

If you have to choose one skate-inspired piece, opt for a pair of classic Vans. These kicks are synonymous with skater style and will pair easily with all your casualwear outfits too. Relaxed fit trousers and graphic tees channel immediate skater vibes and will make equally versatile additions to your wardrobe. And when it gets cold, layer up with vintage coats and durable workwear jackets, then top it all off with a cap or a beanie for easy, skater boy style.

How to wear skate shoes with jeans?

Flat-soled skater shoes look best with extreme fits: either skinny jeans or loose-fitting denim. If you’re planning on wearing them to the half-pipe, the latter will be the more practical choice. Opt for a cropped, wide-leg design or a straight-leg style cuffed a couple of inches above the ankle.

Take-Home Message

The skater trend marks a welcome return to the basics in menswear, once more putting the focus on functional, practical, and durable fashion. Contemporary skate pieces have refined the traditional 90s skater outfit, however, proving that comfort and style can coexist. Plus, these designs blend well with a number of other sub-cultures and styles, so you can mix and match across today’s hottest trends to create a truly individualistic look.


1 Comment

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