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. CHECK OUT THE boohooMAN x BOO JOHNSON SKATE CAPSULE PT.2 NOW!

Contents

• What is the skater dress style?
• How to dress like a skater and look stylish?
• Key skater clothes for guys
• Skater outfit ideas
• Skate fashion FAQ
• Take-home message

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.

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 a relaxed fit
• Add cargo and utility details to your outfit
• Go for graphics and logos up top
• Pick trainers with flat and wide soles
• Finish off your getup with a cap and sports socks

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.

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.

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.

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.

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.

• Skater trousers
• Skater hoodies
• Skater shirts
• Skater accessories
• Skater shorts

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?
• How to wear skate shoes with jeans?

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. Recently, the skater aesthetic has become popular and is a trendy look. The skater style is taking over on social media apps like TikTok and Instagram. Wondering how to dress like a skater boy? Don’t worry I’ve got you covered. Vans, Levis 501 jeans and an oversized hoodie are the basics to any skater boy outfit. If it’s a sunny day, short shorts, and an oversized graphic t-shirt will look cool. Accessorize the look by wearing wired earphones. If you’re really trying to look like a skater, don’t forget your skateboard. In this post, I share 5 skater boy outfits and go over the elements of the skater style. You’ll also find skate shoe recommendations and advice on how to dress like a skater, even if you don’t skateboard.

5 Skater Boy Outfits

The Basic Skater

• Vans Classic Slip On
• High Tube Socks
• Levis 501 Jeans
• Oversized Thrasher Hoodie
• Stüssy Dad Cap

This look will capture the skater boy aesthetic. This outfit can be worn to school, out with your friends or at the skatepark. It’s a very basic skater look but there’s nothing wrong with being classic. The Levis 501 jeans will fit loose and are baggier than the typical slim fit jeans. Levis 501 jeans are super popular right now and are a staple in the skater boy look. Thrasher is a brand that some people are sick of now, because of how mainstream it became back in 2016. If you prefer wearing a different brand try:

• Supreme
• Stüssy
• Obey
• Nike

The True Skater

• Vans Kyle Walker
• High Tube Socks
• Long Cargo Shorts
• Oversized Graphic T-shirt

If you’re going for the true skater look, you are going to want to follow these recommendations. The Vans Kyle Walker are known to be great skate shoes worn by other skaters. Long cargo shorts are a classic in the skate community. An oversized shirt is a must when you’re dressing like a true skater. Companies like Vans, Santa Cruze and Powell Peralta all make great graphic t-shirts for skaters.

The Hypebeast Skater

• Nike Dunks
• Low Socks
• Short Shorts
• Supreme Box Logo T-Shirt or Hoodie
• Supreme Washed Chino Twill Camp Hat

If you are a hypebeast and like to skate, this is the outfit for you. The Nike Dunks are currently some of the most popular sneakers out right now. These are super popular shoes worn by people who are trying to have the skater aesthetic. The Supreme box logo shirt or hoodie will be quite expensive, as it is one of the most sought after items in streetwear. The Supreme box logo t-shirt is iconic for hypebeasts and in fashion. The Supreme washed chino twill camp hat has been worn by skaters for ages. If you’re going for that hypebeast skater look, this cap is the perfect hat to top off your outfit. If you’re not a fan of cap’s, you can never go wrong with a Supreme beanie.

The Urban Skater

• Beat Up Skater Sneakers
• Blue Dickies Jeans
• Retro Sweater
• Beanie

This look will be as close to a real skater as it’s going to get. The beat up sneakers will make it look as if you skate. If you actually skate, then you probably have some laying around, if not check the thrift shop. Blue Dickies jeans are a classic for skaters and have been worn by them for decades. If you want to look as authentic as possible, pick up some blue Dickies jeans. The retro sweater can be picked up at the thrift shop. You can wear some brands that were popular in the 90’s like Champion and Gap. Wondering if Champion is in style? Check out this article: Is Champion in Style?

The Aesthetic Skater

• Nike Blazers
• Loose Fitting Denim Pants
• Baggy White Shirt
• Oversized Grey Nike Hoodie
• Nike Beanie
• Wired Earphones
• Rings

This outfit is strictly for those who are going for the skater boy aesthetic. The oversized and baggy fit of the clothing will give that skater look, while wearing Nike will keep the fit modern and trendy. Accessorizing the outfit by wearing wired earphones will give a retro look to the outfit. Rings are a popular accessory that will give a skater boy look. This outfit is very popular and trendy on TikTok.

What is Skater Style

In present time, skater style takes inspiration from 90’s fashion. The skater look is now considered to be retro, as skating was super popular in the 90’s and early 2000’s. Retro clothing always comes back into style and the skater aesthetic is no different. In the last few years, streetwear has become super popular and a lot of streetwear brands are either apart or take inspiration from the skating scene. Originally, skater style was considered to be unconventional and rebellious. Loose fitting pants and baggy t-shirts were a style popularized by skaters in the 90’s. Skaters would wear loose fitting clothes as it allowed for more mobility when they were doing tricks. Baggy clothing was both practical and would protect the skater when they would fall. Skate shoes are worn casually by consumers today without even realizing the community that they originated from. Brands like DC, Supra and and Etnies were once very popular skate shoes. Nowadays, brands like Vans, Adidas, Nike make skate shoes with a minimalist style. DC shoes were very bulky but shoes like vans have a thinner and more practical look. Oversized graphic t-shirts are a staple in the skater community. Skater style would be to wear a a crewneck shirt instead of a v-neck. Generally, graphic t-shirts worn by skaters can be found for affordable prices at your local skate shop, Zumiez or Pacsun.

Brands Worn by Skaters

• Vans
• Santa Cruz
• Thrasher
• Powell Peralta
• Baker Skateboards

Best Skate Shoes

When it comes to skate shoes there are various different options. If you are going for a retro skate look, DC shoes will do the job, but you will look outdated. Modern and trendy shoes worn by skaters or those who embrace skate style and culture are:

• Nike Dunks
• Jordan 1’s
• adidas busenitz
• Adidas Superstars
• Vans Kyle Walker
• Vans Old Skool
• Converse

Can You Dress Like a Skater if You Don’t Skate?

If you don’t skate, you can still dress like a skater. Many people that have never skated enjoy the look and fit of skate style. In the last 15 years, skating has had a tight but stagnant community. By consumers purchasing skating apparel, it has helped grow and keep skating brands and businesses open. A few years ago, Thrasher became very popular and shined a light on skate culture. Since then, streetwear brands like Supreme and Palace have been worn by both skaters and casual consumers. Celebrities like Justin Bieber, Drake and Pharell have all embraced skate style and culture. None of these celebrities are pro skaters – they just like the look. If you like to wear skate brands, streetwear brands and enjoy the skater aesthetic, there is nothing wrong with making it your style. On TikTok and Instagram it has become very popular to dress like a skater. Now, teenagers and young adults are dressing up and supporting skater brands. Traditional skaters, may find that consumers that dress like skaters but don’t skate are posers. In reality, influencers shining a light on skate style is very good for skate companies and skate culture. The rise in popularity is growing and supporting the skate community.

Final Thoughts on Skater Boy Outfits – How to Dress Like a Skater

If you’re looking to change your style, the skater look is very trendy right now. In this post, we went over 5 skater outfits, what is skater style and if you can dress like a skater even if you don’t skate. Do you like the skater aesthetic? Please let me know in the comments below.

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