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Most stylish skateboarders

Skateboarders have always had their own outlaw style. From the all-neon 80s through the baggy XXL 90s, the skate scene has spawned almost as many new trends as grazed knees. We’ve selected a few of our favourite skaters whose current sartorial status is as inspiring as their work on the board.

most stylish skateboarders

Picture: Instagram.com/swankfuck_inc

Dylan Rieder

Dylan Rieder is just one of those dudes who brings it, whatever the situation. Whether modelling with Cara Delevingne and A$AP Rocky for DKNY or switch flipping a set of stairs, his look is always on point. Crisp white Oxford button-down shirts, cropped black tailored trousers and a classic leather biker jacket are all monochrome staples in the wardrobe of one of the most stylish guys on – and off – the board.

most stylish skateboarders

Picture: Instagram.com/olsonstuff

Keelan Dadd

Citing Yeezus himself, Kanye West, as his main style influence and Philly legend Stevie Williams as his mentor, Keelan rocks that urban/high-fashion mix to full effect. Whether being papped at LAX airport in an all-over print hoodie or poppin’ bottles in the club wearing a classic denim jacket and gold chains, Keelan has it on lock. 

most stylish skateboarders

Picture: Instagram.com/jimgreco

Alex Olson

Being the son of legendary 70s hellraiser Steve Olson you’d expect Alex to follow in his father’s scruff-punk footsteps but that definitely isn’t the case. With a more refined look, Olson Jr favours simple slim-cut tees, Breton long sleeves, plaid flannels and even the daring white-on-white look. Alex’s own board/clothing brand Bianca Chandon takes influence from the 70s New York disco scene and the early days of Chicago house music so expect to see his personal style acquiring a more retro feel.     

most stylish skateboarders

Picture: Instagram.com/keelandadd

Blondey McCoy

With his Fred Perry polo shirts, track pants, signet rings, gold teeth and Umbro footy shirts, Blondey McCoy often looks more like an extra on This Is England 90 than one of London’s brightest skateboarders. As part of the Palace crew, Blondey has become a favourite of style mags such as i-D and Dazed & Confused as well as a model for the likes of Supreme, adidas and Highsnobiety. Catch him on a good day at Southbank and his skating will blow your mind.

most stylish skateboarders

Picture: Instagram.com/blondeymccoy

Jim Greco

During his hard partying years, Greco’s hairspray, skintight jeans and leathers had him resembling New York Dolls guitarist Johnny Thunders, but now that sobriety has kicked in, Greco’s style is slicker than ever. Jim once said his style icon was Javier Bardem’s silent killer from the movie No Country For Old Men and he’s stuck with that vibe ever since – cropped wide-leg ranch pants, full-zip cardigans and vintage polyester shirts make this dude stand out from the masses.

most stylish skateboarders

Picture: Instagram.com/_streethassle

Sean Pablo

At just 18 years old, this half-Salvadoran/half-Irish skater from LA is one of the most interesting dudes to break through in the past couple of years. With his wiry frame standing at over 6ft tall, he looks more like a young Sid Vicious than someone who can boardslide a handrail. Tucked-in T-shirts, rolled up slim work pants, dirty Chuck Taylors, nail varnish and a constantly changing hair style/colour are Sean's rockstar staples.