Why We’re Still Obsessed With Late 90s Skate Style

With the return of the legendary Tony Hawk’s Pro Skater (1999) on the horizon, we thought we’d revisit the turn-of-the-century skate style that continues to drop-in on fashion trends across the globe. It seems those big pants, tiny wheels, and Herculean shoes from the late 1990s continue to cast a long shadow over men’s fashion.

Kick, Push, Coast 
The unique attitudes radiating from late-90s skateboarding have been crucial in the formation of sartorial style and sneaker collecting habits across the globe. Originating in the sun-kissed state of California during the late 1970s, skateboarding really began to occupy the collective consciousness during the late 1990s. 

The so-called era of ‘big pants and tiny wheels’ was dominated by hulking sneakers, boxy hoodies, and wide cargo pants – a sartorial sensibility that’s once again firing in 2020. 

Virgil Abloh and his Off-White label continue to produce XXL cargo pants with gaping pockets. A$AP Rocky raided shoe boxes with the Under Armour SRLo (a sneaker bearing an uncanny, controversial resemblance to 1999’s Osiris D3). The Carhartt kids have reconnected their wallet chains, and streetwear is once-again drowning in oversized denim.

With modern-day mega brands like Palace flowering from their skateboarding roots (owing a cultural debt to cult 90s skate labels like Girl, Chocolate, Blind and World Industries), everyone from high fashion to fledgling startups has attempted to carve out their own piece of the skatepark. 

But to understand the hype, we really need to travel back to Lafayette Street in Downtown Manhattan. 

The BOGO 
Founded in 1994, Supreme is the brainchild of James Jebbia. Beginning as a small store on Lafayette Street, Supreme has grown to become a global streetwear icon embodying integrity and exclusivity. 

Pivotal in establishing skate style in the late 90s, Supreme made a habit of introducing exclusive apparel, collaborations with numerous artists (including KAWS and Keith Haring), provocative skate decks, and coveted box logo (BOGO) tees. 

But it wasn’t just streetwear basics that enamoured Supreme loyalists. Customers would often step into their stores stunting Louis Vuitton with Chuck Taylors, or Gucci with Supreme tees. Jebbia realised that the cool kids were willing to drop real cash on quality products, and worked hard to preempt the extreme sartorial mashup of streetwear and luxury that’s still defining men’s fashion in 2020. 

Collaborations with Gucci and Louis Vuitton burned holes in wallets across the globe, and fashion houses remain desperate to cash in on the sartorial attitude and palpable nostalgia that lives within the BOGO.

What’s the best way to drop-in on a demographic obsessed with skateboarding? The sneakers, of course. 

Chunkified  
High fashion has long been infatuated with skate labels, especially the fierce loyalty they can inspire. When Louis Vuitton released their Zig Zag Sneaker last year, the Internet was quick to point out the startling similarity to the Osiris Guru model. It seems fashion houses and their collaborative offspring are still eager to revisit the late 90s aesthetic to fill the seemingly insatiable appetite for gargantuan silhouettes and dad-shoe desires. 

While cult sneakers from Etnies, Emerica and éS have now fallen into relative obscurity, their influence still casts a shadow over men’s fashion today. As A$AP Rocky recently told GQ, ‘It’s almost like you get a vintage television or game console or arcade game and you just refurbish it’. And this idea of refurbishing wardrobes and retros from the late 90s is a large part of the eye-watering success of the Balenciaga Triple S, the Yeezy 700, and the hype-driven triumph of labels such as Off-White. 

Still busting ankles, grazing knees, and inspiring thousand-dollar tees more than two decades later, turn-of-the-century skate style is a look and attitude that many brands are still trying to emulate today.

Kick, push and coast on over to THE ICONIC for the latest in late-90s skate fashion.