The Age Of Ankle, The Death Of Hightop

Paying tribute to the iconic shoe that defined the early 2000s.


Nothing captures sneaker culture quite like the high top. With their bold silhouette, these iconic kicks have been embraced by the likes of Lil Wayne to Kanye West, serving as a canvas for both the self-expressive skater and the trendy hype beast.

But, nothing in fashion lasts forever, and as hype fades, so does the trend. Here, we pay homage to this beloved staple and explore how it transformed from a sneakerhead essential to a resale relic.

The Hightop era was a defining moment in sneaker culture, encapsulating a spirit of rebellion that resonated well beyond the early 2000s. With roots in basketball, high tops became a significant part of streetwear and fashion, evolving into cultural staples sported by trendsetters and music legends alike. From punk rockers in the 1970s to heavy metal artists and pop stars like Avril Lavigne in the early 2000s, these sneakers represented a lifestyle that embraced creativity, individuality, and the vibrant energy of youth.

Lil Wayne wearing iced-out custom Supra Skytops at the 2009 BET Awards.

Lil Wayne wearing custom Supra Skytops at the 2009 BET Awards.

A pair of high tops could elevate any outfit and signify social status, while their eccentric silhouettes allowed wearers to make a statement about who they were. Among the myriad options, Supra sneakers stood out as a hallmark of this era, blending style with a distinctive swagger that captured the hearts of sneakerheads.

I still vividly recall the anticipation of back-to-school season in grade eight, when I begged my mother for a pair. The hype was real. 

We’d hit up Winners (the Canadian version of TJ Maxx), where recognizable brands came at prices that suited my family’s budget. That routine became a quest of sorts—me, on a mission to find some gem kicks among the lineup of shoes. It was in the men’s section, where the truly coveted finds lay, that fate smiled upon me: I spotted a pair of Charcoal Grey Supra Skytops for $79.99. I could already envision the perfect fit: dark wash denim paired with a simple tee for the first day. At that moment, I felt on top of the world, having secured the gem of all gems.

Yet, acquiring a pair of Supras wasn’t always that straightforward. Their scarcity and hefty price tag could deter many. But when I finally got my hands on those high tops, it felt like I hit the jackpot. In the late 2000s and early 2010s, the streets teemed with cool kids proudly sporting these iconic shoes—so you can imagine what it meant to find a pair.

The celebrity endorsement of Supras only added to their allure. From Justin Bieber to Soulja Boy, the skater vibe permeated popular culture. Who could forget young Bieber donning his purple Skytops in the “Baby” music video? And then there was Lil Wayne, the face of the brand, proudly showcasing his own signature styles. It was a true high top mania.

Justin Bieber and Ludacris in the Baby music video.

Justin Bieber and Ludacris in the "Baby" music video.

Fast forward to today, the landscape has shifted. Low tops, like Adidas Sambas and the PUMA Speedcat OG, have emerged as the new darlings, usurping the spotlight once held by their high top counterparts. But does that signify the end for high tops? Absolutely not.

While low tops dominate the scene, the classic Chuck Taylor remains a timeless silhouette in sneaker history, celebrated for its versatility. Moreover, Isabel Marant Bekett sneakers are quietly making a comeback, reminding us that this style is far from over. Their chic design and effortless appeal resonate with those who appreciate the fusion of comfort and fashion (shoutout to all the hightop enthusiasts still rocking skinny jeans).

In a world awash with low top options, one could argue that ankles have never been happier. Yet, let’s not overlook the high tops—they’re unique, fresh, and nostalgic. While they’re not as popular as they once were, high tops still got aura.


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