Skateboarding is full of beautiful things. We aren’t even that picky about what we celebrate – we have no problem debating the best looking kickflip captured in a photo. Was it Andrew Reynolds? Levi Brown? Mark Gonzales? Nate Jones? But as permissive and subjective as we can be collectively regarding what’s cool, we’re all pretty unified when it comes to things that suck. Getting kicked out of spots sucks. Breaking your arm sucks. Realizing you have no toilet paper after taking a dump sucks. These shoes are no different.

1. Supra Chimera

I get it. No matter what, you’ll sell these because Lil Wayne’s name is on them. But what the serious fuck is going on here? It’s like Marty McFly’s future-Nikes and Napoleon Dynamite’s thrift-store snowboots had sex with the cast of My Little Pony and this is their child. Is there a secret market for Brony sneakerheads?

2. Nike “Mama Bear” Dunk

Because Nike will come up with any excuse to make a “limited edition” version of anything, they made a “Three Bears” (as in Goldilocks and the…) series of dunks. In all their cleverness, they made a low-top “Baby Bear,” a mid-top “Mama Bear,” and a high-top “Papa Bear” in different colorways with fur but didn’t realize it was the ugliest looking thing outside of a cybergoth rave. I feel like there should be a warning for people with epilepsy. The ugliness isn’t even the worst part, I just looked them up on eBay and dudes are asking $900 for them. Kill me now.

3. Airwalk Velocity

Vans has been doing a simple, tasteful, functional high top for skateboarding since the early 80s. Why leopard print/orange/purple seemed like a good idea to Airwalk is beyond me. The worst part: somewhere there’s a pair of these sitting in a vintage shop in Williamsburg with a $300 price tag and someone will buy them.

4. eS Scheme

The late 90s were a bad time for skate shoes. I don’t know why “cyberpunk baked potato” was the look of choice, but eS was among the worst. For every classic (Koston, Accel) there were at least a handful of total clunkers.

5. Every Savier shoe

I’ve been told these shoes were invincible, but that doesn’t excuse the fact that they look like plastic Sketchers. It’s really hard for me to say anything remotely negative about Brian Anderson, but what the fuck, the 32-bit shoes you could put on a character in Tony Hawk’s Pro Skater looked better.

6. DC VersaFlex 2

Over the years DC’s contributed some of the most horrendous designs to skate shoe history. One could dedicate a Tumblr to ugly DC shoes and have fresh content for a long, long, long time.

7. Osiris D3

If DC invented the ugly skate shoe, Osiris perfected it. Dave Mayhew’s D3 really is the epitome of ugly skate shoes, and is a major staple in the post-Tony Hawk’s Pro Skater image of skateboarders. Extra bulky, air pocket with laces seemingly an afterthought rather than a functional feature. The best part is that they don’t get buried under your giant JNCO jeans. Surprisingly, Osiris hasn’t slowed down one bit either! Your local mall store probably has a dozen or so pairs of the NYC83 plastic high top abomination, collecting dust in the clearance section.

Want more terror? Check out 7 more shoes right here.

Words: Ian Graham
To complain about all shoes he forgot, follow him on Instagram.
Original Illustration: Michael Giurato
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