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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  1. Skinny Dick

    November 2, 2013 10:24 am

    Jenkem, I agree that the late 90’s/early 00’s were an eyesore for skate shoes, but I think you’re a bit too fixated on that era. Take a gander at more late 80’s/early 90’s shoes. Not only did those shoes serve as the precursor to the moon-boot era with their indestructible rubber guards, but it’s as if the goal was to produce as many non-matching colors as possible.

  2. mdspb

    November 3, 2013 1:46 am

    That’s not the BA; the BA was much cleaner. Rattray’s shoe was decent, and Staba’s was OK as well.

  3. Persona

    November 3, 2013 4:03 pm

    “The late 90s were a bad time for skate shoes.”
    You must be smoking some heavy doobies. Some of the best and greatest shoes came out at that time. There were some that jumped out of the crowd, but all of them were definitely than nowadays shits. It was practical with different details for different tastes, but it was still better. Now you see shelves filled with these vulcanised craps, canvas day lasting shits, ugly and thin boat shoes with no detail or long lasting functionality at all.

    • Aaron M

      November 3, 2013 7:33 pm

      i’m right there with ya dude.

      my nostalgia is for the “late 90s – early 2000s” generation, where I think the best skate shoes came from.
      although some shoes were too chunky, my preference is still a bigger shoe with a thick sole that can actually take a pounding.
      I can’t skate the thin board-feel shoes all these kids go for these days, any their heel bruises leave them ignorant to the damage they are doing.

      eS had some really sick shoes back in the day, and the reason the company went under is because they bailed on their market by becoming the opposite of what originally made them appealing. they started making plain boring shoes which is what all the companies were doing at the time.

      i’m skating THE REYNOLDS at the moment, and seriously, they are sick.
      they have the perfect balance of impact protection, and board feel.
      go get a pair.

      • Persona

        November 4, 2013 12:12 pm

        Fully agree. The nowadays “tennis shoe” looking skate shoes are a fad with the marketing that brainwashes all the clueless kids. I understand that for some tastes they are aesthetically good looking/fitting, but in terms in technology, comfort, protection and meant for skating aspect – they are a regress. And they over all the market/new collections. I’m glad that lately we can once again find thicker, more padding and more technical cupsoles. This “board-feel” crap in nonsense as well, I could skate D3’s on a 7.5 board and it would be all good. I tried the latest “shits”, I hurt my feet, got regular heel bruises and an injury from flicking, because those shoes didn’t have the protection on the side. I promised myself that I will never take whatever industry offers, but the product that is the right one. Sad but those kids that fill their pockets are ignorant, they don’t care and don’t know and at a young age they don’t hurt themselves that easily and it heals a lot faster.

        Agree on the eS, same happened with Lakai and Emerica, when the only models you could find were pretty much the thin, plain canvas slim skate shoes.

        I’m really glad that lately we see more cupsoles in the market, and not all of them are slimmed down. I really like Herman’s G6 and the newest Westgates (with the “runner” toe). It’s all marketing because you see that the prices of them are high and getting higher, because what was once a standard, now is presented as an extra you have to pay more for. I would suggest support Axions, they make just cupsoles, all of them are aesthetically “clean” with the all the protection support.

      • aaron m

        November 6, 2013 6:05 pm

        although i like to support skate shops. i live in Australia and we pay through the roof for retail.
        ridiculously i can order stuff from the U.S. and with shipping included it’s still cheaper than in the shop.

        also annoyingly there’s a couple of brands who through some online shops, don’t ship to Australia (emerica, nike, Nixon etc.)

        half the time, i’m taking a guess at what shoes are gonna work for me, & a lot of the time i’m disappointed.
        I’ve had a little luck with a couple of globes, and I wanted tot try the G6 because it looked good.
        i gave axion a go a couple of years back and they were hopeless, they may be better now…