The 20 Ugliest Sneakers of the Past 20 Years

Year: 1996

Are these even real? They are. And worse than that, at one point they represented the best of the USA. In 1996 Shaquille O'Neal wore these to the Atlanta Olympics as part of that year's "Dream Team." The team ended up winning the gold, but these explosions of bad taste did nothing to help (except to support Shaq's game in the ugliest way possible). Older sneakerheads will fall into nostalgic bliss looking at these kicks, but the rest of us are happy to see them left in the past.

Year: 2001

Made as a signature shoe for Latrell Sprewell, this pair of Dadas took the inspiration of car customization just a little too far. In a gesture of innovation (I guess?) they brought a commonly modified aspect of a car, the rim, and placed it on the shoe. With each step in the shoes, the fake chrome rims spin, using the air pressure that builds up in the sole. It's not just the rim that's a crime with the shoe—the rest of the design is uninspired at best.

Year: Too many

It's one of the most popular high-end sneakers ever made. but we're putting our foot down: It's also one of the ugliest sneakers ever made. Despite the fact that Prada designed it, it's entirely devoid of taste, with combinations of patent leather, smooth leather, and mesh—in shapes that are desperately orthopedic—plus an absence of detailing highlighted by unflattering lines and panels. Truly one of the strangest success stories in footwear history.

Year: 2001

No list of ugly sneakers is complete with Adidas' second attempt at a Kobe signature shoe. Despite later stories, Kobe was actually pretty involved with the sneaker that ended up hitting the market like a brick. Now widely considered the ugliest sneaker of all time, it's not that bad compared to some other lesser-known sneakers, but it's still atrocious. This is what happens when you design in a vacuum.

Year: 2006

Before he got the world scratching its head and Googling "Li-Ning," Dwayne Wade was making sneakers with Converse. That being said, when he was at Converse the world was scratching its head over something else: the design choices of these signature sneakers. The Wade 1 looks like the result of some whacked-out BDSM focus group that ended up choosing the lowest common denominator. This is a case where whatever the original idea was, it got away from the design team, resulting in a shoe that should be sitting in a bargain basement, not on the feet of one of the best players in the world.

Year: 2006

It's hard to hate on Stephon Marbury's sneaker brand Starbury, because it was founded on an incredible premise: bringing quality basketball sneakers to kids who couldn't afford the high price tags of major brands. That being said, when you're buying a $15 pair of sneakers you get what you pay for—at least aesthetically. The Starbury 1 reads as a white leather sock with under-developed branding and cheap detailing. When a kid is forced to buy a pair of $15 sneakers, the last thing they want is to stick out, and Starbury 1s are sore thumbs. The price point was an achievement; the rest of it was a mess.

Year: 2006

Reebok's Question and Answer lines have been some of its most historically successful shoes, but at one point the brand got a little too comfortable. The Answer 9 looks more like a ski boot than a sneaker, and when an athlete is looking to pick something up for their game play, a bunch of leather, straps, and a bungee—plus an actual dial—adds up to a heavy sneaker that just doesn't make sense for anyone to wear.

Year: 2004

Looking like some kind of mutated car-racing shoe for infants, the Adidas T-Mac 4's largest fault isn't even in the lackluster design. Instead of laces, something that's been working for shoe-wearers for literally thousands of years, the T-Mac 4 features a "HUG" tightening system that folds out of the heel and takes advantage of a screw and hinge apparatus to lock the shoe to the players foot. Think it sounds confusing? So did everyone else. That's why these aren't available at Footlocker anymore.

Year: 2001

The annual Air Jordan game shoe is one of the most anticipated and analyzed shoes in the world when it's released. All that pressure and focus means the company has buckled more than once, and it's willing to admit that. In 2001 it looked like Michael Jordan was out of the game forever, and the brand's lead designer Tinker Hatfield bowed out. That perfect storm resulted in shoes that look like they have old-fashioned spats and do nothing to inspire positive vibes on the court or street.

Year: 2007

LeBron James' signature line of sneakers at Nike has included some incredible shoes. Not all of them were immediately understood, but even some of the most-hated styles found their fandom. Except the LeBron V. You'll be forgiven if you mistake the LeBron V for a baseball cleat or climbing boot on account of its inexplicable strap and a shape that's far too narrow and far too tall. It's not even that the proportions are all that bad—but the detailing accentuates everything that's out of balance with the sneaker, turning it into something much worse than it has to be.

Year: 2002

When it comes to sneaker design, few brands do worse than Dada. The company is still making it work over in Japan, but Chris Webber's signatures from 2002 are bewildering to say the least. His nickname "Webb" is emblazoned in a hard panel of metallic silver on the side of the shoe, creating an anchor for hits of silver all over the place. The rest of the look is uninspired, with a chunky design devoid of elegance and good taste.

Year: 2005

Team Jordan sneakers don't get the same kind of examination that the game shoes get, but that's because the bar is generally much lower. Take the Melo 5.5, for example. Unlike the Jordan game shoes, Team Jordans are positioned for a much more affordable price point—and often they scream it. The Melo 5.5 looks like the design team ran out of options and did the only thing they could do with what they had: bedazzle the upper with more eyelets. It's a thematic and executional mess, and one that should have never seen the light of day.

Year: Multiple

Reebok's Ice Cream sneakers found a limited run of popularity when they were endorsed by Pharrell Williams and worn by the likes of Kanye West. There must have been a lot of money in those endorsements. Because when it comes down to it, the sneakers are aesthetically the equivalent of house slippers brought down to sneaker proportions. The coloring is unsophisticated and the shapes are chunky. We're just glad Ice Cream has also started working with Adidas to create sneakers that are much more current.

Year: 2002

In a strange twist for just about everyone, 50 Cent teamed up with Reebok to create G-Unit sneakers in the early 2000s. We recently found out that the pairing earned 50 about $80 million, but that had to be thanks almost exclusively to 50's name. The shoes themselves are heavy and clumsily designed, in total contrast to the upscale life that 50 projected. There was a disconnect between who 50 was and what he was selling, making the G-Unit move an obvious money ploy that made no attempt to actually create good-looking kicks. At the same time that 50 was beginning the G-Unit run, Jay-Z was building his own "S.Carter" sneakers. They sold way fewer pairs than 50's, but looked just as bad.

Year: 1998 C

Created as a signature shoe for Tim Duncan, the Total Air Foamposite Max takes the worst aspects of the Foamposite and Air Max lines and blends them together into a shoe that looks more like a building block than a piece of athletic wear. They were not a runaway success by any means. The small, vocal following that these shoes attracted was able to demand a rerelease just a few years ago, but after hitting the sale racks basically everywhere, these kicks will probably be relegated to the dustbin of history. Here's hoping!

Year: 2001

Looking like a dystopian prediction of days to come, the Flightposite 3 features about three too many design elements to "update" the sneaker without adding anything positive to the future of footwear. Multiple pods on both sides of the shoe are reminiscent of Stranger Things' Demogorgon, adding structure that is neither sporty nor utilitarian. Nike was able to get off a few colors of this brick that were decent, but the shoe is generally a loser. Sad!

Year: 2015

Rick Owens has created his fair number of bangers with Adidas, some as recently as last month. But his style isn't for everyone. And sometimes, it's not for anyone. There was a major misstep when it came time to combine Adidas' iconic Superstar with Owen's signature mix of hard and soft. The result is a strange leather bootie that looks almost like scuba gear with a rubber shell toe glued to the top. Add to that a price tag that approaches a thousand dollars, and this is a hard pass.

Year: 2012

Sometimes meaning is worse than design. And when it came to the long-running collaboration between Adidas and Jeremy Scott, often his intentions got swamped into his aesthetics. There was the sneaker that reminded shoppers of slavery, or the animals that sometimes got a little creepy. But appropriation is uglier than them all, and this totem themed sneaker took religious icons and slapped them thoughtlessly on athletic wear. The colors are too bold, the style too big, and the lack of respect too egregious. These were not a win for anyone.

Year: 2014

Look, Versace has long been a bastion of respectable style, but these First Idol slip-ons are a major slip-up. The upper's design is an obvious attempt at understated simplicity, but ends up being completely under-designed. (Think: a fast-fashion pair of $20 sneakers.) Contrasting piping on the sole cheapens the look, and an over-excited tongue pushes out the front of the shoe like an overstuffed skate sneaker. The one luxe design element is the massive golden Medusa head on the tongue, but within context the sneakers just look confused. Plus they're $1,200. What?

Year: 2011

Here's the deal: These pony hair Footscapes are ugly as sin and incredibly hard to wear. But we have to admit, and this is the only time we're admitting this within this list: We love them. There's nothing like a good sartorial challenge, and when it comes to challenges, these are like K2. Still, when they're worn right, they're absolutely worth it. Ugly? Yes. But amazing.