“The ugly can be beautiful. The pretty, never.”

When Oscar Wilde first spoke those words, we’re fairly sure he wasn’t looking down at his shoes.

But the fact remains, over 100 years after the man himself died: what defines beauty is its ability to shock, not necessarily a pleasant exterior. The world is full of pretty things, but to find something that can genuinely stop you in your tracks (for whatever reason) is rare, and that’s what makes it all the more precious.

Sneaker culture has always been a medium for the world’s street peacocks to flaunt themselves, so we thought we’d point the lens at five examples of extreme shoe design that have divided opinion everywhere they’ve landed. You might love them; you might think they were designed in a room with no light, by people with no feet. The point is they make you feel something.

Remember: beauty is in the eye of the beholder. One man’s cop is another man’s crap, and it’s a fine line that divides the two. With that in mind, here’s 5 of the world's most beautifully ugly sneakers...

adidas Originals by Jeremy Scott

Jeremy Scott is no stranger to subversive design, so any sneaker with his name on the box was never going to fit everyone’s tastes. That said, his now-notorious adidas Originals JS Bear shoe pushed things way further than a lot of people were comfortable with. That didn’t stop the likes of Lil Wayne, Rihanna and Cara Delevigne rushing to show them off - even if they did look like they were wearing a large pair of novelty slippers - but others were less convinced. While critics of Scott’s designs argue that six-inch wings, leopard tails and oversized plastic bones aren’t exactly accessible everyday attire, such reasoning largely overlooks the point that this is costume fashion, not wardrobe essentials. If your personality is big enough to pull it off, then it makes a very special kind of sense.

Raf Simons for adidas

As with Jeremy Scott, Belgian-born Simons was already something of an antagonistic presence in fashion and his clunky, achromatic style is an acquired taste for sure. Still, thanks to adidas’ commendable open-mindedness, both collections so far have indulged the designer’s conceptual leanings, producing shoes that challenge the established norms of tonal combination, pattern overlay and the mixing of materials (spoiler alert: the third collection is just as out there). We’ve heard them described as everything from “shoes for Optimus Prime” to looking "like a child’s coloring book,” but for every naysayer there’s someone willing to heap on praise for Raf’s defiant attitude (just ask A$AP Rocky, the man’s number one fan). What's more, we defy anyone to knock them once they’ve felt how insanely comfortable they are to wear.

Knee-High Sneaker Boots

For this one we’re not singling out a specific brand or model, but rather including that whole, peculiar family of super hi-tops so often viewed with a mixture of suspicion and disdain by the sneaker-sporting community. So, that’s everything from the ghetto-fab adidas Missy Elliot, to the Harajuku-esque Puma First Round Boot (pictured), to the punk-chic Converse Chuck Taylor Knee-High, to the celebrity-approved Nike x Riccardo Tisci, taking in a bewilderingly wide target audience across that spectrum.

Is this polarizing cross-pollination of footwear DNA an affront to fashion, or a bold and praiseworthy attempt to redraw traditional silhouettes that have remained unchanged for decades now? They’re certainly not for everyone; but then again, none of the best fashion is. Chanel even paraded a few pairs at their headline-grabbing "supermarket" show earlier this year. Just be careful what you wear them with, though, to avoid looking like Ultimate Warrior buying his groceries...

Nike Foamposite

This is a controversial one and we’re already braced for the backlash, but we’re going to say it: the Nike Foamposite is an ugly shoe. Then again, that’s exactly why we love it. The Foamposite is the ultimate collision between sci-fi futurism and sidewalk grandstanding, and every single inch of it screams “look at me.” When someone’s rocking Foams, it’s impossible not to sit up and take notice; they’re like a tractor beam for attention that works everywhere from the court to the curb, and you can’t help but respect their presence (and presumably that of the person wearing them). Their list of evangelists is too long to mention but when the NYPD has to shut down a product launch because a dangerous number of people are lined up outside the store to buy them, you know this is one line of sneakers that’s doing something right.

Reebok Instapump Fury

Far from wanting to badmouth something on its birthday (the Instapump Fury is celebrating 20 years in 2014), no one can deny this is one funky-looking piece of footwear. What makes the Fury unique in this list, however, is its sheer originality and endurance as a design. The signature zig-zag lines and gaping holes of the upper go against almost every established rule of what a modern sneaker should look like, yet they have remained unchanged since it first launched a full two decades ago. What now seems like a charming throwback to the bold style and crazy colors of the ’90s was, at the time, an incredibly forward-thinking piece of design, and while your average pair of Instapumps is enough to make today’s A.P.C.-loving minimalists weak at the stomach, it's their proud, unapologetic heritage that makes them such a beautiful, classic sneaker. Long may they continue.

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