15 Coolest Looking Sneakers of All Time

For young people who can't spend thousands on cars, the status symbol is shoes. Instead of listening to the Beach Boys sing about daddy's T-Bird, we hear rappers flaunting their Jordans. If you want to be cool, you've gotta rock the right kicks. But there's so many options, how can you be sure you're wearing something cool? Well, take it from me, you can't go wrong with any of the shoes on this list.

Nike Roshe Run

This shoe dropped pretty recently, but it’s quickly becoming a classic. It’s got the slimmed-down look that’s so popular right now, and a pleasantly simple sole. It’s also crazy comfortable. With sick new colorways coming out almost every week, it looks like people are going to be wearing Roshes for a long time.

Nike Dunk Hi

A classic shoe that just keeps on being great. Inspired by Michael Jordan’s first basketball shoe, the Dunk was actually designed for skateboarding. That doesn’t mean only skaters wear it, though. Nike’s been pumping out sick limited-edition colorways for years, guaranteeing that sneakerheads will drool over Dunks for years to come.

Nike Stephan Janoski

Another newcomer, this shoe started out by revolutionizing skateboarding with its sleek, boat shoe meets sneaker design. Then it got picked up by mainstream culture and became even more popular. Similar to the Roshe, this shoe is simple but bold, and the fact it’s on the cheaper side doesn’t hurt either. Janoskis are here to stay.

Supra Ellington

A less well-known shoe than the others on this list, the Supra Ellington has been lurking beneath the surface for a while. Supras always strike an impressive balance between pure skate shoes and fashionable sneakers, and the Ellington is no different. It looks dope, and if you want to bust out a kickflip, it’ll work for that too.

Supra Skytop III

The Skytop I and Skytop II were ugly shoes. They had a certain place in the hearts of people who enjoy wearing sneakers that reach up higher than their mid-calf socks, but for most people the shoes were just too intimidating. Not the III’s though. This shoe trimmed the top and redesigned the toe cap, turning a somewhat dated model into a sexy piece of modern footwear.

Reebok Instapump Fury

This should be an ugly shoe. It’s complicated, the laces are hidden by a giant (and ultimately useless) air pump, and the sole is broken into two pieces like some kind of weird runway model high heel. And yet somehow Reebok jammed all this ugly together and made something cool. I don’t get it, but I’d still get it, if you know what I mean.

Nike Air Huarache

Another shoe that could be ugly but ends up looking dope, the Air Huarache not only checks out in the style department, but it also feels good to wear. In addition to a luxurious padded sole, this shoe has got elastic woven throughout its upper portions. This means your foot feels like it’s getting a hug the whole time you’re wearing these shoes, which is pretty sweet.

Vans Sk8 Hi

Classic skater, classic style. This shoe started out as a staple of every skate punk’s wardrobe, but more fashion-minded designers quickly started using it as a canvas for their shoe art. Now there are a ton of sick colorways and the shoe adds a subtle but eye-catching bohemian flair to any outfit.

Huf Classic Hi

Sort of a combination between the Sk8 Hi and old Chuck Taylor’s, the Huf Classic is a new shoe that’s making a big splash. The rubber creeping onto the heel and toe cap are an especially interesting detail, and the smooth suede upper is pure style.

Huf Dylan

Dylan Reider’s shoe for Huf was accompanied by a pretentiously artsy ad that set off debates in the skate community, but no one has any complaints about the shoe itself. It’s cleverly functional, working in foot protection while maintaining a handsome, well-groomed look. I don’t think it’ll be long before the Dylan is a staple in any fashion-conscious shoe collection.

Vans Chima Ferguson

In a world of complex stitching and eye-popping colorways, a purely simple shoe can be nice. That’s where the Chima comes in. This shoe isn’t remarkable in any way, which is part of it’s appeal. It’s smooth, solid footwear, and every wardrobe needs some of that.

Adidas ZX Flux

One of the most awesomely subtle shoes I’ve ever seen from Adidas, the ZX Flux just looks like a fun shoe. The breathable mesh upper is smooth, the shape is beautiful, and the stripped-down logo just ties it all together perfectly.

Adidas Stan Smith

This shoe is great not only because it looks sweet, but also because the backstory is interesing. Stan Smith is a tennis player who was sponsored by Adidas. But this shoe is actually designed to be a skate shoe. To accompany the shoe’s release, Adidas put out a hilarious mock interview with Stan in which he claimed skateboarding, not tennis, is his true passion. The awesomeness of that ad campaign would get this shoe on the list no matter what, but the fact this shoe also looks amazing certainly doesn’t hurt.

Converse Chuck Taylor All Star

A classic. You haven’t lived until you’ve owned a pair of Chuck Taylors.

Nike Flyknit Chukka

This shoe is basically a sock with a sole. I shouldn’t need to say more about how great it is, but in case that didn’t convince you, the Flyknit Chukka also looks amazing. The fact it’s made out of thousands of fibers allows Nike to decorate this shoe with some of the most innovative colorways ever seen, and its thin sole and low profile make it perfect for adding a little footsy flair to an outfit.