These are perhaps the coolest sneakers of all time. Chuck Taylors have never gone out of style. They transcend all social groups and clichés, everyone can wear this sneaker, and they will always be cool, even on you, Dad.
Converse Chuck Taylor All Stars. $50, converse.com.
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New Balance makes probably one of the most comfortable shoes ever.
This sneaker channels a Volvo-driving professor who lives in Vermont,
but at some point, somewhere, some hipster took that idea and made it
cool, and at the same time solidified this sneaker as one of the best
ever. J Crew realized that and now sells it in a variety of color
combinations. New Balance for J.Crew 1400 sneakers. $130, jcrew.com.
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Another Vanity Fair staffer—and I am not one to name names, but it’s Bramble Trionfo—said, “this sneaker was a real panty dropper.” I couldn’t have said it better. Every cute boy in high school had the Adidas Samba, and they literally wore them till they fell off their feet, not that I was paying attention. I totes had them myself, just so you know. What’s my number? Just tweet me.
Adidas Samba. $65, at Eastbay.
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Named after the famous tennis players, the Rod Laver and the Stan
Smith were introduced in 1970 and 1971, respectively. I put these in the
same category in order to include the shell toe (see slide nine). Yes, I
cheated—I chose 11 sneakers! Like the Converse All-Star, these are two
of the most iconic and copied sneakers of all time. Everyone should own a
pair.Adidas Rod Laver and Adidas Stan Smith. $65 and $60, shopadidas.com.
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Come on! In 1983, the Ex-O-Fit quickly made Reebok a household name. As everyone was learning how to jazzercise and do aerobics, this sneaker was with them through it all. I had them in four different colors—pretty neat, huh?
Reebok Ex-O-Fit. $110, at Crooked Tongues.
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These sneakers were so cool that a famous graffiti artist turned them into the AT-AT walker from Empire Strikes Back. I know, it’s super geeky that I know what an AT-AT Walker is, but it’s super cool that I own a shell-toe version of one. It is also the sneaker choice of Jay Z, so there.
The Adidas Superstar.