Fashion stylist Rachel Besser‘s been an avid sneakerhead since high school, when her self-described “love affair” with super-cool trainers began. “I realized that I could wear dresses with hard-to-find sneakers instead of heels and people would be like, ‘Damn! You have those?!’” she recalls. “Sneakers allowed me to feel confident while dressing comfortably when I was out with my friends.” Over the years, she’s cataloged a canon of classic kicks she considers to be the most iconic pairs ever made—some of her earliest scores were so precious, she didn’t even wear them.
“I vividly remember getting my first pair of Air Max ’97s—after I hunted them down. I loved them so much that I left them in the box because I was scared I’d ruin them,” she admits. “I didn’t wear them out for so long; that was ridiculous! I don’t buy sneakers for resale, so I should’ve just worn them the day I bought them.”
Now, she rocks her covetable new additions ASAP. “You never know when the love will fade, so I wear my sneakers when I’m in the honeymoon phase,” she says. And hey, who can really blame her? It seems like every week a different buzzy sneaker—or fresh twist on a beloved OG style—hits the market. Some tout technological advancements, like the Nike Air VaporMax and its entirely air-pocketed sole. Others are comebacks, such as the Adidas Superstar and Stan Smith, first released in 1969 and 1971, respectively. And while the stylist keeps up with all the current footwear fashions, she says there’s a half-dozen pairs that’ll always hold a special place in her heart—and closet.
Scroll down to see Besser’s short list of the 6 most iconic sneakers.
“The Air Max ’97 is happening right now in a big way!” says Besser. “I have to admit, I was kind of sad when Nike re-released the style this year—part of the reason for my deep love of the Nike’s Air Max ’97 is that they were so hard to get just a year ago, it made having a pair feel really special—but at the same time, I’m happy people get to enjoy these rad sneaks.”
“I know Stan Smiths and Superstars have gotten a lot of action in the past few years, but I’ve always liked the black Adidas Samba—it’s a low-key sneaker,” reveals the stylist.
“The Asics Gel-Kayano, in its many iterations, accomplishes the ‘Would my grandpa wear these?’ look,” says Besser. “The answer? Yes, he would, because these are so damn comfy!”
“People sleep on Prada’s America’s Cup,” the sneakerhead believes. “While classics are often styles from big sneaker brands, like Nike and Adidas, I think this is an unexpected [design] that makes the cut.”
“While sneaker trends ebb and flow, these iconic kicks [will] never go out of style,” Besser predicts.
“It’s a hilarious shoe, and I love how coveted it was when it was first released,” reveals the stylist. (The sneaker is strictly resale only at this point.) “If I saw anyone in a dope outfit wearing these, they’d have my respect.”
For more contemporary kicks worth adding to your collection, check out the styles celebs are rocking these days. Plus, get a glimpse inside the “Disneyland for sneaker designers.”