7 Vintage (And Collectible) Sneakers Worth a Pretty Penny

In the world of sneakers and status, building a curated collection is a big deal that can spell big bucks when you can get your hands on the right shoes. Some sneakerheads devote their lives to tracking down the latest must-have pair, opting to turn the leather, canvas, and glue holding these shoes together into a way to make extra money on the side by flipping the more high-end sneakers.

Whether you're a seasoned collector with shelves of tennis shoes in display cases or just a curious onlooker, take a look at some of the shoes fetching a pretty penny and learn what makes them such a big deal in the world of vintage shoe collectors.

Editor's note: All current values are pulled from StockX unless otherwise noted, and prices are subject to change depending on shoe size. 

Estimated Value: Up to $12,000

Born of a collaboration between Nike and streetwear brand Cactus Plant Flea Market, the Dunk Low sneaker caught the eye of sneaker seekers thanks to the Swarovski crystals covering the shoe. 

In addition to the added bling, the sneakers are designed with an oversized Swoosh, extra tongue padding, and double lace flaps, which means they'll be comfortable to wear… if you ever take them out of the display box, that is.

These shoes were released in early November 2020, and they sold for $550 a pop, according to myGemma. Today, in-the-know sneaker aficionados say the pair's worth upwards of $12,000.

Estimated Value: Up to $36,393​

The "Red October" was Kanye West's final collaboration with Nike before switching over to its rival, Adidas. Kanye debuted the sneakers during a May 2013 performance on Saturday Night Live, putting them on the radar of fans everywhere.

Unfortunately for fans, the sneakers sold out immediately after a surprise release, according to myGEMMA, and now you can't get your hands on a pair without dropping tens of thousands of dollars.

Estimated Value: $40,000​

A collaboration between rapper Eminem, popular workwear brand Carhartt, and Jordan Brand resulted in a rugged yet stylish Air Jordan 4. This shoe was created as a friends and family exclusive, however, 10 brand-new pairs were auctioned off to the public.

If you want to snag a pair of Eminem-laced Nike history, be prepared to shell out upwards of $40,000 on StockX or to start your bidding at around $18,000 on eBay. 

Estimated Value: Up to $50,000​

Inspired by the self-lacing shoes from Back to the Future Part II, the Nike Air Mag was released in a limited run in 2011. With only 1,500 pairs ever made and proceeds going to charity, the BBC says that these futuristic sneakers are a philanthropist-collector's dream. Each pair sold for a staggering $4,000, but 14 years later, the Air Mags can command tens of thousands of dollars on auction blocks.

Perhaps even more shocking, the BBC reports that a pair of the original version of these sneakers worn by Michael J. Fox's Marty McFly sold for nearly $100,000 in 2018, highlighting the enduring popularity of this fictitious style. 

Estimated Value: Up to $50,000​

Part of Nike's "White Dunk" series, the "Paris" edition features artwork by French painter Bernard Buffet. With only about 200 pairs produced, each with a unique design, these sneakers are both rare and artistically significant, commanding huge price tags as a result.

In fact, Hypebeast reports that a pair of these once sold for $133,000. Depending on what size you're looking for, you can find these shoes on auction sites like eBay at prices that range from $1,000 to $325,000. 

Estimated Value: Up to $68,786

The Air Jordan 1 "Chicago" is a cultural artifact highlighting Nike's game-day sneaker style. An autographed, game-worn pair sold for $189,000 at a Christie's auction in 2020, according to the auction house, elevating the sneaker as a tangible piece of basketball and broader cultural history.

Considering the fact that Christie's puts the estimated value of these sneakers between $200,000-300,000, we don't think we've seen the last of these shoes.'

However, if you'd like to get your hands on a pair that weren't worn by the basketball great, you can find pairs in a variety of conditions online, including some used options on eBay that start around $1,000.

Estimated Value: Up to $13,975

75​Debuted during Kanye West's performance at the 2008 Grammy Awards, the Nike Air Yeezy 1 Prototype marked the official debut of Nike's Yeezy line.

Kanye's sneakers were so unique that even sneakerheads could not identify the type; the only clue to the shoe's provenance was its iconic swoosh, although there had been year-long rumors of a secret Kanye-Nike collaboration for the awards show.

The shoe's secrecy and hype helped rev up its sale price. The shoes fetched a record-breaking $1.8 million in a private sale, according to Hypebeast. 

Of course, you won't be able to land yourself a pair of the ones worn to the Grammys, but you may be able to get your hands on some of the Nike Air Yeezy 1 designs on auction sites, which all appear to start the bidding in the low thousands thanks to the rare nature of the shoe. 

The sneaker market has evolved from functional footwear for athletes to a niche hobby to a significant collectible investment. Rarity, mystique, and celebrity sweat all contribute mightily to a sneaker's worth.

And, while it's unlikely that you'll ever get the chance to purchase a limited-edition pair of sneakers worn by an up and coming star, if you do, there's clearly something to be said about how reselling these sneakers could boost your bank account in the long run.