Year: 2008
Listing Price: $6,005
Size: 12

Marshall Mathers, the mercurial rapper and sneakerhead, is the brain behind some of the rarest and most expensive sneakers in history. His “Encore” and “Carhartt” Jordan IVs are true sneaker unicorns. This featured listing is another ultra-rare Eminem collab, a pair of Jordan IIs paying homage to his hit song “The Way I Am.” Released in 2008 in conjunction with his autobiography of the same name, these Jordan IIs are covered in Em lyrics. Composed primarily in black, with a grey suede upper, red and white lettering, and his signature E logo on the tongue, they are a must for any Slim Shady fan. Only 313 pairs originally released, making this yet another incredibly rare pair from Detroit’s finest.

Year: 2006
Listing Price: $7,200
Size: 11

In August 2009, world-renowned DJ and avid sneakerhead Adam “DJ AM” Goldstein tragically passed away. Over the years, Goldstein had amassed an incredible selection of rare kicks and soon after his death, many were auctioned off on eBay with proceeds benefiting the DJ AM Memorial Fund. That’s where this rare pair of “Jordan Pack” Dunks came from. In 2006, Nike released a limited series of Dunk lows in Air Jordan inspired iterations, with this particular black/cement pair an homage to the iconic Jordan III. This pair alone warrants a space on the list, but knowing it was a part of AM’s personal collection (certificate of authenticity included), makes it an incredible piece of sneaker memorabilia. Respect to the legend.

Year: 2011
Listing Price: $5,500
Size: 8.5

Back in 2011, Nike linked up with sneaker magazine Sole Collector to release a limited edition of Penny Hardaway’s first signature shoe, the Air Foamposite One. Featuring co-branding on the heels, with a matte black upper and a royal blue tongue, this reimagined take still brings heavy old-school Orlando Magic vibes. Released among a slew of limited edition “Penny Packs,” which featured “Shooting Stars” and “Sharpie” foams–among other reimagined versions of classic Penny kicks–this was the rarest of the group and a must-grab for Penny fans, for which there are many.

Year: 2016
Listing Price: $1,000
Size: 8

Every time Comme Des Garçons and Nike get together, they push the boundaries of conventional sneaker design. Never has that been more true than their collaborative Dunk High. The first ever Comme des Garçons Homme Plus—the Japanese label's highest tier menswear line—Nike collaboration, the shows debuted during the Spring/Summer 2017 menswear show in June 2016, and were released later that fall. Exclusive to New York City's CdG Chelsea flagship and Dover Street Market, the shoes retailed for $320 and quickly sold out. Featuring completely clear side panels and toe boxes offset by black paneling and a teal highlight at the hell, the shoes marked an impressive foray into high-fashion sneaker collabs. These are a must for fanatical followers of the Japanese brand, especially with recent reports of a new clear Dunk Low slated to release in 2020.

Year: 2003
Listing Price: $2,111
Size: 9.5

This isn’t the first time NYC graffiti legend Futura has made his way onto our "Rarest Sneakers" list, considering anything he touches seems to turn into gold for Nike SB. This Dunk from 2003 is no different. In a relatively unassuming colorway, this dunk features tumbled nightshade leather on the toe box and heel, along with grey suede construction. Topped off with a white swoosh, this Futura dunk is an undisputed classic, and a rare find for SB die-hards and Futura fans alike. Add a signed box on top, and you've got yourself a winner.

Year: 2004
Listing Price: $1,500
Size: 12

Another classic SB Dunk, this “Homer” model from 2004 draws inspiration from the lazy patriarch of “The Simpsons.” Decked in the unchanging Homer Simpson color scheme of white leather, blue suede and a yellow suede swoosh, this homage to one of television’s most iconic characters was a home run. If you look closely at the insole, you’ll even see an illustration of the Cyclops, a callback to the story of Odysseus and the Cyclops from The Odyssey, which was written by the famous Greek poet Homer. Tremendous detail on a rare shoe, whether you’re a fan of the poet or the cartoon character (or both).

Year: 2018
Listing Price: $1,400
Size: 11.5

In 2018 Jordan Brand linked up with Miami-based sneaker boutique Solefly for a limited release of a collaborative Jordan I just in time for Art Basel Miami. The sneaker, a perfect homage to the 305, sports a dark green, white and orange colorway, made famous by the University of Miami. As if it wasn’t Miami enough, there are custom “MIA” and “305” branding on the tag inside the tongue. The shoe’s original release was shut down by police and very limited numbers eventually hit the market. There are very few of these available on Grailed and are an absolute must for any fan of “The U.”

Year: 2006
Listing Price: $1,195
Size: 10

This furry Dunk High from 2006 was the third installment of Nike SB’s beloved “Three Bears” pack in conjunction with Medicom Bearbrick. Referred to as the “Papa Bear,” the high top features blue suede and brown fur all over. Offset by a red swoosh, this pair was the capstone to a now ioncic collaboration . While the “Baby Bear” Dunk Low (previously featured) may be the rarest of the trio, the “Papa Bear” fetches a fair return on the open market as well. You just don’t see many of these available on Grailed.

Year: 2009
Listing Price: $300
Size: 9

With an October 29th retro release of the LeBron VII “Red Carpet” rapidly approaching, now is the perfect time to highlight arguably the greatest LeBron signature sneaker ever released. Originally worn during the 2009 season, these feature black woven paneling, white tumbled leather and a gorgeous teal accent color on the full-length Air unit and swoosh. It remains one of the most sought after colorways of any LeBron ever–hence the ensuing retro. This month’s release is sure to cause chaos, so grab a pair of the OG’s while you still can.

Year: 2019
Listing Price: $780
Size: 9.5

Aside from being one of the most important hoops sneakers of all time, the Air Jordan 1 was a hit among skaters since its debut. It’s no surprise then that Nike SB collaborated with Jordan Brand to release its own version of the iconic Jordan 1, including this popular “LA to Chicago” model. Decked in a fused Chicago Bulls black and white and Los Angeles Lakers purple and gold, this colorway is an ode to the 1991 NBA Finals, when MJ and the Bulls took down the Lakers to secure his first NBA Championship. Reimagining Jordan Is alongside Nike SB has proven to be a lucrative business strategy, as both these and the UNC-inspired Air Jordan I lows from this summer can attest. Despite the Jordan I overload in recent years, these remain a rare original take on a classic. Snag them now before the price goes up.