Year: 1985
Listing Price: $6,600
Size: 11.5

When the Jordan I originally released in 1985, no one knew that almost 35 years later, it would remain one of the most impactful shoes on the market. Originals from 1985 are on the sneakerhead Mount Rushmore, with pairs of Chicagos and Breds popping up more routinely on Grailed these days. These original Black Toes, however, are a rare unicorn (as are these 1985 Carolina Blue Jordan Is) complete with original Nike Air branding and the wear and tear that can only come from 35 years of history. This is a true holy grail for sneakerheads everywhere.

Editor's Note: Since the time of publication, the original listing has been deleted.

Year: 2002
Listing Price: $750
Size: 10.5

When Nike and Supreme first joined forces in 2002 to collaborate on a sneaker, Supreme chose the Nike SB Dunk Low. The rest, of course, is history, but the original Supreme Dunks from 2002 are still a very elusive grail for many collectors. There are many more 2003 Supreme Dunk Highs, as well as the re-released 2012 Dunk Lows in other colors available for resale, but this is one of the few (if only) 2002 version available on Grailed as of today. They are said to rarely hit the market, so now is a great opportunity to cross a grail off your list.

Year: 2007
Listing Price: $2,880
Size: 8

Some of the most sought-after sneakers on the resale market are Nike SBs from the 2000s, but this right here is if all those models formed like Voltron to create one crazy piece of hypebeast lore. 2007’s Nike What The Dunk Low took design cues from some of Nike’s most iconic SB releases, including the “Pigeon,” “Buck,” and “Lucky” Dunks to create one aesthetically captivating piece of sneaker history, and this is one of a handful currently available on Grailed (There are, however, a handful of the 2017 Highs designed by Thomas Campbell available).

Year: 2009
Listing Price: $2,335
Size: 12.5

The Nike Air Yeezy turned the sneaker world on its head back in 2009. Kanye West was arguably the biggest rapper in the game and these trailblazing kicks would lay the groundwork for his illustrious career as a sneaker designer. This pair in the “Zen Grey” colorway is listed as a promo sample and is in remarkably good shape compared to some other listings. The Air Yeezys find their way onto Grailed from time to time, but they are far more rare than the current brand of Yeezy’s adidas offerings. This was the one that started it all.

Year: 2006
Listing Price: $850
Size: 9.5

If the original 2002 Nike Supreme Dunk Low is the most scarce sneaker from Nike and Supreme collaborations, then 2006’s Supreme Blazer is not far behind. In a lush red leather, complete with Gucci-flavored accents and a faux-snakeskin swoosh, this sneaker is hypebeast heaven. There are only a handful of these floating around on Grailed, and with prices at a relatively modest price point compared to this model’s competition.

Year: 2009
Listing Price: $9,000
Size: 10.5

It’s only right that the Louis Vuitton Don himself, Kanye West, was given the opportunity to collaborate with the seminal fashion house back in 2009. His creation was a luxurious low-top sneaker that was equal parts detailed and ostentatious, much like its namesake. This patchwork colorway is the from a long dead Louis Vuitton footwear partnership, and, as such, are deadstock. This sneaker in this condition is a certified piece of Yeezy history.

Year: 2010
Listing Price: $4,800
Size: 9

This was the final release from Patta and Nike’s five sneaker collaboration spanning from 2009 to 2010, celebrating Patta’s five-year anniversary. The Cherrywood Air Max was its coup de grâce, an incredible sneaker designed by Dutch artist Parra in a decadent burgundy suede. Only 258 were released—hence the hefty price tag.

Year: 2016
Listing Price: 60,750
Size: 11

This sneaker was mere mythology for many years before Nike churned out a limited number of the TInker Hatfield-designed, Back to the Future-inspired Nike Air MAG back in 2011. The futuristic footwear is an homage to Marty McFly, the character who donned these back in the 1989 film. In 2011 only 1,500 were available via eBay auctions, with proceeds benefiting the Michael J. Fox Foundation for Parkinson’s disease research. For clarity, this sneaker is from the 2016 release, which unlike the 2011 edition, does feature the auto-lacing functionality made famous in the original movie. These sneakers were even rarer, with 89 pairs released to the public via raffle, only coming in sizes 7, 9, 11 and 13.

Year: 2017
Listing Price: $10,500
Size: 8.5

The Pharrell x Chanel adidas Human Race NMD is a unique beast. Part of Pharrell’s larger collab with adidas on the Human Race NMD model, the injection of famed fashion house Chanel (with whom Pharrell is now formally collaborating with on a capsule collection) made this iteration exceedingly special. Limited to 500 pairs, this collab was auctioned off at the now-defunct Colette store in Paris, going for €1,000 a pair. The combination of luxury maison prestige with sheer rarity makes these easily one of the most prized Pharrell-adjacent sneakers.

Year: 1986
Price: $1,349
Size: 10.5

The list has officially come full circle, with a second original Jordan I from 1986. This “Metallic Red colorway” is another lesser-known OG version. Predictably, this also means it receives less love than the “Chicagos” and “Breds” (and even less than the aforementioned Black Toe), but tracking down an original pair is a difficult task. It’s about time this iteration got the respect it deserves