Start Investing

The Most Expensive Sneakers of All Time

Photo by Ryan Kobane

The Most Expensive Sneakers of All Time
Anna Millard

From athletes to rappers, many of culture’s MVPs are self-described sneakerheads. As society puts increasing demand on the style of shoes once used only for sports, kicks are taking their place as fashion royalty. In response, the value of sneakers is finally catching up to athlete’s jerseys—the king of sports memorabilia which routinely go for multiple millions of dollars. Take a look at the history of world record holders for most expensive sneakers. 

1. “Grammy Worn” Nike Air Yeezy 1 Prototype - $1.8 million




Source: Sotheby’s


2021 was an unprecedented year across the board, including a sneaker sale that shattered records and changed the way shoes are auctioned for good. The “Grammy Worn” Nike Air Yeezy 1 Prototypes were worn by Ye at the 50th Grammys when the controversial rapper performed hit songs “Hey Momma” and “Stronger”. 


The pair was the debut design of the Yeezy collection, introducing the world to Kanye as a fashion mogul. The black leather hightops with signature pink Y design were sold to the investment platform Rares in a April 2021 private sale, more than tripling the former record for sneaker sales of only (only!) $615,000. 



2. Michael Jordan ‘Shattered Backboard’ Air Jordan 1 - $615,000



Source: Christie’s


Global giant auction house Christie’s passed their first ever sneaker auction in August of 2020 with flying colors when they sold a game worn pair of first edition Air Jordans signed by MJ himself for $615,000. The shoes hold a special place in basketball culture, worn during a famous 1985 exhibition match when Jordan dunked so hard that the backboard shattered into thousands of tiny glass pieces. As a special bonus for the buyer (something you would not be excited about if you intended to wear the shoe), one of those pieces is still lodged in the left sole.


The Shattered Backboard Jordan 1s are currently trading on Otis.



3. Michael Jordan “Game Worn” 1985 Air Jordan 1 - $560,000


Source: Sotheby’s


Next up is a pair of first edition Air Jordans, also worn and signed by the namesake basketball legend. The player sample size 13-13.5s (or "TYPS" specifications) were sold by Sothebys in 2020 for an outstanding $560,000. 


The kicks feature the iconic “Chicago” colorway, reflecting the red and black colors of the Chicago Bulls—the team Jordan led to 6 NBA championships over 13 seasons before taking a hiatus from the sport to try his hand at baseball. Though Jordan is long retired, Nike’s popular shoe line is going strong with 34 editions and counting.  

A signed, deadstock pair of first edition Air Jordans with "TYPS" specifications is currently trading on Otis.


4. Nike Waffle Racing Flat “Moon Shoe” - $437,500


Source: Sotheby’s


While other kicks on this list are valuable for the famous feet who wore them, this never-worn piece of sneaker history is important for the hands who made them. The Nike Waffle Racing Flat was designed in 1972 by Nike co-founder Bill Bowerman and one of 12 pairs ever hand-cobbled by Geoff Holliste, one of Nike’s first employees. 


The sneakers were dubbed “Moon Shoes” because the waffle sole (which co-founder Bill Knight claims in his best-selling book was inspired by Bowerman’s wife’s waffle iron) left similar prints in dirt to the prints of astronauts on the moon. 


Far fewer than the original 12 remain today and this pair is the only unworn pair in known existence. Sotheby’s sold the iconic shoes in 2019 for $437,500 in the auction house’s first-ever foray into collectible sneakers. 



5. Michael Jordan “Game Worn” Converse Fastbreak - $190,373

Source: SCP Auctions


The first non-Nike to make the list, SCP Auctions sold this signed pair of Converse Fastbreaks worn by MJ at the Olympics during the gold-medal game against Spain for what was at the time a world-record price of $190,373. 


Jordan had no say in the design of this pair, showing how in-demand the market for the bball legend’s foot sweat really is. But there is a lot of history stored in these soles—in addition to winning gold for the U.S., this was 21-year-old Jordan’s last amatuer game before going pro, and was the last time MJ was ever seen wearing a non-Nike pair.



6. Michael Jordan “Flu Game” 1997 Air Jordan XII - $104,765

Source: Grey Flannel Auctions


Game 5 of the 1997 NBA finals became known to sports fans as the “flu game” because Jordan led the Bulls to victory despite being visibly ill with a flu rumored to be caused by poisonous pizza. After the highly publicized victory, MJ signed his 1997 Air Jordan XIIs before giving them to teenage ball boy Preston Truman. About 30 years later, Truman entrusted them to Grey Flannel Auctions who garnered $104,765 for the Nikes.



7. Honorable Mention: Drake’s Solid Gold OVO x Air Jordan - +$2 million


If you’re wondering why the most expensive pair is at the bottom of the list, let’s set the record straight: no one (except champagne papi himself) knows the exact details on these. But the novelty is too good to skip over. 


Supposedly, Drake commissioned a solid gold pair of Nike Air Jordans from artist Matthew Senna in the style of the singer’s actual line with Nike, Ovo X Air Jordan. Unlike the real-deal editions which could cost a collector $600, GQ did the math and estimates the Canadian crooner must have shelled out at 1.9 million for materials alone to make the sneaks out of solid gold. Unlike the others, these have never been certified by an auction house, so all we really have to go on is Drake’s word and instagram pics.

**

Otis has several sneakers available for investment and is dropping a new pair of sneakers: the Jordan 1 Metallic Red, on Tuesday, September 14th at 12pm ET.

OTIS WEALTH, INC. (“OTIS”) OPERATES THE WITHOTIS.COM WEBSITE (THE “SITE”) AND A MOBILE APP-BASED PLATFORM (THE “APP”), AND IS NOT A BROKER-DEALER OR INVESTMENT ADVISER. ALL SECURITIES-RELATED ACTIVITY IS CONDUCTED BY DALMORE GROUP, LLC (“DALMORE”), A REGISTERED BROKER-DEALER AND MEMBER OF FINRA (WWW.FINRA.ORG) AND SIPC (WWW.SIPC.ORG), LOCATED AT 525 GREEN PLACE, WOODMERE, NY 11598. YOU CAN REVIEW THE BROKERCHECK FOR DALMORE HERE. AN UP-TO-DATE DALMORE FORM CRS IS AVAILABLE HERE.

YOU SHOULD SPEAK WITH YOUR FINANCIAL ADVISOR, ACCOUNTANT AND/OR ATTORNEY WHEN EVALUATING ANY OFFERING. NEITHER OTIS, ITS AFFILIATED ISSUERS NOR DALMORE MAKES ANY RECOMMENDATIONS OR PROVIDES ADVICE ABOUT INVESTMENTS. THE SITE AND THE APP MAY MAKE FORWARD-LOOKING STATEMENTS. YOU SHOULD NOT RELY ON THESE STATEMENTS BUT SHOULD CAREFULLY EVALUATE THE OFFERING MATERIALS IN ASSESSING ANY INVESTMENT OPPORTUNITY, INCLUDING THE COMPLETE SET OF RISK FACTORS THAT ARE PROVIDED FOR YOUR CONSIDERATION.

OTIS GALLERY LLC (“GALLERY”) AND OTIS COLLECTION LLC (“COLLECTION”) ARE CONDUCTING PUBLIC OFFERINGS PURSUANT TO REGULATION A AND PRIVATE OFFERINGS PURSUANT TO REGULATION D UNDER THE SECURITIES ACT OF 1933, AS AMENDED, THROUGH THE APP. THE OFFERING CIRCULAR FOR GALLERY CAN BE FOUND HERE, AND THE OFFERING CIRCULAR FOR COLLECTION CAN BE FOUND HERE. THE PRIVATE PLACEMENT MEMORANDUM FOR ANY OFFERING CONDUCTED PURSUANT TO REGULATION D HAS BEEN OR WILL BE, AS APPLICABLE, DISTRIBUTED DIRECTLY TO INVESTORS. PAST PERFORMANCE IS NO GUARANTEE OF FUTURE RESULTS. INVESTMENTS SUCH AS THOSE ON THE OTIS PLATFORM ARE SPECULATIVE AND INVOLVE SUBSTANTIAL RISKS TO CONSIDER BEFORE INVESTING, OUTLINED IN THE RESPECTIVE OFFERING MATERIALS AND INCLUDING, BUT NOT LIMITED TO, ILLIQUIDITY, LACK OF DIVERSIFICATION AND COMPLETE LOSS OF CAPITAL. KEY RISKS INCLUDE, BUT ARE NOT LIMITED TO, LIMITED OPERATING HISTORY, LIMITED DIVERSIFICATION, RISK OF ASSET DAMAGE OR THEFT AND LACK OF VOTING RIGHTS. ALSO, THE ADVERSE ECONOMIC EFFECTS OF THE COVID-19 PANDEMIC ARE UNKNOWN AND COULD MATERIALLY IMPACT THIS INVESTMENT. AN INVESTMENT IN AN OFFERING CONSTITUTES ONLY AN INVESTMENT IN A PARTICULAR SERIES AND NOT IN OTIS, GALLERY, COLLECTION OR THE UNDERLYING ASSET(S). INVESTORS SHOULD CAREFULLY REVIEW THE RISKS LOCATED IN THE RESPECTIVE OFFERING MATERIALS FOR A MORE COMPREHENSIVE DISCUSSION OF RISK.

INVESTMENT OVERVIEWS CONTAINED HEREIN CONTAIN SUMMARIES OF THE PURPOSE AND THE PRINCIPAL BUSINESS TERMS OF THE INVESTMENT OPPORTUNITIES. SUCH SUMMARIES ARE INTENDED FOR INFORMATIONAL PURPOSES ONLY AND DO NOT PURPORT TO BE COMPLETE, AND EACH IS QUALIFIED IN ITS ENTIRETY BY REFERENCE TO THE MORE-DETAILED DISCUSSIONS CONTAINED IN THE RESPECTIVE OFFERING CIRCULAR FILED WITH THE SECURITIES AND EXCHANGE COMMISSION (“SEC”) OR OTHER OFFERING MATERIALS RELATING TO SUCH INVESTMENT OPPORTUNITY.

FROM TIME TO TIME, AFFILIATES OF OTIS WILL SEEK TO QUALIFY ADDITIONAL SECURITIES UNDER REGULATION A. FOR OFFERINGS THAT HAVE NOT YET BEEN QUALIFIED, NO MONEY OR OTHER CONSIDERATION IS BEING SOLICITED AND, IF SENT IN RESPONSE, WILL NOT BE ACCEPTED. NO OFFER TO BUY SECURITIES CAN BE ACCEPTED, AND NO PART OF THE PURCHASE PRICE CAN BE RECEIVED, UNTIL AN OFFERING STATEMENT FILED WITH THE SEC HAS BEEN QUALIFIED BY THE SEC OR UNLESS AS STATED IN THE OFFERING MATERIALS RELATING TO AN INVESTMENT OPPORTUNITY, AS APPLICABLE. ANY SUCH OFFER MAY BE WITHDRAWN OR REVOKED, WITHOUT OBLIGATION OR COMMITMENT OF ANY KIND, AT ANY TIME BEFORE NOTICE OF ACCEPTANCE GIVEN AFTER THE DATE OF QUALIFICATION BY THE SEC OR AS STATED IN THE OFFERING MATERIALS RELATING TO AN INVESTMENT OPPORTUNITY, AS APPLICABLE. AN INDICATION OF INTEREST INVOLVES NO OBLIGATION OR COMMITMENT OF ANY KIND.

OTIS DOES NOT OFFER REFUNDS AFTER AN INVESTMENT HAS BEEN MADE. PLEASE REVIEW THE RELEVANT OFFERING MATERIALS AND SUBSCRIPTION DOCUMENTATION FOR MORE INFORMATION.

AN ACTIVE TRADING MARKET FOR ANY SERIES OF GALLERY OR COLLECTION INTERESTS MAY NOT DEVELOP OR BE SUSTAINED. IF AN ACTIVE PUBLIC TRADING MARKET FOR GALLERY OR COLLECTION INTERESTS DOES NOT DEVELOP OR IS NOT SUSTAINED, IT MAY BE DIFFICULT OR IMPOSSIBLE FOR YOU TO RESELL YOUR INTERESTS AT ANY PRICE. EVEN IF AN ACTIVE MARKET DOES DEVELOP, THE MARKET PRICE COULD DECLINE BELOW THE AMOUNT YOU PAID FOR YOUR INTERESTS. THERE IS NO ASSURANCE THAT THE OTIS PLATFORM WILL PROVIDE AN ACTIVE MARKET FOR RESALES OF GALLERY OR COLLECTION INTERESTS. FURTHER, WITHOUT THE OTIS PLATFORM, IT MAY BE DIFFICULT OR IMPOSSIBLE FOR YOU TO DISPOSE OF YOUR INTERESTS. IF THE MARKET DEVELOPS FOR ANY SERIES OF GALLERY AND/OR OTIS COLLECTION INTERESTS, THE MARKET PRICE OF SUCH INTERESTS COULD FLUCTUATE SIGNIFICANTLY FOR MANY REASONS, INCLUDING REASONS UNRELATED TO PERFORMANCE, THE UNDERLYING ASSETS OR ANY SERIES, SUCH AS REPORTS BY INDUSTRY ANALYSTS, INVESTOR PERCEPTIONS OR ANNOUNCEMENTS BY COMPETITORS REGARDING THEIR OWN PERFORMANCE, AS WELL AS GENERAL ECONOMIC AND INDUSTRY CONDITIONS.