British artist Debbie Wingham embarked on a series of “most expensive things” that included a multimillion-dollar dress, cake, accessories and, yes, shoes. In 2017, she unveiled a pair of heels valued at $15.1 million at the time. Made as a birthday present for an unnamed family, the shoes featured extremely rare large pink and blue diamonds, as well as four flawless three-carat white diamonds and 1,000 pointer diamonds. The hardware on the sandals was made from solid gold, and each stone has a platinum setting. What’s more, the leather upper was painted with 24-carat gold paint and sewn together with 18-carat gold thread.

American designer Stuart Weitzman created several “million-dollar sandals” during the 2000s, but his most expensive pair were the Rita Hayworth heels, worn by actress and singer Kathleen York on the Oscars red carpet in 2006. The sandals were decorated with a set of film legend Rita Hayworth’s earrings, which featured 200 rubies, 200 sapphires and 48 diamonds. The earrings were later returned to Hayworth’s daughter, Princess Yasmin Aga Khan, and Weitzman switched out the jewels on the shoe for Swarovski crystals.

These $2 million heels were a collaboration between Stuart Weitzman and Eddie Le Vian, CEO of the prestigious Le Vian Jewelry. The evening sandals were made with 185-carats of museum quality tanzanite and 28 carats of gem-quality natural diamonds set in 18 karat white gold. In 2007, the shoes won the Tanzanite Celebration of Life Jewelry Design Awards and the following year were spotted at a Le Vian party in Las Vegas. According to LinkedIn posts by Le Vian, the shoes can still be custom ordered from the jewerly house.

These sparkling stilettos by designer Stuart Weitzman debuted on the feet of singer Allison Krause at the 2004 Academy Awards, as part of his “Million-Dollar” shoes collection. Valued at $2 million at the time, the sandals were made with Italian leather and 565 Kwiat diamonds. The right shoe also had a rare 5-carat amaretto diamond that by itself was worth more than $1 million. On the Oscars red carpet, Krauss was accompanied by a security guard to ensure the safety of the shoes. She later received a replica of the heels with crystals instead of diamonds.

When it sold through a private transaction in 2021, this Nike Air Yeezy sample worn by Kanye West at the 2008 Grammys blew away the previous record-holder for most expensive pair of shoes (the previous $560,000 pair of Air Jordans). The shoe marked the first-ever public appearance for what was then West’s highly anticipated first Nike sneaker. Rares, a platform that allowed users to buy shares in sneakers just like stocks, bought the Air Yeezys before turning them into an IPO later in the year. In 2023, the company sold them for just $180,000 after declaring bankruptcy — and after West orchestrated his fall from grace.

American designer Stuart Weitzman created his own homage to the famed heels in “The Wizard of Oz,” giving the look a more delicate touch by way of barely-there straps and a sculpted stiletto. Made in collaboration with Oscar Heyman jewelers, the heels are outfitted with 642 Burma rubies weighing 123.33 carats, set in a half pound of platinum. Estimates at the time valued them at $1.2 million. Weitzman also constructed the heels using platinum thread. The size 4 ruby sandals (the same size Judy Garland wore) were originally created for the 2003 Academy Awards, but were never worn on the red carpet. They did, however, later take a world tour, going on display at the Baselworld watch and jewelry show, as well as other locations, including Harrods of London, where they were watched by armed guards.

Stuart Weitzman kicked off his “million-dollar shoes” collection in 2002, selecting actress Laura Harring from “Mulholland Drive” to wear his custom pair of Platinum Guild Stilettos to the Academy Awards ceremony. The heels, adorned with 464 diamonds, were evaluated at $1 million. (Harring, who was also wearing a $25 million diamond necklace, was accompanied on the red carpet by four bodyguards.) The designer released a more affordable version of the shoes worn by Harring 10 years later, swapping the diamonds for Swarovski crystals, lowering the price tag from $1 million to $595.

In 2008, Stuart Weitzman created his final — and most controversial — “million-dollar” shoe, the Retro Rose pumps. The T-strap heels featured a rose embellishment encrusted with Kwiat diamonds valued at $1 million. They were intended for writer and director Diablo Cody to wear to the Academy Awards (Cody was nominated for — and ended up winning — Best Original Screenplay for “June”). But she quite publicly refused to wear the shoes before the ceremony. “They’re using me to publicize their stupid shoes and nobody asked me,” Cody wrote on her MySpace, adding, “I would never consent to a lame publicity stunt at a time when I already want to hide.” Weitzman told AP at the time that he’d made the cost of the heels clear to Cody when he met with her and blamed her team for the lack of communication. “I’m just embarrassed that she wrote what she wrote,” he told AP. The following year, as the Great Recession continued to impact global economies, Weitzman told the New York Post he would stop creating million-dollar shoes for the event.

When actress Regina King stepped onto the red carpet at the 2005 Academy Awards (where she was recognized for her role in the film “Ray,”) she was wearing a very expensive piece of Hollywood history. King’s strappy stiletto sandals, made by American designer Stuart Weitzman, featured on the toe a ribboned flower accent. Within that was nestled a pair of diamond earrings that belonged to screen legend Marilyn Monroe. Weitzman reportedly had to pay a $1 million insurance policy to ship the earrings from the collector’s home to his workshop, and they were immediately returned after the event.

The final Air Jordan 1 on this list, this pair stands out for it utilizing the sole from the Nike Dunk rather than its original because the former is softer and wider. Having been signed and worn by Michael Jordan, the shoes were photo-matched to an April 1986 game against the Milwaukee Bucks after Jordan returned from breaking his foot.

In 2000, one of the four remaining pairs of ruby slippers worn by Judy Garland as Dorothy Gale in “The Wizard of Oz” sold at auction for $666,000. The shoes have a unique history. A Tennessee woman named Roberta Jeffries Bauman won the ruby slippers in 1940, after placing second in a movie trivia contest. She reportedly kept them in her closet until 1970, when she moved them to a bank security box after seeing another pair go for $15,000 in an MGM auction. Eventually, in 1988, Bauman signed a contract with Christie’s East, selling her pair for $165,000 to Anthony Landini. Landini then partnered with The Walt Disney Company to exhibit the shoes at Disney and MGM Studios’ Florida Theme Park in 1989. And in 2000, he sold the shoes to collector David Elkouby, who owned the former Starworld film memorabilia store in Los Angeles. In a 2020 interview with The Hollywood Reporter, Elkouby said he checks in on the footwear once a year at an L.A.-area bank vault.

Although this Air Jordan 1 has the original “Chicago” color scheme, it’s the very sneaker that later inspired the “Shattered Backboard” colorway. As the name suggests, Michael Jordan wore the pair when he shattered a backboard while dunking in a 1985 exhibition game in Trieste, Italy. There’s even a piece of glass embedded into the outsole of the shoe, which Jordan signed and gave to Gianni Bertolitti, captain of the opposing Stefanel Trieste team. When the orange, white and black Air Jordan 1 “Shattered Backboard” released in 2015, it took on the colors of Stefanel Trieste. The shoes sold for $615,000 in August 2020 as part of an auction orchestrated by sneaker consignment store Stadium Goods and luxury auction house Christie’s.

Here we have yet another game-worn Air Jordan 1 from Michael Jordan’s rookie year, but this pair was signed on two separate occasions as part of its unusual backstory. Jordan first signed the ankle of both shoes and gave them to teammate Gene Banks, who had just joined the Chicago Bulls from the San Antonio Spurs. Banks later gave the shoes to Spurs reporter Rick Lozano, who had them signed once again by Jordan upon interviewing him just before the 1991 game in which he clinched his first NBA title. On one of the toes, Jordan jotted “1st pair” along with the signature.

The list of most expensive shoes contains several pairs worn and signed by Michael Jordan, many of them marking notable moments from Jordan’s career or the evolution of his signature sneakers. This pair of Air Jordan 1s from the NBA icon’s 1985 season saw its price bolstered by the cultural zeitgeist when it went up for auction. Bidding for it closed in May 2020, just as the final episode of “The Last Dance” docuseries aired and when the pandemic was at a peak and there was very little else commanding anyone’s attention. Sotheby’s, which hosted the auction, reported that bidding spanned four continents, and 70 percent of the bidders were newcomers. At the time, it set a record as the most expensive pair of sneakers ever sold — a distinction that was quickly surpassed just months later.

These ruby slippers are another one of the four known pairs worn by Judy Garland in “The Wizard of Oz.” They gained even more star power in 2012, when actor Leonardo di Caprio led a group of donors (that also included director Steven Spielberg) to buy the shoes for $2 million for the Academy of Motion Picture Arts & Sciences. It’s believed that these were the shoes that Garland wore for closeups and insert shots, like those famous heel-clicks. Originally created by wardrobe designer Gilbert Adrian, the shoes languished in MGM storage for decades before finding their way into private collections, including that of costumer Kent Warner, one of the first people to understand the value of this piece of cinema history. The ruby slippers are now part of the permanent collection at the Academy’s museum in Los Angeles.

To mark the 50th anniversary of the 1939 classic film “The Wizard of Oz,” Harry Winston jewelers created a commemorative pair of ruby slippers valued at the time at $3 million. The size 4 heels boasted 2,329 rubies and diamonds on each shoe, with about 25 carats of diamonds and 1,500 carats of rubies. The grand unveiling took place at Trump Tower in Manhattan, with CEO Ron Winston on hand, along with Donald Trump and his then-wife Ivana Trump, according to the Los Angeles Times. Winston reportedly planned to gift the shoes to the Make-a-Wish Foundation for a charity auction.

Created by United Arab Emirates-based brand Jada Dubai in partnership with Passion Jewelers, the Passion Diamond Shoes went on display in September 2018 at the world’s only seven-star hotel, Burj Al Arab, in Dubai, United Arab Emirates. They were valued at $17 million at the time and reportedly took nearly nine months to produce, with the collaborating designers’ names inscribed in gold on the insoles. The soaring stilettos boast two 15-carat diamonds on the upper, adorned with hundreds more carats — all of them the exceptionally rare D flawless diamonds.

During the 2000s, American designer Stuart Weitzman famously created a series of “million-dollar” heels for the Academy Awards red carpet. While these Diamond Dream sandals, which were worn by “Dreamgirls” actress Anika Noni Rose at the 2007 Oscars, fell short of the title with a value of $500,000, they still earn a place on the list of the most expensive shoes in the world. The silver stiletto sandals were adorned with 1,420 individual brilliant-cut Kwiat diamonds, weighing over 30 carats, with the diamonds set in platinum circles.

The “Flu Game” was one of the most iconic moments of Michael Jordan’s career. Battling illness — or food poisoning brought on by a suspicious pizza, if you believe the man himself — Jordan managed to score 38 points, including 15 in the fourth quarter and a go-ahead three-pointer with 25 seconds remaining, while winning game five of the 1997 finals. Utah Jazz ball boy Preston Truman received the signed shoes following the heroic performance from Jordan, who rewarded him for having supplied his favorite post-game snack of applesauce for the past two seasons.

Contrary to the sneaker legend, the Air Jordan 1 was never actually banned by the NBA. That denigration-turned-honor belonged to the Air Ship, a similar silhouette worn by Michael Jordan until he received his first signature sneaker. This particular pair was worn by Jordan in the fifth game of his rookie season and is the earliest known pair from his NBA career. He signed them and gave them to Tommie Tim III Lewis, the Denver Nuggets ball boy who later included his staff pass from the season for the auction. While the Air Ships commanded a mighty fee in 2021, the shoes sold again in 2023 for only $624,000.

The most valuable sneaker in the world is the Air Jordan 13 “Bred” that Michael Jordan wore during Game 2 of the 1998 NBA Finals, his final championship run that was dubbed his “Last Dance.” Jordan signed them and gave them to another ball boy who had successfully tracked down his lost jacket. The shoes were sold by Sotheby’s in April 2023. The auction house said at the time, “The historic sneakers were worn during the most recognizable season of Jordan’s storied career, which helped secure his legacy as the greatest basketball player of all time.” No pair has gone on sale from later in that final championship series.

In 2016, rapper Drake shared on Instagram a look at his latest acquisition: a one-of-one pair of solid-gold OVO x Air Jordan 10s customized by conceptual artist Matt Senna. Made with 24-carat gold, the shoes were estimated to be worth about $1.9 million based on the going rates of gold at the time. But don’t ever expect to see Drake hitting the stage or court in them. Senna confirmed to The Hollywood Reporter that the sneakers are works of art and are not meant to be worn.

TV host and mega shoe collector Nick Cannon commissioned this pair of diamond-encrusted Tom Ford smoking slippers to wear on the 2014 season finale of “America’s Got Talent.” The shoes were embellished by L.A.-based jeweler Jason of Beverly Hills using more than 14,000 full-cut round diamonds placed in white gold atop a Tom Ford sole. The pair has a total weight of 340 carats and reportedly took more than 2,000 hours of labor to complete. Cannon announced later in 2014 that he would donate the shoes to St. Mary’s Hospital for Children in Queens, N.Y., for charity fundraising, however they were still in his possession when Complex visited his closet in 2017.

Created by Italian designer Antonio Vietri, the Moon Star Shoes were the starring attraction of the 2019 MIDE (Made in Italy, Designed in Emirates) Fashion Week in Dubai, United Arab Emirates. The platform sandals were reportedly valued at $19.9 million at the time. They featured solid gold heels sculpted to resemble the famed Burj Khalifa tower, as well as swirling embellishments with 30-carat diamonds and even a bit of meteorite found in Argentina in 1576.

One of the four surviving pairs of ruby slippers worn by Judy Garland in 1939’s “The Wizard of Oz” shattered the record for footwear (and entertainment memorabilia) when it was sold by Heritage Auctions on Dec. 7, 2024, for $28 million. (With the buyers’ premium, the total price jumped to $32.5 million.) These shoes were famously stolen from the Judy Garland Museum in Grand Rapids, Minn., in 2005 and then recovered 13 years later as part of an FBI raid — thus earning them the new nickname “The Stolen Pair.” All of Dorothy’s ruby slippers were designed by Gilbert Adrian, MGM’s chief costume designer, and made by Western Costume Company. After sitting for decades in MGM’s deep storage, these shoes made their way into the hands of costumer Kent Warner. He eventually sold them to collector Michael Shaw, who loaned them to the Judy Garland Museum. Interestingly they are a mismatched pair, believed to be the sisters of the ruby slippers at the Smithsonian Institution.