If the viral (and insanely divisive) transparent footwear featured in June’s Saint Laurent men’s show made anything, ahem, clear, it’s that statement-making shoes are staging a comeback. The appetite for shocking fashion tends to rise and fall with the season, but funky footwear has been tiptoeing onto the market for years and seems to be here to stay. McQueen, Loewe and Dior are just a few brands pushing the boundaries of late, to great success.
As surrealism and maximalism firm up their grip on consumers hungering for loud luxury, bizarre motifs are gaining a foothold in pumps, sandals and boots. For the Carrie Bradshaw–level shoe maven, vintage treasures in this vein abound. Here, we’ve compiled a selection of whimsical designer shoes that will speak to any eccentric collector’s sole.
Maison Martin Margiela Tabi Boots
The Margiela Tabi has perhaps the most fiercely debated silhouette in modern popular fashion. Introduced in 1988 by Martin Margiela, the boot was instantly a subversive success and a subject of traditionalist ridicule. Its bifucated toe, derived from 15th-century Japanese socks, has evolved into a token of cultural currency for fashion connoisseurs.
This pair of Tabi boots, from 1995, is hand-painted, as evidenced by the brush marks and ombré finish that climbs up to the ankle. Public opinion on Tabis will likely always be split, but that division just cements their icon status.
Schiaparelli Trompe l’Oeil Sandals
Elsa Schiaparelli famously turned shoes into headwear; Daniel Roseberry is turning them into art for (and of) the feet. Under Roseberry’s direction, shoes are some of Schiaparelli’s most coveted and outlandish accessories — just consider Zendaya’s couture bird heels and the hyperrealistic kitten slip-ons in the designer’s recent fall collection. Perhaps his most iconic footwear element is the gilded toe cap, like the ones on these trompe l’oeil sandals, molded to resemble toes. An additional attraction: This homage to the house’s long fascination with anatomy makes a fresh pedicure unnecessary.
Prada Geisha Platforms
From flames to fairies, Prada has long offered well-heeled fashionistas styles catering to their sense of adventure. These 2013 Prada embellished platforms whisk their wearer to the Far East, combining delicate florals with an homage to the traditional geta sandal. The double platform almost looks like a reverse reflection of a single sole, adding a dreamy architectural contrast to the feminine design. As a practical bonus, these are also likely the most comfortable shoes on this list.
Giuseppe Zanotti Fish-Bone Sandals
One man’s trash is Giuseppe Zanotti’s treasure. The T-straps on these crystal-encrusted Piranha sandals are a glamorous take on discarded fish bones. The rows of bedazzled teeth on the ankle — these are piranha skeletons, after all — give the shoes an extra bite. And since Samantha Jones wore a pair (while covered in sushi) in the first Sex and the City movie, the sandals boast her coveted seal of approval.
Versace x Haas Brothers Triple-Platform Bondage Boots
Often, unexpected alliances produce the most thrilling outcomes. Take these triple-platform Bondage ankle boots from Versace’s 2013 collaboration with the Haas Brothers. Versace is celebrated for endowing Italian fashion with glittering sex appeal, while the Haas Brothers are known for creating biomorphic, hallucinogenic fine art and design. These discordant influences converge with tantalizing drama in the Bondage boots. The strapped leather upper harks back to Gianni Versace’s famed Miss S&M collection, while the stacked, honeycomb-embossed platform alludes to organic motifs in the Haas Brothers’ signature gilded finish.
Miu Miu Pink Faux-Fur and Crystal Block-Heel Sandals
Miuccia Prada must have quite the sweet tooth. Miu Miu, Prada’s sister label, named after the designer, often displays a spritelier aesthetic than Prada itself, as witness these Miu Miu Fall/Winter 2017 sandals. The furry confections’ block heel, crystal clasp and exuberant faux-fur details scream delectable frivolity. Even on the feet, they can’t help calling to mind cotton candy.
Vivienne Westwood Rocking Horse Shoes
Vivienne Westwood’s 1980s Rocking Horse shoes stand somewhere between closet staples and museum treasures. Introduced in the designer’s 1987 Harris Tweed collection, the wooden-platform footwear is part of fashion history. Beyond adding a few inches to the wearers’ height, the curved soles make them roll forward as they walk, evoking the motion of a child’s rocking horse. The ballet-slipper-inspired upper, with its crisscrossing laces, provides an additional hit of nostalgia.
Alexander McQueen Oyster-Shell Wedge Sandals
Sculptural, gravity-defying footwear is in the Alexander McQueen brand’s DNA. McQueen himself presented the world with a triumph of sci-fi fashion engineering in the 2010 Armadillo boot, and his mentee and successor, Sarah Burton, continued in his footsteps with the 2012 Oyster-Shell wedge. The sandals display the same aquatic-futurist sensibility that characterized the Plato’s Atlantis collection, which introduced the Armadillo. Their cantilevered heels gleam with a dramatic gold-and-black gradient, their sinuous forms recalling the polished ribs of a shell. The tentacle-like straps wind symmetrically up to the ankle, enclosing the foot in another dark, ethereal masterpiece from the house.
Loewe Petal Brush Sandals
In 2026, no discussion of unusual footwear would be complete without mentioning Loewe. During his tenure at the storied Spanish house, Jonathan Anderson revolutionized its aesthetic, making it synonymous with boundary-pushing illusionism. Techniques like trompe l’oeil and micromosaics elevated ready-to-wear fashion to Pop art, as in these Petal Brush heels from 2023. They belong to a collection in which nail-polish bottles, broken eggs and, in their case, fluffy makeup brushes stand in for stilettos, causing a double take from onlookers with every step.
Christian Louboutin Spiked Kate Max Boots
Dangerous might be used as an ironic word of praise for a pair of heels, but these Spiked Kate Max boots should actually be worn with caution. The Christian Louboutin creations feature a strip of chrome claws on the back of each shaft, which will probably make the person behind you take a step back. Although they are unlikely to cause any real injury, their intimidating effect is supremely satisfying.
Balenciaga by Nicolas Ghesquière Gladiator Sandals
Balenciaga’s Gladiator sandals became instant favorites in Rihanna’s fashion archive when she stepped out in them in 2008. Their bold chevron print, knee-high shin guards and rows of buckles are enhanced by colorful geometric enamel tiles on the heel that push the design even further into maximalist territory.
Off-White by Virgil Abloh Meteor Shower Boots
A natural disruptor, the late Virgil Abloh liked to poke holes in things. He challenged the status quo at Louis Vuitton Men’s and revolutionized streetwear with his own brand, Off-White. There, he poked literal holes in his Meteor Shower boots in 2020. The wedge heel and wide shaft create a futuristic look that evokes both moon landing and Swiss cheese. Whatever you see in them, ample foot ventilation is guaranteed. If only those clear Saint Laurents could say the same.
