The 50 Ugliest Shoes in History
There are all sorts of reasons that shoes turn ugly. And all sorts of reasons we turn to ugly shoes. Feet, themselves, are an anatomical oddity, and ugly shoes either sacrifice aesthetics for podiatric practicality, or ignore function for the sake of fetish and fashion fantasy. With either, it can quickly go too far: Sometimes a shoe is too avant-garde for its own good, with some of the best footwear designers (ahem, Miuccia Prada) putting pairs down the runway that you won’t be blowing your paycheck on. In other cases, comfort comes at the expense of fashion, and the results — UGGs, Birkentstocks, Doc Martens — end up homely. Still, fashion is fickle; one day, any of these styles on our list may be cool again, or at least ironically embraced. For now, they prove that there are far more ugly pairs in the world than pretty ones. And because we all own some ourselves, tell us what’s missing in the comments section.
Crocs, 2002 Molded from a proprietary material called croslite, Crocs are lightweight, waterproof and bacteria resistant. But unless you’re in su...
Crocs, 2002 Molded from a proprietary material called croslite, Crocs are lightweight, waterproof and bacteria resistant. But unless you’re in surgery, a restaurant kitchen, or kindergarten, they’re one other thing, too: unnecessary.
Photo: Cate Gillon/Getty Images
Jean Paul Gaultier 1977
Les Plongeuses Fin-Heels, S/S 2007 For his thirtieth anniversary, full of his greatest hits, Gaultier recreated his...
Jean Paul Gaultier 1977
Les Plongeuses Fin-Heels, S/S 2007 For his thirtieth anniversary, full of his greatest hits, Gaultier recreated his 1977 hooded, one-piece bathing suit. He paired it, naturally, with high-heeled lace-up fins – perfect for all those impending underwater cocktail parties.
Viktor and Rolf Cutaway Knee-High Boots, S/S 2010 During the recession, this design duo reacted by literally cutting back. With a cutaway va...
Viktor and Rolf Cutaway Knee-High Boots, S/S 2010 During the recession, this design duo reacted by literally cutting back. With a cutaway vamp, flesh-toned boots were transformed into platform pumps with matching shin-guards, plus some “let them eat cake” decoration to keep the irony going strong.
Photo: Imaxtree.com
Mihai Albu Structures and Megastructures Shoes, F/W 2010 With his triple-decker platform, the self-proclaimed "Shoe Architect" engineer...
Mihai Albu Structures and Megastructures Shoes, F/W 2010 With his triple-decker platform, the self-proclaimed "Shoe Architect" engineered his stacked shoe to be a foot tall. Equally impressive? The woman capable of walking in his gravity-defying mega-shoe.
Photo: Vadim Ghirda/AP
Kobi Levi Double Boots, 2000 Worn by Lady Gaga in her Born This Way video, Israeli designer Kobi Levi’s double boots look equally awkward coming ...
Kobi Levi Double Boots, 2000 Worn by Lady Gaga in her Born This Way video, Israeli designer Kobi Levi’s double boots look equally awkward coming and going.
Photo: Virtual Shoe Museum
Prada Acrylic and Crystal Sandals, S/S 2010 A champion of "ugly beauty," Miuccia delivered with her crystal-strewn sandal-iers for S/S ...
Prada Acrylic and Crystal Sandals, S/S 2010 A champion of "ugly beauty," Miuccia delivered with her crystal-strewn sandal-iers for S/S 2010. With their mix of acrylic and cut crystal, she described them (and the rest of the collection) as a reflection of "how life is today. High and low, palazzos, and the popular." We just wish they lit up.
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BONUS! Zoom in to get a closer look at the toe-nail that was added for this look.
Photo: Imaxtree.com
Nicholas Kirkwood for Meadham Kirchhoff Lamé Platform Sandals, S/S 2012 Ruched and ruffled lamé, furry pom-poms, glitter –all ...
Nicholas Kirkwood for Meadham Kirchhoff Lamé Platform Sandals, S/S 2012 Ruched and ruffled lamé, furry pom-poms, glitter –all in one sandal. They’re the shoe equivalent of a piñata or a My Little Pony birthday cake. This collection critiqued codes of girlishness, but these felt more genuinely Sweet Sixteen. Photo: Antonello Trio/Imaxtree.com/ANTONELLO TRIO/IMAXTREE.COM
Doc Martens Boots, 1945 After a 1945 skiing accident, Dr. Klaus Maertens needed a shoe with an air-filled sole. He sold the design, British skinh...
Doc Martens Boots, 1945 After a 1945 skiing accident, Dr. Klaus Maertens needed a shoe with an air-filled sole. He sold the design, British skinheads embraced it, and the shoe became associated with violence and bigotry. Since then, Docs have been tamed – but the aesthetics are still all wrong. Photo: redsnapper/Alamy
Iris Schieferstein Vegas Girl I Heels, 2009 Crafted from actual horse hooves, the shoes have attracted the attention of animal rights groups...
Iris Schieferstein Vegas Girl I Heels, 2009 Crafted from actual horse hooves, the shoes have attracted the attention of animal rights groups and Lady Gaga. The latter ordered a custom, heel-free version with pink laces. Photo: Iris Schieferstein/Solent News/AP
Bubbleflops, circa 2010 Originally a fashion fad in Korea beloved by K-popstars, each pair of wedged flip-flops has charms that follow a theme. F...
Bubbleflops, circa 2010 Originally a fashion fad in Korea beloved by K-popstars, each pair of wedged flip-flops has charms that follow a theme. For bathtime, little rubber duckie adornments. For weddings, tiny diamond rings. For anytime, just plain tacky. Photo: Courtesy of Badfairy.net
Rick Owens Covered Wedge Boots, S/S 2009 These tented black boots look like trash bags lashed with gaffer tape. By disguising a wedge boot under ...
Rick Owens Covered Wedge Boots, S/S 2009 These tented black boots look like trash bags lashed with gaffer tape. By disguising a wedge boot under a fit-and-flare leather pant, they also remind us of a gothic take on Mamma Mia, all ABBA but totally sinister. Photo: Imaxtree.com
Vibram FiveFingers, 2005 Obsessive athletes continue to go on about "barefoot running," turning their feet into something that looks am...
Vibram FiveFingers, 2005 Obsessive athletes continue to go on about "barefoot running," turning their feet into something that looks amphibious or simian with these affordably ugly sneakers. Sadder still, they are here to stay. Photo: Whitehotpix/Newscom
Anna Korshun Gray Ankleboots, 2010 This Belarusian designer’s gray ankleboots draw “from communist upbringing,” and the idea was that the au...
Anna Korshun Gray Ankleboots, 2010 This Belarusian designer’s gray ankleboots draw “from communist upbringing,” and the idea was that the austerity would eliminate fashions’ seasonal whims. It actually just looks like the model’s wearing a shoebox. Photo: Courtesy of Anna Korshun
Chopines, circa 16th Century in Italy Venitian chopines were platform overshoes that were the pinnacle of 16th century fashion. Constructed...
Chopines, circa 16th Century in Italy Venitian chopines were platform overshoes that were the pinnacle of 16th century fashion. Constructed with bases of cork or metal, and reaching heights up to 20 inches, chopines were worn by Venetian noblewomen as status symbols. Higher shoes indicated higher rank, which is unfortunate for the rich. Photo: Fondazione Musei Civici di Venezia/AP
Birkenstocks, 1966 In 1966, Margot Fraser returned from a German spa vacation with a pair of contoured footbed sandals, then began importing Birk...
Birkenstocks, 1966 In 1966, Margot Fraser returned from a German spa vacation with a pair of contoured footbed sandals, then began importing Birkenstocks to the U.S. With their unisex shape and promise of cork comfort, Birkenstocks have attracted an odd mix of hippies, college kids, and celebrities ever since. No need to join the comune.
Photo: Daniel Dillon/Alamy
Céline Mink Lined Sandals, S/S 2012 Maybe Phoebe Philo had scraps of mink leftover from last season’s mixed media sweatshirts? Her latest ...
Céline Mink Lined Sandals, S/S 2012 Maybe Phoebe Philo had scraps of mink leftover from last season’s mixed media sweatshirts? Her latest sandals remixed Birkenstock inspired-styles with plush linings of dyed mink. With their perverse eroticism, these furkenstocks are equal parts Helmut Newton and Jim Henson.
Photo: Imaxtree
UGGs, 1978 We get it, they're comfortable. Uggs were born in Australia in 1920 – but it took nearly 100 hundred years for them to ruin outfits th...
UGGs, 1978 We get it, they're comfortable. Uggs were born in Australia in 1920 – but it took nearly 100 hundred years for them to ruin outfits the world over. Credit goes to a man named Brian Smith, who branded Ugg in 1978. And to US Weekly.
Photo: Frank Micelotta/Getty Images
MM6 Maison Martin Margiela Stretch 'Zori' Boots, 2010 If wearing socks with sandals is a fashion misdemeanor, wearing sandal-socks is definitely ...
MM6 Maison Martin Margiela Stretch 'Zori' Boots, 2010 If wearing socks with sandals is a fashion misdemeanor, wearing sandal-socks is definitely a fashion felony. A cross between a flip-flop, a boot, and a pair of knee-high stockings, these Margielas have a certain geriatric charm. They’d go great with your walker.
Topless Shoes, invented at Zhejiang University in 2011 Instead of opening only at the ankle, these have a slit that runs the length of the f...
Topless Shoes, invented at Zhejiang University in 2011 Instead of opening only at the ankle, these have a slit that runs the length of the foot, intended for those who can't put on conventional shoes. Good idea, but it’s still better to go barefoot than topless.
Giuseppe Zanotti Design E00063 Multi-Leather Boots, 2010 Red, white, and ew. Giuseppe Zanotti's white, open-toed ankle boots took patriotism...
Giuseppe Zanotti Design E00063 Multi-Leather Boots, 2010 Red, white, and ew. Giuseppe Zanotti's white, open-toed ankle boots took patriotism to another level, with that bald-eagle-and-tattered-American-flag effect. Full of crystals, these retailed for $840. And they sold out.
Photo: Dimitrios Kambouris/2009 WireImage
Balenciaga “Bobine” Sandals and Pumps, F/W 2012 Inspired by corporate America, the open-toed sandals and pumps—some leather, some color-blocked, ...
Balenciaga “Bobine” Sandals and Pumps, F/W 2012 Inspired by corporate America, the open-toed sandals and pumps—some leather, some color-blocked, some crocodile—featured sneaker-style grommets and shoelaces like the Reeboks that Melanie Griffith wore in Working Girl. With their extra-long laces, the runway versions not only trussed the foot like poultry but also bound the ankle.
Photo: Imaxtree
Kangoo Jumps, 1994 The health benefits of so-called "rebounding shoes" have been studied by NASA and include lower impact to the joints...
Kangoo Jumps, 1994 The health benefits of so-called "rebounding shoes" have been studied by NASA and include lower impact to the joints, increased cardiovascular endurance, and weight loss. You can decide if looking like Robocop on stilts is worth it.
Photo: Ruaridh Stewart/ZUMA Press/Corbis
Lotus-Shoes, Chinese Song Dynasty (960-1279 A.D.) An ancient Chinese practice, footbinding originated in the Song dynasty and continued well into...
Lotus-Shoes, Chinese Song Dynasty (960-1279 A.D.) An ancient Chinese practice, footbinding originated in the Song dynasty and continued well into the 20th century. Young girls’ toes were broken and bound beneath the sole, restricting growth and deforming the foot. The ideal size was 3 inches – the “golden-lotus” – which was considered highly erotic and could earn a good marriage.
Photo: Science & Society Picture Library/Getty Images
Designer Moon Boots, the Aughts Inspired by the moon landing, Giancarlo Zanatta created Moon Boots in 1971. Over the last 40 years, 20 million pa...
Designer Moon Boots, the Aughts Inspired by the moon landing, Giancarlo Zanatta created Moon Boots in 1971. Over the last 40 years, 20 million pairs of the Technica originals have sold. Pucci, Marc Jacobs, Chanel and Dior all copied them, but no matter how you dress them up (with logos or chains or fur) they still look like foot-shaped sleeping bags. Photo: Imaxtree.com
Designer "Tevas," S/S 2011 First conceived by a white-water rafter in 1983, Teva-style sandles were all over the men’s runways in Sprin...
Designer "Tevas," S/S 2011 First conceived by a white-water rafter in 1983, Teva-style sandles were all over the men’s runways in Spring 2011, when Bottega Veneta, Richard Chai, and Lanvin all showed them. We haven’t tested, but maybe they look better wet? Photo: Imaxtree.com
Marc Jacobs Pumps, S/S 2008 In conjunction with a fashion show that ran backward from finale to first look, Marc Jacobs designed a reverse heel. ...
Marc Jacobs Pumps, S/S 2008 In conjunction with a fashion show that ran backward from finale to first look, Marc Jacobs designed a reverse heel. Since it’s cantilevered, the trompe l’oeil pump gives the impression of a stumble-in-progress. Sexy, we know. Photo: Imaxtree.com
TOMS Shoes, 2006 Philanthropy is admirable, but from a strictly aesthetic standpoint, TOMS classics look like a bandage stitched to an eraser.&nb...
TOMS Shoes, 2006 Philanthropy is admirable, but from a strictly aesthetic standpoint, TOMS classics look like a bandage stitched to an eraser. Photo: Tomsshoe.com
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Marc Jacobs Rhinestone Buckle Shoes, F/W 2012 Taking cues from Dr. Seuss and Plymouth Rock, Jacobs showed giant fur fedoras, with rhinestone buck...
Marc Jacobs Rhinestone Buckle Shoes, F/W 2012 Taking cues from Dr. Seuss and Plymouth Rock, Jacobs showed giant fur fedoras, with rhinestone buckled flats and heels. Perhaps tellingly, they walked to three versions of the Oliver! tune: “Who Will Buy?”
Photo: Chris Moore/Catwalking/Getty Images
Gianmarco Lorenzi Knee-High Denim Boots, 2012 Want to look like an extra from Whitesnake video? Gianmarco Lorenzi's knee-high, patchwork den...
Gianmarco Lorenzi Knee-High Denim Boots, 2012 Want to look like an extra from Whitesnake video? Gianmarco Lorenzi's knee-high, patchwork denim and lace, peep-toe, cut-away vamp, espadrille, wedge-boots have got you covered. By about a mile.
Louis Vuitton Daisy Half-Boots in Monogram Denim, S/S 2010 With its unique materials (ombré monogram denim, sheepskin, Mongolian lamb...
Louis Vuitton Daisy Half-Boots in Monogram Denim, S/S 2010 With its unique materials (ombré monogram denim, sheepskin, Mongolian lamb, wood, metal, and leather), and hybrid form (kitten-heeled, demi-boot, clog) you could call the "Daisy" a postmodern pastiche. But that might be a bit generous. Photo: Imaxtree.com
Marni Ballerina Flats, Pre-Fall 2012 With their Docs-styled lug soles and thick ankle-strap, Marni’s ballerinas are more clumsy than graceful.&nb...
Marni Ballerina Flats, Pre-Fall 2012 With their Docs-styled lug soles and thick ankle-strap, Marni’s ballerinas are more clumsy than graceful. The weighty flats were meant to anchor Consuelo Castiglioni’s 1950s teddy boy-inspired separates. But for teens of the 90s, they evoke all the anxiety of the My So-Called Life era.
Photo: Marni.com
Balenciaga Multicolored Plastic Techno-Sandal, F/W 2007 Five years ago, Nicolas Ghesquière outfitted his tribe of multicultural schoolgirl...
Balenciaga Multicolored Plastic Techno-Sandal, F/W 2007 Five years ago, Nicolas Ghesquière outfitted his tribe of multicultural schoolgirls in uniform blazers, jodhpurs, and "Lego" shoes. With multicolored plastic, the leather techno-sandal looked like a bad snowboard binding and were probably just as painful. At $4175, they hurt the pocketbook, too. Photo: Imaxtree.com
Aussie Soles SnUggs, 2012 Like a genetic experiment gone awry, the SnUgg is the hybrid offspring of a Croc and an Ugg. Combining...
Aussie Soles SnUggs, 2012 Like a genetic experiment gone awry, the SnUgg is the hybrid offspring of a Croc and an Ugg. Combining the warmth of a sheepskin lining with the waterproof comfort of a polymer sole, the SnUgg improves the appearance of neither shoe.
Christian Louboutin Bianca Platform Pump, 2012 Once upon a time, the platform pump was the footwear of choice for drag queens, working girls...
Christian Louboutin Bianca Platform Pump, 2012 Once upon a time, the platform pump was the footwear of choice for drag queens, working girls, and dominatrixes. But the hooker heel has turned its last trick. They’ve become banal and basic, spotted all over the Meatpacking District on any Saturday night.
Prada Pumps, F/W 2008 Miuccia is a master of innovation, but even that didn't excuse these heels, featuring folds and flaps of extra leather that...
Prada Pumps, F/W 2008 Miuccia is a master of innovation, but even that didn't excuse these heels, featuring folds and flaps of extra leather that were fastened with rubber-band straps. Thankfully, fish-feet never caught on.
Photo: Imaxtree.com
Earth Shoes, 1970 Developed by Danish yoga instructor Anne Kalsø in the late 1950s, Earth Shoes were introduced to the American public on ...
Earth Shoes, 1970 Developed by Danish yoga instructor Anne Kalsø in the late 1950s, Earth Shoes were introduced to the American public on the inaugural Earth Day in 1970. Inspired by "indigenous Brazilians," they feature a "negative heel" that realigns the body. Another case of physiology over fashion. Photo: Courtesy of Earth Inc.
Karl Müller Masai Barefoot Technology Shoes, 1996 Like all "toning shoes," MBTs feature a thick sole with a rounded heel desi...
Karl Müller Masai Barefoot Technology Shoes, 1996 Like all "toning shoes," MBTs feature a thick sole with a rounded heel designed to slightly destabilize the wearer and modify biomechanics. While the health benefits of that have been disputed by scientists and podiatrists, its ugliness remains incontrovertible.
Photo: Bill Hogan/Chicago Tribune/MCT/Newscom
Clear PVC shoes, S/S 2012 Vinyl shoes have appeared on and off since the swinging 60s, but a hoard of them overtook the S/S 2012 runways. W...
Clear PVC shoes, S/S 2012 Vinyl shoes have appeared on and off since the swinging 60s, but a hoard of them overtook the S/S 2012 runways. While they might look decent on the catwalk, we can't help but think of them cutting into our feet or fogging up with perspiration. Photo: Armando Grillo/Imaxtree.com/ARMANDO GRILLO/IMAXTREE.COM
Manolo Blahnik Okla Ankle Boots, 1994-2012 "Manolo Blahnik Timbs" – as Jay-Z called these – were launched in 1994 but reissued in ...
Manolo Blahnik Okla Ankle Boots, 1994-2012 "Manolo Blahnik Timbs" – as Jay-Z called these – were launched in 1994 but reissued in 2002, 2010, and 2012. As Beyonce and J.Lo have become fans of the stiletto version, prices have kept pace with inflation. Photo: Carla Thomas/The Fly Girl Guide
Brian Atwood Charleston Peep Toe Platform Ankle Boots, 2012 Dripping with a bordello's worth of upholstery tassels, the "Charlest...
Brian Atwood Charleston Peep Toe Platform Ankle Boots, 2012 Dripping with a bordello's worth of upholstery tassels, the "Charleston" has a Clydesdale look without the unsavory reality of actually killing and wearing a horses' hoof.
Acne Dandelion Open-Back High Heel Booties, S/S 2012 Acne’s latest looks like a shoe that’s been custom-hacked; as if you sawed off the back of a...
Acne Dandelion Open-Back High Heel Booties, S/S 2012 Acne’s latest looks like a shoe that’s been custom-hacked; as if you sawed off the back of a closed-toe flat and then glued on a pin-heel. They're a little butch, a little femme, a whole a lot unresolved. We could call them 'edgy' or editorial,' but those would just be euphemisms for ugly.
Photo: Matteo Volta/Imaxtree.com
Alexander McQueen Platform Heels, S/S 2010 The designer's Plato’s Atlantis collection was a brooding meditation on ecology, the Apocalypse, ...
Alexander McQueen Platform Heels, S/S 2010 The designer's Plato’s Atlantis collection was a brooding meditation on ecology, the Apocalypse, and evolution. And while "Armadillo" shoes got plenty of red-carpet wear, the Alien-inspired pumps here are clearly more menacing. Photo: Imaxtree.com
Céline Kiraro Sandals, S/S 2009 For her final effort at Céline, Croatian designer Ivana Omazic created a graffiti-printed, pla...
Céline Kiraro Sandals, S/S 2009 For her final effort at Céline, Croatian designer Ivana Omazic created a graffiti-printed, platform-wedge sandal with a missing-insole. With the thankless task of completing a collection after her dismissal was publicly announced, we can’t blame her for showing this. Photo: Imaxtree.com
Maco Custodio TriHEELatops, S/S 2011 Inspired by a childhood obsession with The Land Before Time, Filipino shoe designer Maco Custodio creat...
Maco Custodio TriHEELatops, S/S 2011 Inspired by a childhood obsession with The Land Before Time, Filipino shoe designer Maco Custodio created a platform pump with a snout-shaped bumper and a curly tail. And, of course, the triple Tricerotops heel. Photo: Courtesy of Maco Custudio
Nina Ricci Platform Lace-up Bootie, F/W 2009 In recent years, we’ve seen all manner of extreme platforms and treacherous heelless shoes. And you ...
Nina Ricci Platform Lace-up Bootie, F/W 2009 In recent years, we’ve seen all manner of extreme platforms and treacherous heelless shoes. And you can blame Olivier Theyskens’ last collection at Nina Ricci for kicking off this awful obsession. Photo: Imaxtree.com
Givenchy Bondage Oxfords, S/S 2009 For Tisci’s first menswear collection at Givenchy, shorts over leggings and lace shorts were a critical ...
Givenchy Bondage Oxfords, S/S 2009 For Tisci’s first menswear collection at Givenchy, shorts over leggings and lace shorts were a critical hit. Matching wing-tip bondage oxfords that buckled up the calf? Less so.
Photo: PIERRE VERDY/AFP/Getty Images
Alexander Wang “Simona” Sandals, F/W 2011 For a collection "poking fun at decadence and luxury," Alexander Wang’s sandals crossed fox-f...
Alexander Wang “Simona” Sandals, F/W 2011 For a collection "poking fun at decadence and luxury," Alexander Wang’s sandals crossed fox-fur, patent leather, and a detachable cape for a look that mixed mud-flap with Malibu Barbie. They're perfect for that brief meteorological window when it’s cold enough for fur but warm enough for open toes.
Photo: Stefan Gosatti/Getty Images
Prada Leather Tabi and Platform Overshoes, S/S 2013 Say konnichiwa to the future. Miuccia’s Spring runway mixed tabi – Japanese split-toe-so...
Prada Leather Tabi and Platform Overshoes, S/S 2013 Say konnichiwa to the future. Miuccia’s Spring runway mixed tabi – Japanese split-toe-socks – with platform overshoes. Because one pair of Pradas is never enough, the designer devised a way to double up. Be prepared for twice the sticker shock. Photo: Imaxtree
Converse Chuck Taylor 'XX Hi’ Knee High Sneaker,' 2012 Combining the tomboy ease of a sneaker with the sluttiness of a lace-up knee-high boot, th...
Converse Chuck Taylor 'XX Hi’ Knee High Sneaker,' 2012 Combining the tomboy ease of a sneaker with the sluttiness of a lace-up knee-high boot, the ‘XX Hi” has an awkward superhero/kinderwhore look. Maybe that’s why it’s one X shy of XXX?
Ahmet Baytar Bootbags, F/W 2010 This designer explains that his boot-bag hybrid accessory was inspired by the movie Mulholland Drive. We still do...
Ahmet Baytar Bootbags, F/W 2010 This designer explains that his boot-bag hybrid accessory was inspired by the movie Mulholland Drive. We still don’t get it.
Photo: Courtesy of Ahmet Baytar
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