They’re chunky. Clunky. Questionably shaped. And somehow… they’re iconic. Fashion has a funny way of turning the weird, the ugly, and the downright ridiculous into must-haves—and no category proves that more than shoes. From dad sneakers to platform hooves, these pairs made us do a double take—and then rush to add them to cart.
Love them or hate them, they’ve stomped their way from “what are those?!” to certified cult classics. Here are the 10 ugliest shoes that defied the odds, dominated trends, and became fashion legends. Brace yourself: beauty is definitely in the eye of the beholder.
1. Balenciaga Triple S Sneakers
Chunky fashion became a reality with these $900 sneakers that redefined streetwear. These sneakers scream dad-core, yet they became an unavoidable trend. Initially mocked for their oversized, bulky form, these shoes started a fashion wave.
The Triple S’s triple-layered soles might appear complex, but they symbolize a new fashion movement. A fusion of athletic design and high fashion, they are more than a shoe; they represent a cultural shift. Wearing them is a statement of embracing bold, unapologetic style. They remain a staple among fashion enthusiasts who love challenging norms.
2. Crocs Classic Clogs
Once the laughingstock of the shoe world, Crocs clogs have become an unexpected fashion hero. Known for their quirky design and vibrant colors, they were initially mocked for their appearance. Today, they’re a symbol of comfort and style.
Collaborations with high-fashion brands like Balenciaga have elevated them to new heights. These clogs are now seen on celebrities and fashionistas alike. Their journey from ridicule to high fashion is a testament to their unexpected influence. Comfort has never looked so chic, proving that fashion can be both fun and practical.
3. Maison Margiela Tabi Boots
Maison Margiela’s Tabi Boots aren’t your average footwear. Inspired by Japanese tabi socks, these split-toe boots look like they belong to a fashion-forward centaur. Their design is avant-garde and has been a staple in the fashion world since their runway debut in 1988.
Worn by the daring, these boots are now a symbol of bold, experimental fashion. They challenge the ordinary, inviting wearers to embrace their unique style. Despite initial skepticism, they’ve become a beloved part of high fashion, often seen in artistic circles and stylish gatherings.
4. Birkenstock Boston Clogs
These clogs have made the leap from practical to iconic. Known for their comfort and simple design, they’ve been a staple in casual footwear. Originally associated with dads and art teachers, they’ve found a new audience. Fashion influencers have embraced them for their laid-back vibe and versatility.
The Boston Clogs’ rise is a blend of functionality and fashion appeal. They’ve become a favorite for those who appreciate understated style. Loved for their comfort, they are the go-to for relaxed fashion. They prove that sometimes, simplicity is the ultimate sophistication.
5. UGG Classic Boots
UGG boots have defied their shapeless reputation to become a winter essential. Once seen as basic, these boots are now a wardrobe staple. Known for their warmth and comfort, they faced initial mockery but have since won over the fashion world.
Collaborations with designers have given them a fresh appeal. They are celebrated during colder months for their practicality and cozy feel. The boots’ resurgence showcases their adaptability. They remain popular among all ages, proving that comfort can seamlessly blend with style, making them a beloved choice in winter fashion.
6. Kanye West’s Yeezy Foam Runners
Kanye West’s Yeezy Foam Runners are neither typical shoes nor mere art objects. They resemble something extraterrestrial, challenging conventional designs. Their debut was divisive, but they quickly sold out. These runners are sculptural, with a silhouette that intrigues and confounds.
They’re a testament to Kanye’s boundary-pushing creativity and have become a sought-after piece in sneaker culture. Loved for their unorthodox style, they represent innovation at its finest. They cater to those who dare to be different, solidifying their status as a contemporary fashion icon among sneaker enthusiasts.
7. Vivienne Westwood Super Elevated Ghillie Platforms
Vivienne Westwood’s platforms are as daring as they are iconic. These shoes are a piece of fashion history, known for their towering height and unique design. Models have famously stumbled while wearing them, a testament to their challenging nature.
Despite this, they remain a symbol of rebellion and style. Their legacy continues as they inspire new generations of designers. These platforms are not just shoes; they’re an attitude, embodying Westwood’s fearless fashion vision. Owning a pair is like owning a piece of art, a statement of individuality and boldness in the fashion world.
8. Nike Benassi Slides (Worn with Socks)
Nike Benassi Slides, once reserved for locker rooms, have found their place in everyday fashion. Worn with socks, they’ve become a style statement. Initially seen as unfashionable, they’ve gained popularity among the young. Embracing comfort, these slides are now a favorite for casual, athleisure looks. Their transformation highlights the shift towards comfort-driven fashion.
They represent a laid-back lifestyle, perfect for those who value ease. The combination with socks adds a playful twist, making them a standout in contemporary footwear. It’s a testament to how casual can turn chic.
9. Gucci Screener Sneakers
Gucci’s Screener Sneakers are a paradox of luxury and distress. Intentionally pre-dirtied, they play with perceptions of newness and value. These sneakers challenge traditional notions of pristine luxury. Priced at over $800, they are a bold statement on the current fashion landscape.
Despite confusion, they’ve become a status symbol. Their worn look is deliberate, celebrating imperfection. They’re adored by those who appreciate fashion’s rebellious side. These sneakers are more than footwear; they are a commentary on luxury and authenticity, embraced by fashion-forward individuals who thrive on breaking norms.
10. Platform Crocs (Balenciaga x Crocs)
The collaboration between Balenciaga and Crocs resulted in something truly unexpected: platform Crocs. These $850 shoes defy logic, combining height with casual comfort. Complete with Jibbitz charms, they are a playful twist on traditional Crocs.
Their debut on runways surprised many, yet they sold out quickly. They reflect the whimsical side of fashion, where the absurd becomes desirable. These platforms are a daring take on luxury footwear, loved by those who enjoy the unconventional. It’s a fusion of practicality and high fashion, proving that even the unexpected can become iconic.