What Is the Next Big "Ugly" Shoe?

It was a clomp heard 'round the world.

When Taylor Swift strolled through New York City this September, the superstar wasn’t teetering in her signature sweetheart pumps. Instead, she chose the Robin boot, a lug-soled leather slab from The Row that resembles orthopedic workwear and costs roughly half the average American mortgage. The shoes are equal parts strange and amazing; they are also sold out.

Swift isn’t the only one swapping dainty footwear for something ... less pretty. At New York Fashion Week, hot tickets like Proenza Schouler and 3.1 Phillip Lim styled their models in wide mesh flats that resembled lobster nets. Flouncy princess skirts from the Hollywood It label Staud came with flattened shoe-socks. (Imagine old-school Keds run over by a car.) And at the Gen Z favorite Collina Strada, creative director Hillary Taymour collaborated with Ugg on chunky Mary Janes with threateningly cool spikes at the heel and toe.

Taymour called the shoes “fearless and dressed for a smile.” We'd offer a different designation: The latest in a long line of clompers labeled simply “The Ugly Shoe.”

The Rise (and Rise...) of the "Ugly" Shoe

Beauty is expansive, and nothing is “ugly” except blind hatred and the way my hair looks when I run out of Kerastase. But that’s okay because “The Ugly Shoe” isn’t unattractive, per se; it’s just weird, unfamiliar, and more challenging to the eye than a sleek stiletto. In the words of fashion stylist Masha Orlov, who began her career modeling for Zac Posen before going behind the scenes with brands like Dior and Nordstrom, “the size and beauty of your heel used to represent your female power. They would say, ‘My heels are bigger than your dick!’ But that all changed a few years ago… Now ugly is good. Sometimes, it can be great.”

Take the Maison Margiela Tabi, a shoe with a separate space for the big toe, which was arguably the first official “Ugly” footwear to take off and an IYKYK symbol of the style elite. After debuting in 1988, the shoe became a favorite of Paris’ emerging designers, including future fashion superstars like Raf Simons, the co-creative director at Prada. 

By the mid-1990s, the Tabi had been reimagined as a boot and a heel — and embraced by front-row royalty like Chloë Sevigny and Sarah Jessica Parker. In 2021, they became downright mainstream, as Kim Kardashian flashed the Tabi x Reebok collection on her Instagram. Now Olivia Rodrigo and Dua Lipa wear them in paparazzi snaps. Fashion writer Arabella Sicardi called the Tabi “the most divisive thing I own” on the retail site Ssense, where pairs can be purchased for more than $1,200. Over Labor Day Weekend, designer Alexis Dougé went viral on TikTok when she revealed a Tinder date had stolen her beloved Tabis while visiting her apartment. They were later returned to the owner at Grand Central Station.

Why does the Tabi still hold sway? “They’re the ultimate eff you to people who don’t get fashion,” says Amy Evans, 19, a New York design student who recently bought her first pair after saving up since her Bat Mitzvah. “Or people who are like, ‘Girls should wear pretty things.’”

That rebellious streak helps give some “Ugly” shoes their legs. Anti-heels have long signified a silent protest of girly glamour, especially in times of cultural upheaval. Take the ‘60s, when traditional round pumps were dumped for square-toed silver platforms, and the ‘90s, when Gen X raised their voices for human rights and clean energy as Donna Martin crossed the graduation stage in a pair of scuffed Doc Martens. In both cases, shoes were used to stomp all over the idea that women’s clothes should be “pretty” above all else. 

Since then, several “Ugly” shoes have piqued the style industry’s interest — the Alexander McQueen “Armadillo heel” of 2010, the Marc Jacobs 2012 pilgrim loafer, and Saint Laurent’s bedazzled rain boots from the 2015 runway come to mind. In 2019, a bubblegum pink pair of Balenciaga’s infamous platform Crocs joined the archive at the famous Costume Institute of the Metropolitan Museum of Art.

But “Ugly” shoes aren’t just a designer whim or a barometer for social change. In today’s street-style-pics-or-it-didn’t-happen fashion cycle, wild soles can also be essential to getting noticed. Fashion can create serious currency in the attention economy, and if the right “Ugly” shoe can get its owner closer to fame, some will see it as a worthy investment — even if it means spending real money for the mere possibility of online likes.  

The big bang of “Ugly, but make it fashion, but also make it viral!” happened this past February, when MSCHF debuted their Big Red Boots. The headline-loving label also once made Birkenstocks out of Birkin bags, but this particular style transcended the realm of in-joke and became a genuine status accessory. 

During the spring 2023 runway cycle, the Big Red Boots were on every major street style site and scored features in news outlets like The New York Times, The Washington Post, and People. Janelle Monae and model Sarah Snyder wore them; their TikTok hashtag currently has more than 324 million views. (The population of America is 331.9 million people, BTW.)

In July, the Big Red Boots got a sequel courtesy of a Crocs collaboration. Bright yellow and featuring the signature Croc heel strap, the boots are basically Spongebob Square Pants in footwear form. Victoria Beckham and Paris Hilton have already been photographed in them, and this meme? Chef’s kiss. 

The Future Is Flat

The “Ugly” shoe isn’t going anywhere, but it is evolving, and there’s a new crop just on the horizon. One top contender for fashion’s next viral “Ugly” shoe: Vintage-inspired bowling shoes, a TikTok favorite as seen on Gen Z star Elle Fanning, Millennial favorite Amber Tamblyn, and a surprising amount of Pinterest posts.

Influencer Clara Perlmutter (@tinyjewishgirl) is betting that her 1 million followers will love the “dream pair” of vintage Prada bowling shoes from 2001 that she just found on eBay. “I’ve been working on my ability to slay in a casual way,” she notes, explaining that the bowling shoes, along with “geriatric trainers that look like what my grandparents wear for comfort,” pair well with leather pants, long skirts, and jeans. There’s also the Onitsuka Tiger, which has the same geometric seams as a bowling shoe but with a more elevated, streamlined shape. Kaia Gerber and Kristen Stewart are wearing them on coffee runs, and editors like HighSnobiety’s Willa Bennet are styling them with satin ribbons subbed for normal shoelaces, adding a super cute edge to the "Ugly" shoe. 

The Martine Rose x Nike mules are also in the running as the next big (weird) fashion thing of 2023, which is good since you can actually run in them. Thanks to Rose’s must-have status among hypebeasts and fashion insiders, the sneakers made early celebrity appearances on the feet of Kendrick Lamar and Hailey Bieber. In a recent street style shoot, the Little Book of New York Style author Kristen Bateman paired them with a neon green Selkie dress and tweed Chanel purse. “I normally hate sneakers,” she said. “But the square toe and corkscrew sole are just so unique. They really sold me... I did think they’d feel kind of ‘bouncy’ because of the sole, and they don’t! But they’re easy and look hard.”

Fashion fans are also leaning into a recent collection of misshapen ballet flats, with a pointier silhouette and see-through materials that expose the toes. Bottega Veneta, The Row, and Sandy Liang were early adopters; now, even Zara sells a pair. “When the mesh ballet flats from Khaite came back in stock, our readers flipped,” says Jessica Graves, the creative director and editor who helms The Love List, a shopping newsletter for luxury fashion. Graves cites Alaïa’s version of the fishnet flat as another e-comm driver. Why the popularity? “It’s different; it’s weird… and it has a Venetian slipper vibe that really appeals to people who love Renaissance art or maybe studied art history in college. The shape is strange to the eye, but if you have that reference point, you can place it. So it feels very in-the-know.” 

If you’ve been following the InStyle Instagram account, you know our editors have been puddle-jumping from one runway show to the next, thanks to a series of relentless thunderstorms that turned New York City into a very chic swamp.

Between global warming and economic jitters, it’s no longer just Manhattanites who want to walk everywhere — and therefore need a pair of shoes that can endure the daily wear of taking public transit. Real talk? You can’t run for the last train home in a pair of 4-inch stilettos unless you’re ready to fall flat on your face. (Yep, I’ve done this. No, I don’t recommend it, even for the new Valentino pumps.)

Eco-activist and designer Erin Beatty of Rentrayage just sent her version of the "Ugly" shoe down the runway: a subversive take on a kitten heel with actual cat ears creeping up the front. Her mindset? “When I think of what I want to wear to the apocalypse, I want to be comfortable. But I also want to be, you know, cool. Like, ‘Hey, we’re here! We’re surviving! We make it look pretty good!’” See you there in my Martine Rose x Nike mules.