Listicle: 10 ugly shoes that are actually really cute

Mules. Born as 15th-century French house slippers, they were never meant to step outside. Like the millennial employee, these backless styles overdeliver, people-please and shapeshift into whatever you need: Open-toe, pointy, wedge, platform, leather, fur-lined, even buckled and bejeweled. They peaked in the 1950s but every generation, there’s an attempt at a revival.

Birkenstock. Bland, brown, boring. But Birks don’t even try to be pretty. Users (and hippies, and grandpas and tourists) love them for the contoured orthopedic footbed. But celebrities such as Tyra Banks and Gwyneth Paltrow have slipped into Birks. The brand has released luxe-ish suede versions with Dior, and polka-dot special editions with Manolo Blahnik. The brand holds on to the OG style. And now, Gigi Hadid and Jennifer Lawrence are wearing it too.

Kitten heels. Too short. Too thin. Too weird. This polarising heel makes a comeback every few years and we hate it all over again. They’re not comfy, they make legs look stubby. Their reputation isn’t helped by being tied to Margaret Thatcher and Theresa May, though Carrie in Sex and the City gave them a brief ’90s outing. Those in the know say they’re about to be upstaged by the even shorter nipple heel. Katie Holmes and Alexa Chung are doing their best to make them happen.

Snoafer. 2025 is the year of the Frankenshoe. And leading the way is the snoafer (sneaker + loafer). Think ’90s dad sneakers fused with penny loafers: a little odd, but weirdly cute. Like if a dachshund were crossbred with a labrador. Bonus: no laces, no bitey leather, plus a cushy sole. New Balance, Puma, Nike have all come up with their versions. Upgrade with a Skechers x Martha Stewart leopard-print snoafer with a bedazzled bow.

Uggs. Every 2000s girlie’s holy trinity: Low-rise jeans, a hot-pink Moto Razr, and Uggs. Cameron Diaz, Paris Hilton and Britney Spears wore them as their “off-duty” look. The style was born in Australia, their name literally comes from the word “ugly”. They were branded as shapeless and made it to the 2010 list of “10 things men hate on women”. They also got banned from gyms, airport lounges, and Christopher Nolan sets (for being too distracting). Yet here they are again: Bella Hadid’s been wearing the micros, Selena Gomez the slip-ons.

Clogs. The original Crocs. In the 13th century, Dutch farmers wore these chunky wooden shoes (klomp, in Dutch) to stomp through mud. Somehow, they ended up on modern-day runways and dry city streets. Christian Louboutin hated them, but Dior and Hermès pushed out metal-studded, open-toed, memory-foam upgrades. Think of them as the SUV of shoes — sturdy, oversized, and weirdly versatile.

Vibram FiveFingers. Toe shoes. Stop trying to make them happen! Since 2004, they’ve promised the “barefoot experience” and better grip. Runners and climbers love them. The rest of us are freaked out because they remind us of the Creature from the Black Lagoon. But Blackpink’s Jennie wore them recently. And if she could make Labubus a thing, you know these will be too.

Orthopedic heels. The perfect shoe for your identity crisis. When your heart screams fashion but your feet beg for arch support, in come Balenciaga x Scholl with the “most comfortable heels ever made”. Not the most fashionable. They look like stilettos on sabbatical, or pumps that just checked into physiotherapy. But hey, you can’t win them all.

The Zero. Balenciaga’s latest creation feels less like fashion, more like a prank. It’s basically a wafer-thin sole with a toe notch. The brand calls it “barefoot freedom”; everyone else calls it the emperor’s new shoes. And at $450 a pop, you’re essentially paying to go barefoot in public. Will the designer brand pay for sole damage, cuts and foot damage? No they won’t.

From HT Brunch, September 6, 2025

Follow us on www.instagram.com/htbrunch