The Wrong-Shoe Theory Has Gone Feral in NYC, and It’s Actually Working
New York’s fashion crowd has officially taken the wrong-shoe theory to the next level this season. What started as a quirky styling hack has gone completely feral in the best way. Forget logic; it’s all about flipping the script. Think silk skirts paired with flip-flops, moto boots stomping alongside boxer shorts, and ultra-polished loafers grounding whispery sheer dresses. The formula? There isn’t one, and that’s exactly why it works.
What makes these looks hit isn’t just shock value—it’s the contrast. A floaty dress suddenly feels less precious with clunky loafers anchoring it. A pair of boxers (yes, actual boxer shorts) becomes elevated with the addition of sleek knee-high boots. Those barely-there flip-flops? When worn with something as traditionally elevated as a bias-cut skirt, they feel intentional, not lazy. The magic is in the clash.
New Yorkers, never ones to shy away from a fashion risk, are proving that unexpected footwear can be the key to making old pieces feel new again. And the best part is it’s easy. You don’t need a whole new wardrobe—just a fresh perspective. Those dainty ballet flats? Try them with cargo pants. Your chunkiest boots? Wear them with something silky and lacy. It’s all about the mix, the tension, and the attitude. The wrong-shoe theory isn’t just right. It’s redefining what cool looks like on the streets of NYC right now.
See some of our favorite summer outfits that employ the wrong-shoe theory below and shop the looks along the way.
A summery minidress styled with polished closed-toe heeled mules is an unexpected match, but it works so well.
LPA Giulia Mini Dress
Gia Borghini Abella Pumps
It’s the denim cutoff shorts with fancy pointed-toe heels here.
Good American Cutoff Carpenter Denim Shorts
Reformation Noreen Slingback Pump
A dainty dress with chunky clogs? We’re into it.
Free People Somebody to Love Mini Dress
Naturalizer Bailey Platform Mules
This is how you style a midi skirt with mid-calf leather boots.
ZARA Stretch Midi Skirt
Zadig&Voltaire Cara Boots
Pairing a frilly white dress with worn-in vintage-inspired boots is a win for us.
Reformation Cleodora Dress
Jeffrey Campbell Reflect Boots
A chic miniskirt with chunky white flip-flops? We’ll be wearing this combo all summer.
BY.DYLN X Revolve Brixton Skirt
ABEO Paseo Thong Sandal
This all-white look screams vacation ready. We especially like the linen shorts styled with polished pointed-toe kitten heels.
Reformation Zoey Linen Shorts
TOTEME Sharp Kitten Heel Slingback Pumps
This outfit has us ready to bring back pedal pushers. For this unexpected combo, it’s the casual capri leggings with fancy flip-flops.
Almina Concept Jersey Pedal Pushers
Steve Madden Tracie Sandals
A whimsical skirt with sporty sneakers on repeat this summer.
Bardot Amorette Cotton Maxi Skirt
adidas Tokyo Shoes
Boxer shorts will define summer 2025, and we love the idea of wearing them with simple ballet flats.
Anthropologie The Wren Boxer Shorts
Schutz Arissa Flats
