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, femme dress suddenly feels less precious with a clunky loafer anchoring it. A pair of boxers (yes, actual boxer shorts) becomes elevated with the addition of a sleek knee-high boot. And 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? It’s easy. You don’t need a whole new wardrobe—just a fresh perspective. That pair of dainty ballet flats? Try them with cargo pants. Your chunkiest boots? Wear them with something silk and lacy. It’s all about the mix, the tension, and the attitude. The wrong shoe 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 fall under 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.

It’s the denim cutoff shorts with fancy pointed-toe heels here.

A dainty dress with chunky clogs? We’re into it.

This is how you style a midi skirt with mid-calf leather boots.

Pairing a frilly white dress with worn-in vintage-inspired boots is a win for us.

A chic miniskirt with chunky white flip-flops? We’ll be wearing this combo all summer.

This all-white look screams vacation-ready. We especially like the linen shorts styled with polished pointed-toe kitten heels.

This outfit makes us ready to bring back pedal pushers. For this unexpected combo, it’s the casual capri leggings with fancy flip-flops duo.

A whimsical skirt with sporty sneakers on repeat this summer.

Boxer shorts will define summer 2025, and we love the idea of wearing them with simple ballet flats.