The Wrong-Shoe Theory Has Gone Feral in NYC, and It's Actually Working

woman wearing matching red set with black boots in nyc summer outfit

(Image credit: @cocoschiffer)

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.

woman wearing mini slip dress with black slip on mules in nyc summer outfit

(Image credit: @fredrika_ekerot)

A summery minidress styled with polished closed-toe heeled mules is an unexpected match, but it works so well.

woman wearing denim shorts with pointed-toe heels in nyc summer outfit

(Image credit: @aniyahmorinia)

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

woman wearing yellow minidress with black clogs and socks in nyc summer outfit

(Image credit: @aishafarida)

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

woman wearing matching red set with black boots in nyc summer outfit

(Image credit: @cocoschiffer)

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

woman wearing white dress with tall boots in nyc summer outfit

(Image credit: @amaka.hamelijnck)

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

woman wearing green miniskirt with chunky white flip flops in nyc summer outfit

(Image credit: @claire_most)

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

woman wearing matching white set with white stiletto heels in nyc summer outfit

(Image credit: @cocoschiffer)

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

woman wearing pedal pushers and fancy flip flops nyc summer outfit

(Image credit: @vikilefevre)

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

woman wearing white maxi skirt with adidas sambas

(Image credit: @poppyalmond)

A whimsical skirt with sporty sneakers on repeat this summer.

woman wearing white boxer shorts with ballet flats summer nyc outfit

(Image credit: @mv.tiangue)

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

This post was published at an earlier date and has since been updated.

Contributing Fashion Editor