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

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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

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

LPA, Giulia Mini Dress

LPA Giulia Mini Dress

Gia Borghini Abella Pumps

Gia Borghini Abella Pumps

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

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

Cutoff Carpenter Denim Shorts

Good American Cutoff Carpenter Denim Shorts

Noreen Slingback Pump

Reformation Noreen Slingback Pump

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

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

Somebody to Love Mini Dress

Free People Somebody to Love Mini Dress

Bailey Platform Mule

Naturalizer Bailey Platform Mules

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

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

Stretch Midi Skirt

ZARA Stretch Midi Skirt

Cara Boots

Zadig&Voltaire Cara Boots

woman wearing white dress with tall boots in nyc summer outfit

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

Cleodora Dress

Reformation Cleodora Dress

Reflect Boots

Jeffrey Campbell Reflect Boots

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

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

X Revolve Brixton Skirt

BY.DYLN X Revolve Brixton Skirt

Paseo Thong Sandal

ABEO Paseo Thong Sandal

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

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

Zoey Linen Short

Reformation Zoey Linen Shorts

Sharp Kitten Heel Slingback Pump

TOTEME Sharp Kitten Heel Slingback Pumps

woman wearing pedal pushers and fancy flip flops nyc summer outfit

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

Jersey Pedal Pusher

Almina Concept Jersey Pedal Pushers

Tracie Sandal

Steve Madden Tracie Sandals

woman wearing white maxi skirt with adidas sambas

A whimsical skirt with sporty sneakers on repeat this summer.

Amorette Cotton Maxi Skirt

Bardot Amorette Cotton Maxi Skirt

Tokyo Shoes

adidas Tokyo Shoes

woman wearing white boxer shorts with ballet flats summer nyc outfit

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

The Wren Boxer Shorts by Anthropologie

Anthropologie The Wren Boxer Shorts

Schutz Arissa Flats

Schutz Arissa Flats

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