The wrong shoe theory is less about wearing something objectively “wrong” and more about disrupting an outfit's predictability. Coined by stylist Allison Bornstein, the idea is wonderfully simple: build your look, then choose the shoe that feels least expected with it. A ballet flat with track pants. A sneaker beneath an otherwise serious maxi dress. A flip-flop with immaculate trousers. The mismatch introduces tension, and tension is often what separates getting dressed from having real style. When every element of an outfit speaks the same language, the result can feel overly resolved—too perfect. The wrong shoe adds an accent.
I’ve become particularly obsessed with the trouser-and-flip-flop version of this equation, largely because the Olsen twins have spent years proving its superiority, and thus inspiring me to abandon my fear of The Great Big New York Dirt. Mary-Kate and Ashley will wear trousers so beautifully cut they practically deserve their own insurance policy, only to let a wafer-thin flip-flop peek out from underneath the hem. On paper, it shouldn’t work. A loafer would be more polished. A pointed pump would elongate the leg. A sleek leather sandal would make far more conventional sense. And yet, the flip-flop is precisely what makes the outfit.
"Wrong Shoe" Flip-Flops
There’s something almost mischievous about wearing an incredibly good trouser with a shoe associated with beaches, pedicures, and taking the trash downstairs. It removes the preciousness from the clothes. Suddenly, the trousers aren’t an occasion; they’re simply what you happen to be wearing while going about your day. It’s the same particular strain of nonchalance the Olsens have perfected elsewhere: enormous designer bags, trailing hems, expensive coats thrown over decidedly unfussy basics. Nothing appears overly orchestrated, even when you know every proportion is exactly right.
On the street-style circuit, other celebrities have started to embrace the flip-flop and all its barely-there glory, from Zoe Kravitz (another The Row obsessive) to Kendall Jenner and Bella Hadid. And, like the Olsens, they go beyond the warm-weather season, too. When paired with a silk bomber, adeptly cut blazer, or overtly pleated trousers, they lean evening—which was as surprising to me as it was to others. If you’re not too confident about it yet, try pairing them with a trouser first—it’s the easiest way to look effortlessly put together.
How I Style It
What brand do you think of when you picture a flip-flop? Of course, it’s the classic Havaianas. Luckily for the fashion set, this beachy, lived-in casual flop comes in square-toe and thinner iterations for variety. If you’re ever in New York during the summer and fall, you’ll see the most stylish women sporting them with everything from trench coats and oversized bags to knitted maxi dresses and suede totes.
For work and a post-office event, I styled mine with a sharp powder blue blazer and camel-colored straight-leg trousers. To keep it workwear appropriate, I layered the blazer over a chic button-down shirt, which can be found everywhere from Zara to J.Crew. For this look, I wanted to embrace the neutral-with-a-pop palette and wore Emme Parsons' coveted Meta sandals, which are a padded pair of croc-embossed chocolate brown flip-flops.
For casual weekends spent with my baby, Row, I like to wander around Brooklyn in an ensemble that works for crawling around the indoor playground, getting a coffee, strolling and daydreaming about brownstones, all while remaining comfortable without sacrificing personal style—every mother’s struggle! Now that it’s fall, I’ve been pulling an Olsen and wearing my oversized funnel-neck jacket with simple black trousers and a classic black flip-flop.
Which brings me to my current position: I don’t think the flip-flop is the compromise shoe anymore. I think it might be the chicest one. Give me a trouser that’s slightly too long, a completely unnecessary amount of fabric, and the thinnest possible flip-flop underneath it. The loafer can stay in the closet. I want the shoe that looks like I forgot to finish getting dressed.