The wrong shoe never looked so right: Emma Roberts masters summer’s boldest styling trend

Actress Emma Roberts took a daring detour from traditional summer footwear, proving that clunky Oxfords and silky pink separates are a match made in fashion heaven. Her bold style moment brings the “wrong shoe theory” into the spotlight—and it’s cooler than ever. Just when we thought ballet flats and minimalist sandals would dominate another summer of celebrity street style, Emma Roberts stepped out in New York City and flipped the script. Wearing a flirty, ultra-feminine satin set and a pair of chunky, and dare we say, “ugly” shoes, Roberts demonstrated exactly how to master the art of contrast—and why the so-called “wrong shoe theory” may actually be the right choice this season. Her look was a masterclass in playful rebellion: a sugary pink mini skirt and coordinating jacket offset by clunky black Oxfords that injected edge, balance, and pure sartorial intrigue. Whether intentional or instinctual, her styling choice turned heads—and fashion minds—toward this counterintuitive trend that’s all about breaking the rules.

The theory of the “Wrong” shoe

The wrong shoe theory is one of those deceptively simple ideas that packs a powerful fashion punch: pair a look with footwear that feels “off”—the unexpected, the clunky, the disruptive—and suddenly the entire outfit becomes cooler. The goal? Surprise the eye and shift the vibe.

Traditionally, we’re taught to match dainty looks with dainty shoes: floral dresses with ballet flats, tailored pants with sleek heels, mini skirts with sandals. But fashion, in its most compelling form, thrives on friction. The wrong shoe theory leans into that by encouraging a contrast that feels intentional, clever, and rebellious.

For Roberts, that meant sidestepping the obvious choice of pastel pumps or Mary Janes and instead donning Longchamp’s La Voyageuse Derby shoes—a chunky, menswear-inspired pair that delivers pure punk energy beneath her prim pink set. The result? An outfit that refuses to be too sweet or too safe.

From scream queen to street style maven

Roberts’ outfit, snapped while leaving a Longchamp event in NYC, felt like a glamorous nod to her Scream Queens character Chanel Oberlin—only this time, with a grown-up, editorial twist. She wore a pink satin mini skirt with a matching top and a longline jacket, keeping the palette soft and sweet. But her accessories told a different story.

Slung over her shoulder was a black Longchamp Le Roseau XS bag, which Roberts herself described as the “perfect everyday accessory.” Then came the real twist: those thick-soled, statement-making La Voyageuse Derby shoes. The stark black leather sharply contrasted the pastel set, grounding the look with a bit of unexpected grunge.

In her own words, the shoes “bring a bit more edge to the outfit.” And it’s true—without them, the ensemble might have felt too prim. But with them, it was high-low dressing at its best: sophisticated, subversive, and surprisingly wearable.

The rise of the “Ugly” shoe

Roberts isn’t the first to embrace clunky, convention-defying footwear—she’s simply the latest stylish ambassador in a broader movement toward unapologetically “ugly” shoes. From chunky loafers to boat shoes and dad sneakers, fashion’s new favorite footwear leans heavily into comfort, functionality, and boldness.

These menswear-inspired styles have long existed in and out of fashion cycles, but recently, they’ve found fresh favor among trendsetters for their visual tension. Think Prada loafers with mini dresses, Crocs on couture runways, or Birkenstocks at Paris Fashion Week. The wrong shoe theory doesn’t just bend the rules—it’s rewriting them entirely.

And let’s not forget the practicality: shoes like Roberts’s Oxfords are made for all-day wear. Thick soles, supportive structure, and versatility make them ideal companions for modern life, where city walking and spontaneous plans demand more than just pretty heels.

How to get the look (Without the price tag)

While Roberts’s Longchamp pair rings in at $495, there are plenty of more affordable ways to embrace the look. Brands like Coach and Sézane have released similar styles—like the Lyla Platform Derby and Markus Derbies—that offer the same unexpected appeal at a friendlier price point.

But beyond specific brands, the lesson is this: don’t be afraid to mess things up. Throw Oxfords on with a prairie dress. Pair combat boots with a linen romper. Style chunky loafers with your floatiest skirt. The wrong shoe theory isn’t about rebellion for its own sake—it’s about breathing new life into your wardrobe by rethinking balance and contrast. Fashion has always been a playground for paradox. And right now, the boldest, most confident dressers are the ones putting a twist on femininity, juxtaposing softness with strength, sweetness with grit.

Long live the style clash

Emma Roberts’s NYC ensemble might have been just one outfit on one night, but it sent a loud, stylish message: fashion doesn’t always have to make sense. In fact, the best looks often don’t. Whether you’re a seasoned trendsetter or just someone looking to refresh their summer wardrobe, consider reaching for the “wrong” shoes—you may find they’re exactly what your outfit needs. Because sometimes, the boldest step forward begins with a single, unexpected pair of shoes.