Not Ballet Flats, Not Slingbacks—Chic New Yorkers Prove This Timeless Shoe Trend Looks Best With Skirts, Jeans, and Dresses
Loafers used to feel like business shoes, something you'd wear when you want to be taken seriously at your 9-to-5. Then Miu Miu happened, as it always does. Once the brand put the shoes on the runway, they started to gain major appeal—not as something you could wear with a blazer but as something you could just wear in general when you want to look cute but also feel comfortable.
Because loafers do have a formal reputation, they give an academic, preppy vibe to any look, but that's part of the fun. You don't have to wear them with pleated skirts and polos. Honestly, most stylish New Yorkers aren't.
Instead they're pairing them with just about everything, from baggy denim to tiered plaid skirts to lacy slip skirts. Loafers look good with everything because they bring a unique aesthetic to anything, and while some items that are traditionally part of a formal uniforms can feel serious, loafers don't. They are scholarly but not in a stuffy way.
If you want to switch up your spring footwear wardrobe, look no further. Loafers have all the comfort and versatility of ballet flats while being a bit more durable with thicker soles that add height. But they also feel more warm weather appropriate than ankle boots and are far more casual than slingbacks. Just do what all the cool New Yorkers are doing and wear them with everything.
Shop the best loafers below.

Tara Gonzalez is a senior fashion and social editor at WhoWhatWear. where she is interested in exploring the intersection of fashion and culture and why we are drawn to wearing the things we wear and what that says about the world we live in. Previously she worked as a senior fashion editor at Harper's Bazaar. When she isn't writing trend deep dives for WWW, she's working on her newsletter on Substack, Cult Classic, which explores the very best fashion in film and television. She has a degree in creative writing from The University of Pennsylvania. She lives in Brooklyn with her boyfriend and pug Bjork, the later of which has a very extensive collection of dog-sized Sandy Liang sweaters.