Flat Footwear Is the Moment—32 Pairs to Live Your Life in This Winter


(Image credit: @ileniatoma_; Pictured: Maison Margiela Tabi Ballerina Flats ($790))

When even my friends who truly thrive in stilettos are dabbling in loafers, I know I can safely report that there's really something to this flat-footwear trend. I would like to add that it's extremely rude that the internet is suddenly providing all the flat shoes my heart could ever desire—right when I've finally taken it upon myself to cull my footwear down to just a handful of perfect styles. But I digress.

Even if you can't imagine your work wardrobe sans heels, allow me to introduce you to some flat footwear that will (at the very least) keep things chic on your winter commute. From Mary Janes to ballet flats, loafers to slingbacks, metallic styles to sneakers, these 32 pairs just might make you think twice about stealthily changing out of them under your desk.

Glove Flats

Mary Janes

Ballet Flats




Mesh Flats

Cozy Flats

Natalie Cantell
Executive Director, Brand Studio

Natalie leads the style direction for the all content we create in partnership with our friends at various brands plus the legendary team of editors who work on those shoots and stories. She loves collaborating and storytelling, so it's a really fun role for her. It's also the first full-time job she's ever had⁠! She started out in her career as a very mediocre model who agreed to her first styling job to impress a photographer she had a crush on, which led her down a happy path of contributing to Vogue Australia and working as a stylist, fashion writer, and creative director for all sorts of brands and titles. She has a bachelor of communications, but most of her career opportunities came up thanks to some fleeting and accidental street style moments. She's been at Who What Wear for three and a half years and still loves to work as a freelance consultant with brands and designers to shoot their campaigns in NYC. She's originally from New Zealand, and Bondi Beach is her second home, but like just about every other 20-something, she fell in love with New York at some point. She lives in Williamsburg with her fiancé and their weird little dog, Ruby. If you ever need reccies for feel-good fashion, legit coffee spots, politics podcasts, or non-intimidating yoga studios, she's very much your girl.