Some shoes earn a permanent spot in the rotation, and for me, classic loafers have been that pair for years. They work with everything I own and quickly became an in-office staple. I’ve worn mine through more busy fashion months with busy walking days than I can count. Lately, though, I’ve noticed the best-dressed people I know swapping their flat pairs for a version with a little lift.
Enter the heeled loafer. It keeps everything we love about the original (the penny strap, the polished leather, the menswear ease) and adds a block or kitten heel that makes even the simplest outfit feel more finished. Don’t worry, your flats aren’t getting retired. This is just the pair I’d buy next. Ahead, see my favorite styles at every price point.
Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.