It’s that time of year again: to start trying to figure out what shoes to wear with leggings beyond our trusty athletic sneakers. The stretchy bottoms have always been a main character when it comes to cozy weekend looks, but they’re capable of so much more. Luckily, the fall-winter 2026 fashion trends offer us a chance to put that to the test. The sign of a true well-dressed women? Someone who can turn her best leggings, no matter how practical they may be, and turn them into an outfit that’s chic as hell.
So, yes, it’s time to review our options and figure out which shoes go best with leggings. Whether it’s an heeled sandal in a bold color, the trendiest boot of the season, or ballet flats with lots of versatility, there are several options this season that can transform a leggings outfit from meh to something super stylish without losing an ounce of comfort.
Keep scrolling to see what shoes to wear with leggings in fall 2026.
With Almond-Toe Black Pumps
One spectacularly easy way to style leggings this fall? Go with a pair of sleek almond-toe pumps to visually lengthen the legs and instantly elevate a look. Add a tailored blazer over a turtleneck for a retro look that feels reminiscent, in a good way, of Fran Fine in The Nanny. These heels can also be a good alternative to loafers, as they’ll dress up a classic button-down shirt to feel more intentional.
