Hold the Sneakers: *This* Is the Stylish Shoe Trend Fashion People Are Wearing with Leggings to Pilates

In the fashion world, certain pairings have become practically second nature, like leggings and sneakers. Chances are, if you're throwing on leggings for a Pilates class or a grocery run, you're slipping into your go-to sneakers without a second thought. But it's time to rethink that habit. A fresh shoe pairing is making waves among the style set: flip-flops.

Take Kendall Jenner, for example. While out and about in L.A. last week, she was spotted in a casual yet chic ensemble: a cropped tank, a zip-up sweatshirt, The Row’s Marlo bag, and leggings. But instead of finishing the look with the expected sneakers, she opted for minimalist thong sandals from The Row. Her choice may seem surprising initially, but given her status as a style icon, you can bet it was intentional—and on trend.

On Kendall Jenner: The Row City Flip Flops ($890); The Row Marlo Bag ($5800)

Elevated flip-flops like hers have quickly become the It summer shoe trend. We've already seen them worn with wide-leg jeans, sundresses, and shorts. Now, Jenner is making a strong case for styling them with leggings, adding another layer to their versatility.

So, if you’ve considered adding a pair to your wardrobe, now’s the time to act. The longer you wait, the fewer options you’ll have. Keep scrolling to shop Jenner’s favorite flip-flops and discover other equally chic styles.

Shop the Best Flip-Flops

Universal Thread

Sherry Thong Flip Flops

Seriously, you can't beat this $20 price for elevated leather flip-flops.

The exact pair Jenner styled with leggings.

Reformation

Jessie Thong Sandals

H&M

Espadrille Flip-Flops

H&M just dropped these new flip-flops with a woven footbed—so chic.

A.EMERY

Kinto Leather Flip Flops

J.Crew

Wide Thong Sandals

Senior Fashion Editor Eliza Huber owns these, and I was shocked when she told me they're from J.Crew. They look so luxe.

Toteme

Croc-Effect Leather Thong Sandals

Every fashion person with good taste has these sandals on their wishlist.

TKEES

Lily Square Toe Flip Flop

The square-toe feels very 2025.

Free People

Sona Thong Sandals

These also come in blue, yellow, red, and brown.