Kendall Jenner Just Determined the Best Way to Wear Heels With Leggings in 2026

The official countdown to 2026 has started: 16 days. While a few weeks remain, fashion insiders are giving us an early look at micro trends, outfit combinations, and styling tricks that those who put thought into their wardrobe will adopt and wear on repeat in the new year. One trend involves the outfit pairing that Kendall Jenner just wore: stirrup leggings and kitten heels.

While leaving the OBB holiday party in L.A. this past weekend, Jenner was spotted wearing a casual yet festive outfit. She had on Valentino‘s fur-trimmed knit jacket, black stirrup leggings, closed-toe kitten-heel mules, and a red leather shoulder bag from The Row.

Here at Who What Wear, we’re constantly covering chic ways to style leggings, whether it’s focusing on legging color trends, silhouettes, or techniques. The common thread throughout all these stories is that you can and should wear leggings beyond the gym or your Pilates studios. Leggings can be elevated for events like holiday parties, and Jenner demonstrates this perfectly by taking stirrup leggings, a style that’s typically more elegant and expensive-looking than classic ankle-length pairs, and dressing them up with pointed-toe kitten-heel mules.

On Kendall Jenner: Valentino Garavani Wool Crepe Jacket ($6300); The Row bag and heels; Leset Rio Stirrup Pants ($200)