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: ValentinoGaravani Wool Crepe Jacket ($6300); The Row bag and heels; Leset Rio Stirrup Pants ($200)

Since Jenner is predominantly a denim-wearer for evenings out, this is the first time we've seen her in stirrup leggings styled with heels, but as we head into 2026, we bet it won't be the last. This outfit pairing is an easy way to refresh your winter wardrobe. The two pieces can be worn with any of your favorite sweaters or jackets, making them feel fresh and new again—especially by February, when you've worn them way too many times. And for that thought alone, I'm sold on the look.

Keep scrolling to shop the best black stirrup leggings and pointed-toe kitten heels.

Shop Stirrup Leggings

Splits59

River High Waist Airweight Stirrup Leggings

Every fashion person I know who wears stirrup leggings owns these from Splits59.

Gap

High Rise Double Knit Stirrup Pants

A great affordable option.

Reformation

Needle Leggings

Style with your favorite oversize sweater and wool coat this winter.

Athleta

Transcend High Rise Stirrup Leggings

Wear these with your grippy socks and show everyone at Pilates that you have style.

The exact pair that Jenner just wore.

Lovers and Friends

Penn Pants

If you're looking for a more upscale option to wear at night instead of classic trousers, these are for you.

Shop Kitten Heels

Quince

Italian Leather 55mm Kitten Heel Mules

Since The Row mules that Jenner wore are sold out, I'm grabbing this under-$100 pair that looks designer.

Nordstrom

Liza Slingback Pointed Toe Pumps

These would look elegant with leggings but also with wide-leg jeans, tailored trousers, and maxi dresses.

Schutz

Julie Kitten Heel Mules

The suede makes these look 10x more expensive than they are.

Reformation

Marilyn Wedge Mule

If you want to create a very 2026 outfit, pair your stirrup leggings with these on-trend closed-toe wedge mules.

ZARA

Leather Kitten Heel Shoes

Style with black stirrup leggings and a fitted turtleneck sweater.