Kendall Jenner Has Just Figured Out the Ideal Way to Style Heels with Leggings in 2026.
The official countdown to 2026 has begun. With just a few weeks to go, fashion insiders are offering a sneak peek at micro-trends, outfit combinations, and styling tips that those who are intentional about their wardrobes will be embracing and rewearing in the upcoming year. One such trend features the outfit combination recently sported by Kendall Jenner: stirrup leggings paired with kitten heels. Over the weekend, as she left the OBB holiday party in L.A., Jenner was seen in a casual yet festive ensemble. She wore a fur-trimmed knit jacket by Valentino, black stirrup leggings, closed-toe kitten-heel mules, and carried a red leather shoulder bag from The Row.
At Who What Wear, we frequently highlight stylish ways to wear leggings, including insights on color trends, silhouettes, and styling techniques. A recurring theme in these discussions is that leggings can, and should, be worn beyond just the gym and Pilates studios. They can be dressed up for occasions such as holiday parties, and Jenner exemplifies this by wearing stirrup leggings, which tend to look more elegant and sophisticated than standard ankle-length varieties, and adding pointed-toe kitten-heel mules for a polished touch.
On Kendall Jenner: Valentino Garavani Wool Crepe Jacket ($6300); The Row bag and heels; Leset Rio Stirrup Pants ($200)
Since Jenner typically opts for denim for her evening outings, this is the first time we've seen her in stirrup leggings styled with heels. However, as we approach 2026, we anticipate it won’t be the last. This outfit combination is an effortless way to rejuvenate your winter wardrobe. Both pieces can be paired with any of your favorite sweaters and jackets, bringing a fresh perspective, especially by February when many outfits have been worn repeatedly. For that reason alone, we are fans of this look.
Continue scrolling to shop the best black stirrup leggings and pointed-toe kitten heels.
Shop Stirrup Leggings:
- Splits59: River High Waist Airweight Stirrup Leggings
Every fashionista we know who wears stirrup leggings has this pair from Splits59.
- Gap: High Rise Double Knit Stirrup Pants
An excellent budget-friendly option.
- Reformation: Needle Leggings
Style these with your go-to oversized sweater and wool coat this winter.
- Athleta: Transcend High Rise Stirrup Leggings
Wear these with your grippy socks to show off your style during Pilates.
- Lovers and Friends: Penn Pants
For those seeking a classy alternative to classic trousers for evening wear, these are perfect.
Shop Kitten Heels:
- Quince: Italian Leather Kitten Heel Mules
Since the The Row mules worn by Jenner are sold out, consider this stylish under-$100 pair that has a designer look.
- Nordstrom: Liza Slingback Pointed Toe Pumps
These would complement leggings as well as wide-leg jeans, tailored trousers, and maxi dresses.
- Schutz: Julie Kitten Heel Mules
The suede material gives these a look that’s far more luxurious than their price suggests.
- Reformation: Marilyn Wedge Mule
For a truly 2026-inspired outfit, pair your stirrup leggings with these fashionable closed-toe wedge mules.
- ZARA: Leather Kitten Heel Shoes
Style these with black stirrup leggings and a fitted turtleneck sweater.
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Kendall Jenner Has Just Figured Out the Ideal Way to Style Heels with Leggings in 2026.
Here’s the secret.