Kendall Jenner Has Just Figured Out the Ideal Way to Pair Heels with Leggings in 2026.

      The official countdown to 2026 has begun. Although there are a few weeks left, fashion experts are offering an early glimpse of micro-trends, outfit pairings, and styling tips that fashion-forward individuals will likely adopt and repeat in the upcoming year. One trend features the outfit combination that Kendall Jenner recently wore: stirrup leggings paired with kitten heels. At the OBB holiday party in L.A. last weekend, Jenner was seen in a casual yet festive ensemble. She sported a fur-trimmed knit jacket by Valentino, black stirrup leggings, closed-toe kitten-heel mules, and a red leather shoulder bag from The Row.

      At Who What Wear, we consistently explore stylish ways to wear leggings, whether focusing on legging colors, cuts, or styling methods. A consistent theme in these stories is the idea that leggings can and should be worn beyond gym settings and Pilates classes. They can be dressed up for occasions like holiday parties, and Jenner exemplifies this by styling stirrup leggings—often seen as more elegant and upscale compared to traditional ankle-length pairs—with pointed-toe kitten-heel mules.

      On Kendall Jenner: Valentino Garavani Wool Crepe Jacket (£4300); The Row Liisa Kitten Two Heels (£1020); Leset Rio Stirrup Leggings (£185).

      Since Jenner typically favors denim for her evening outings, this marks the first time we’ve seen her in stirrup leggings styled with heels, but as we approach 2026, it’s unlikely to be the last. This outfit combination offers an effortless way to refresh your winter wardrobe. These two items can easily be paired with any of your favorite sweaters and jackets, giving them a renewed feel—especially by February, when they may have been worn too frequently. For that reason alone, we’re sold on this look.

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

      Shop Stirrup Leggings

      LESET

      Rio Stretch-Ponte Stirrup Leggings

      Every fashion enthusiast we know who wears stirrup leggings owns these from Leset.

      An affordable option.

      Reformation

      Needle Legging

      Pair with your favorite oversized sweater and wool coat this winter.

      lululemon

      Women's Evolution Leg Warmer - Black - S/m

      Wear these with your grippy socks to show off your style at Pilates.

      The Frankie Shop

      Caserta Stirrup Leggings

      The front seam makes these ideal for dressing up.

      If you’re in search of a more refined option for evening wear instead of classic trousers, these are perfect.

      Shop Kitten Heels

      The Row

      Liisa Kitten Two Heel in Leather

      These would look sophisticated with leggings, as well as with wide-leg jeans, tailored pants, and maxi dresses.

      ZARA

      Embossed Slingback Shoes

      This pair under £40 could easily be mistaken for designer.

      MANGO

      Kitten-Heeled Shoes With Ankle Strap

      Pair with black stirrup leggings and a fitted turtleneck sweater.

      For a truly 2026 look, consider combining your stirrup leggings with these trendy peep-toe wedge mules.

      Manolo Blahnik

      Maysale 50 suede mules

      The suede material will add an extra touch of elegance to your leggings.