This Is the Only Legging Trend Celebs Wear With Heels—Full Stop

By Swedan MargenOctober 24, 2025

I’m not going to lie, when I hear the words “leggings” and “heels” in the same sentence, I can't always get a clear picture in my mind. They just seem contradictory. Love them both in separate contexts, of course; leggings for coziness and heels for a dressy moment. Together? I just wasn’t getting it. Yet, Olivia Culpo, the latest celebrity to endorse a rising legging trend—stirrup leggings—proved it can be an undeniably chic combination.

These leggings aren’t like your average pair; they come with cutouts at the foot, creating a dramatic edge to an outfit that regular leggings just simply can’t do. Culpo’s recent look while out in L.A. is proof. She stepped out in a sleek black pair with an oversized blazer and a knit sweater, cinched at the waist with a simple black belt. To complete the outfit, she wore a pair of classic black slingback pumps (and a mini Hermès Box Kelly Sellier bag). If you want to be stylish and comfortable, then stirrup leggings are the perfect styling trick to accomplish that, as you have the coziness of leggings, but with an elevated twist that’s dressy enough to wear with heels. Even other celebrities like Katie Holmes and Kendall Jenner, who have also paired heels with stirrup leggings, agree.

I have no notes; this look checks all my boxes, and I will be wearing a pair of stirrup leggings with heels for the rest of fall. If you’re into this leggings trend paired with heels, keep scrolling to recreate her look and shop similar items.