How do I style stirrup leggings?

Every once in a while, we’re faced with tricky fashion questions that make us want to phone a friend. Consider our Ask an Expert This Friend column, turning to the experts — designers, stylists, and other fashion pros — to answer your thoughts, comments, and sartorial concerns.

Our ever-evolving idea of ​​the perfect pant currently sits at the center of a Venn diagram seeking the intersection of our craving for something plush (and couch-friendly) and our desire for luxury. Over the past few years, we’ve seen cashmere and sweatpants come together in a plush, laid-back union, but it’s not the wardrobe essential that takes our outfits to new sophisticated-casual heights. . Stirrup leggings are.

Stretchy, form-fitting bottoms that can support us through yoga and complete a polished outing look have come a long way from their humble equestrian beginnings. With their practical foot straps under the sole, the stirrup leggings create an elongated, elegant silhouette and warm the ankles – a win-win for winter dressing. But wearing them outside the stables or the exercise mat can get tricky, especially since our most recent examples in fashion are from the 80s.

To help turn any stirrup-related sartorial struggle into a triumph, we asked the opinion of someone who epitomizes easy-chic – and who has created a best-selling version: Lili Chemla, founder of the label Leset based in Los Angeles.

“People are used to a certain level of comfort, but they haven’t lost their desire for style,” says Chemla. “The stirrup pants are the perfect hero piece for this.”

Instagram’s It-girls — everyone from Blanca Miró to Tamu McPherson — seem to agree, having sported Leset’s stirrup leggings on several occasions over the past few months. Chemla’s fascination with the silhouette, however, came long before the rise in influencer sightings (or even the pandemic).

“I was on a trip to Antarctica about six years ago, and the only leggings that were warm enough were a pair of stirrup leggings. I continued to wear them when I got back to New York and found them so easy to dress up and down,” she says. “At Leset, we’re always looking for ways to take classic styles and reinterpret them. In this case, we were able to elevate a classic utilitarian piece by putting them in our Rio Ponte fabric from France.”

Ahead, Chemla shares some tips on what to wear with stirrup leggings — and how to dress them up or down.

Small heel + oversized sweater

“I personally like to wear stirrup pants with a small heel to expose the stirrup detail, paired with an oversized sweater, especially our Zoe Oversized Turtlenecka chain necklace and a big coat,” says Chemla. Other favourites: vintage knits or an Aimé Leon Dore sweatshirt.

Ballerina + T-shirt

A ballerina or loafer gives a standard stirrup legging-t-shirt combo the office-ready polish it deserves. This simple style hack is great for quick transitions from workout to lunch. If you want to enjoy the morning sweat session in the evening, you can add a strappy heel and a puff, at the McPherson.

Boot or Sneaker + Button Down


Chemla pairs stirrups with a sneaker or boot for its go-to casual look, depending on the weather.

“I’ve always liked classic Superga’s, especially with this silhouette because they don’t cover the foot too much, so the stirrup is still very visible,” she says. “As for a boot, I’m a huge fan of Staud Palamino Boot. With either shoe, I put on our Margo t-shirt with an oversized button down shirt.”

Sky-High Heel + Onesie

For a high-impact look, try the street style-approved chic stirrup leather. The second-skin garment requires minimal styling and packs a punch paired with a pointed toe pump. Leset makes a sleeveless scoop neck version perfect for cold weather layering, and Skims makes a sparkly jumpsuit it’s the epitome of effortless glamour. Chemla recommends pulling the stirrup portion under the high heel for a powerful and unique statement.

Check out some of our favorite stirrup leggings below.

Please note: we occasionally use affiliate links on our site. This in no way affects our editorial decision-making.

Never miss the latest fashion industry news. Sign up for Fashionista’s daily newsletter.

Comments are closed.