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Every so often, we're faced with some tricky fashion questions that have us wanting to phone a friend. Consider our column Ask an Expert that friend, turning to the experts — designers, stylists and other fashion professionals — to address your sartorial thoughts, comments and 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 cushy (and couch-friendly) and our desire for luxury. Over the past few years, we've seen cashmere and sweatpants come together in a plush, relaxed-fit union, but this isn't the wardrobe staple that's taking our outfits to new sophisticated-casual heights. Stirrup leggings are. 

The stretchable, figuring-hugging bottoms that can support us through yoga and round out a polished going-out look have come a long way since their humble equestrian beginnings. With their handy under-sole foot straps, stirrup leggings create an elongated, sleek silhouette and warm the ankles — a win-win for winter dressing. But wearing them outside of the stables or off the exercise mat can get tricky, especially since our most recent examples of them in the fashion space are from the '80s. 

To help turn any stirrup-related sartorial struggle into a triumph, we sought input from someone who epitomizes easy-chic — and who created a best-selling version: Lili Chemla, founder of the Los Angeles-based label Leset

"People are accustomed to a certain level of comfort, but they haven't lost their desire for style," Chemla says. "The stirrup pant is the perfect hero piece for just that." 

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

"I was on a trip in 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 home 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 instance, we were able to elevate a classically utilitarian piece by putting them in our Rio Ponte Fabric from France." 

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

Kitten Heel + Oversized Sweater 

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"I personally love wearing stirrup pants with a small heel to expose the stirrup detail, paired with an oversized sweater, specifically our Zoe Oversized Turtleneck, a chain necklace and a large coat," Chemla says. Other favorites: vintage knits or an Aimé Leon Dore sweatshirt.

Ballet Flat + T-Shirt 

A ballet flat or loafer gives a standard stirrup legging-T-shirt-combo the office-ready polish it deserves. This simple styling hack is ideal for quick workout-to-lunch transitions. If you want to take the morning sweat session look into the evening, you can add a strappy heel and puffer, à la McPherson

Boot or Sneaker + Button Down 


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

"I've always loved a classic Superga, especially with this silhouette because they don't cover too much of the foot, so the stirrup is still very visible," she says. "As for a boot, I'm a big fan of Staud's Palamino boot. With either shoe, I throw on our Margo T-shirt with an oversized button-down." 

Sky-High Heel + Onesie

For a high-impact look, try the chic street-style-approved stirrup unitard. The second-skin garment requires minimal styling and packs a punch paired with a pointed-toe pump. Leset makes a scoop-neck sleeveless version perfect for cold-weather layering, and Skims makes a shimmery catsuit that's the epitome of effortless glam. Chemla recommends pulling the stirrup part under the high heel for a powerful one-and-done statement. 

Shop some of our favorite stirrup leggings, below.

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