Let’s face it: leggings are a staple we all can’t live without. They’re comfortable, versatile, and ready for just about anything—from lounging to running errands to working out. But just when we thought we’d exhausted every way to style them, enter a fresh pairing that’s rewriting the rulebook: leggings with riding boots. Yes, you read that right. And no offense to our beloved sneakers, but this combo might just be the elevated twist your cold-weather wardrobe’s been waiting for.
The Aspen Effect: Where Style Gets Elevated
While the rest of us were still trying to figure out how to make leggings look less like gymwear and more like streetwear, Kendall Jenner casually dropped the ultimate winter style blueprint during a chic escape to Aspen. She was spotted walking through the snow-dusted streets with Hailey Bieber and Fai Khadra, giving us a look that was anything but après-ski cliché.
Her secret? A sleek pair of Commando Classic Leggings, tucked seamlessly into Ann Demeulemeester’s Nes Riding Boots. The result? Effortless sophistication with a hint of equestrian flair, perfect for the upscale mountain vibes of Colorado’s most stylish town. Whether or not you’re planning a trip to Kemo Sabe, lunching in Betula, or hitting the slopes at Ajax, this look works just as well on city streets as it does in ski towns.
From Sporty to Sophisticated: The Leggings Glow-Up
Leggings have long walked the line between functional and fashionable, but let’s be honest—they tend to lean more athleisure than elegance. That is, until now. With the right styling, they can easily become part of a polished, high-fashion ensemble.
Kendall’s formula is simple but powerful:
- Base Layer: A classic black turtleneck, layered underneath an hourglass-shaped Alaïa blazer. Structured, yet soft.
- Accessories: A brown fur cap for warmth and attitude, sunglasses for mystery, and leather gloves for a refined edge.
- The Finishing Touch: A brown Idaho Tote from The Row, completing the look with understated luxury.
It’s a monochrome base elevated by sharp tailoring and rich textures—proving that leggings don’t need to scream “casual.”
Why Riding Boots Work So Well
Let’s break it down. What makes riding boots the perfect match for leggings?
- Structure Meets Stretch: The stiff leather of a boot plays beautifully against the soft silhouette of leggings, creating visual balance.
- Instant Polish: Unlike sneakers, boots inherently add a sense of formality and purpose.
- Flattering Fit: Tucking leggings into tall boots elongates the legs and streamlines the silhouette.
- Weather-Proof Style: Boots offer the warmth and protection that sneakers can’t always deliver in winter climates.
Plus, riding boots evoke a timeless equestrian feel—think classic, confident, and subtly rebellious.
How to Get the Look (Even if You’re Not in Aspen)
You don’t need to be jetting off to a ski resort or rubbing shoulders with A-listers to recreate the vibe. Here’s how you can adapt the look for everyday wear:
- Leggings: Stick to structured styles with a matte finish like Commando, Spanx, or even faux leather options. You want a legging that holds its shape and doesn’t scream “yoga class.”
- Boots: Opt for classic black or brown riding boots—flat or with a low heel. Look for clean lines, minimal hardware, and high shafts that hit just below the knee.
- Top Layers: A long tailored blazer, a wool coat, or even a belted trench will do wonders. Keep the silhouette crisp.
- Accessories: Think fur-lined hats, oversized sunnies, and a structured tote. Simple, yet statement-making.
The Takeaway: Elevate the Everyday
Kendall’s Aspen-approved outfit shows us that the beauty of leggings lies not just in their comfort, but in their potential. With a little imagination—and the right pair of boots—your coziest pieces can be transformed into something runway-worthy.
So while sneakers will always have a place in our closets, maybe it’s time to make room for their more polished cousin. Because once you’ve tried the leggings-and-riding-boots pairing, you might find yourself leaving the sneakers behind more often than you’d expect.
Now excuse me while I go dust off my boots and pretend I have a coffee date in Aspen.
