5 Legging-and-Boot Outfit Ideas We’re Looking to Add to Our Mood Boards

As a millennial, I have a long history with leggings. In the early 2000s, they were a casual staple, often paired with ballet flats, oversized tunics or—dare I say it—UGGs.

Whilst they may have faded into the background for a few years, leggings are back in full force, and this time, fashion insiders are styling them in much more elevated ways. The key to chic styling? The perfect pair of boots.

I’ve seen it everywhere—at home in London as well as in Paris on a recent trip. From what I’ve witnessed in London, fashion editors and influencers are going very streamlined and classic, with tailored coats and leather knee-high boots paired with sleek leggings. Meanwhile, in Paris, the looks feel a little more nonchalant—stirrup leggings are being styled with Chelsea boots and even bomber jackets, which appear effortless and understated (the objective of the French-girl aesthetic). Whether worn for a coffee run or a night out, it’s clear that this combination is a go-to formula for fashion people right now.

This season, designers have embraced the legging-and-boot duo in fresh and modern ways. The spring/summer 2025 runways saw Bottega Veneta showcase leather leggings tucked into knee-high boots, reinforcing the idea that the comfy basic can be just as polished as tailored trousers. Meanwhile, Max Mara leaned into the power of an oversized coat paired with sleek ankle boots and high-waisted leggings, proving that this once-casual staple can now work across multiple aesthetics.

I’ve always gravitated towards the effortless appeal of leggings, particularly when styled with knee-high riding boots and an oversized jumper—a look I return to year after year. But recently, I’ve been drawn to alternative boot styles including pointed toes and heeled ankle boots that give leggings a more sophisticated feel. Whilst UGGs and ankle boots have long been classic partners for leggings—particularly in the early-mid ’00s—it’s the rise of structured styles—such as sharp pointed-toe ankle boots and the aforementioned polished leather knee-highs—that’s solidifying this combination as a go-to for stylish dressers.

The beauty of leggings lies in their versatility (and comfort, of course). Whether you’re aiming for a polished office look or a relaxed weekend outfit, leggings and the right boots is such an easy and chic option. Hailey Bieber and Rosie Huntington-Whiteley are firm fans of the combo, often spotted in legging looks—a fitted turtleneck with black knee-high or sleek kitten-heel boots is a go-to for both—showcasing the timelessness and ease of the pairing and underscoring how effectively leggings create a streamlined silhouette.