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.
If you want some more inspo, read on for five boot-and-legging outfits that'll keep your in-between-season outfits in check.
Shop Chic Legging-and-Boot Outfits:
1. Knee-High Boots + Trench Coat + Leggings
Style Notes: A timeless pairing that never fails. Knee-high boots add sophistication to simple leggings, whilst a classic trench coat keeps the outfit polished. This look is perfect for transitional weather and can easily be dressed up or down.
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A structured, lightweight trench that layers effortlessly over leggings.
These high-waisted leggings provide both comfort and a flattering fit.
Sleek chocolate-brown boots that complement the ensemble's cosy elements.
Toteme's minimalist design aesthetic shines in this tote.
These mixed metal earrings are so chic.
2. Riding Boots + Scarf Coat + Leggings
Style Notes: Channel equestrian elegance by combining structured riding boots with a tailored scarf coat and high-waisted leggings. This look is all about remaining grounded in comfort.
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This refined coat featuring an integrated scarf is on everyone's wish list.
A lot for leggings, yes, but these are made from stretch ponte for a close and comfortable fit. They also hit the mid-waist at the perfect place, offering a sleek silhouette.
Classic riding boots crafted from premium leather.
Round-frame sunglasses instantly make an entire outfit that much chicer.
Matching tan tones really solidify this look.
3. Chelsea Boots + Bomber Jacket + Stirrup Leggings
Style Notes: This season, stirrup leggings are having a moment, and the best way to style them is with chunky Chelsea boots and a structured bomber jacket. The juxtaposition of sporty and sleek makes this outfit both practical and fashion-forward.
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A slightly oversized bomber for a modern edge.
The stirrup elastic ensures no pulls or fabric bunching at the top of your boots.
Chunky soles add an effortless cool factor.
We're sticking with the casual, hands-free, errand-day vibe with this look.
Celine sunglasses are iconic.
4. Mini UGG Boots + Blazer + Leggings
Style Notes: The return of mini UGGs has made this look a favourite amongst fashion influencers. Paired with a structured grey blazer and classic leggings, it's the ultimate mix of comfort and structure. The contrast between the soft UGGs and the sharp blazer creates an outfit that feels intentional yet laid-back.
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A versatile blazer you'll get so much wear out of.
This is amongst our editors' favourite white T-shirts to wear under a blazer for a streamlined finish.
A sculpting, high-waisted option that moves with you.
This viral favourite keeps coming back.
The quilting really adds to the off-duty aesthetic.
5. Ankle Boots + Oversized White Shirt + Leggings
Style Notes: If you're after a minimal, polished look, this is the outfit to replicate. An oversized white shirt paired with ankle boots and classic leggings is so Rosie Huntington-Whiteley-coded. Whether worn for a day at the office or a dinner out, this is a fail-safe look.
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Róhe is like a mix of Toteme and The Row, and this crisp white deconstructed shirt proves it.
High-quality leggings from the high street.
A slightly Western-inspired boot from Khaite with a pointed-toe and small slanted heel.
Brown adds richness and polish.
These look more expensive than they are.
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