As the temperature drops and the season shifts, it’s time to retire your summer sandals and cozy up to the ultimate winter wardrobe essential: boots. Designers are stepping up, offering an array of designs that combine comfort, warmth, and undeniable style. From classic elegance to bold statement pieces, there’s a pair for every taste and every occasion.
Read also: These 8 Designer Sandals Define Summer 2025
Step confidently into the season with boots that are as functional as they are fashionable—because fall and winter deserve style as bold as the cold.
Hermès - Jumping Boots
Hermès reimagines its iconic Jumping Boot with the Jumping Boot Soft, a subtle evolution of the signature equestrian silhouette. Available in Noir and Marron Moka, it’s priced at $3,175.
Read also: Hermès Just Dropped the Boot of All Boots—And I Had to Have Them
Image courtesy: Hermès
Style
This fresh iteration maintains the classic Kelly-buckle detail and timeless lines but introduces a softer, more flexible calfskin that can be worn high or gently scrunched for a relaxed feel. Honoring Hermès’ equestrian heritage, the design complements both tailored ensembles and casual winter looks.
Fit
Designed with a 14.4-inch upper height, 12.2-inch calf circumference, and a modest 0.8-inch heel, the Jumping Boot Soft is comfortable for all-day wear. For extra durability and grip on wet days, we recommend adding a thin rubber sole, though the soft calfskin shines best in dry conditions.
Louis Vuitton - LV Beaubourg Ankle Boot
Louis Vuitton’s Beaubourg Ankle Boot combines on-trend biker appeal with everyday ease. Available in black smooth calf leather, the LV Beabourg Ankle Boot retails for $2,000.
Image courtesy: Louis Vuitton
Style
Echoing the aptly-named LV Biker bag, the Beaubourg Ankle Boot completes the edgy look. A leather and Monogram-canvas harness strap embossed with the Louis Vuitton signature is accented with a silver-toned chain and studs. Elastic side panels make the boot easy to slip on, while the lightweight micro outsole with contrast stitching adds a modern finish.
Read also: 5 Louis Vuitton Bags You Need to Know About Right Now
Image courtesy: Louis Vuitton
Image courtesy: Louis Vuitton
Fit
With a 1.6-inch (4 cm) heel and platform sole, the Beaubourg Ankle Boot offers comfortable all-day wear. The ankle-height silhouette ensures easy styling, and the elastic side panels provide a snug, flexible fit. Lightweight yet durable, the micro outsole keeps the boot practical for city walking, whatever the weather.
Christian Louboutin - Oxybootie Buckled Ankle Boots
When you’re looking to flash that red sole, Christian Louboutin’s Oxybootie buckled leather ankle boots are a timeless take on biker-style boots with just enough edge. Crafted from smooth leather and retailing for $1,695, this sleek design combines classic Louboutin polish with a touch of attitude.
Image courtesy: Net-a-Porter
Style
The Oxybootie features chunky lug soles and buckled straps that give a subtle biker-inspired look. Rear zips help preserve the boot’s shape over time, making it both functional and fashion-forward. Its ankle-height silhouette pairs effortlessly with skinny jeans, trousers, or skirts for versatile styling options.
Image courtesy: Net-a-Porter
Image courtesy: Net-a-Porter
Fit
The Louboutin Oxybootie fits true to size and is available in both whole and half sizes to help you find your ultimate fit. The ankle-height design and chunky lug sole offer all-day comfort, while the supple leather gradually molds to your foot for a personalized, broken-in feel.
Image courtesy: Net-a-Porter
JW Anderson - Loafer Ankle Boots
More under-the-radar is the brand JW Anderson, named for its founder and designer Jonathan Anderson, who is the new head Creative Director for men’s and women’s Dior. Known for its inventive hybrid designs, the brand’s loafer-inspired ankle boots capture its signature mix of classic and modern style. Available in Black leather or Brown suede, they’re priced at $950.
Read also: Jonathan Anderson’s Dior Debut – Men’s Summer 2026
Image courtesy: Net-a-Porter
Style
These ankle boots merge traditional loafer details with a classic combat boot silhouette. Contrast stitching along the sides adds subtle visual interest, while the smooth leather or soft suede finish ensures versatility. The result is a hybrid style that balances polished elegance with urban edge—ideal for pairing with tailored pants, jeans, or skirts.
Image courtesy: Net-a-Porter
Image courtesy: Net-a-Porter
Fit
The boots fit true to size and are available in whole sizes only. Their ankle-height construction and sturdy sole provide comfortable all-day wear, while the smooth leather or supple suede molds to the foot over time.
Image courtesy: Net-a-Porter
Hermès - Jeff Ankle Boot
If you loved the Jaimy biker boot from Hermès’ Fall-Winter 2024 lineup, you’ll appreciate the Jeff Ankle Boot, which channels a sleek, urban edge while keeping a classic touch of Hermès elegance. Available in Noir calfskin ($2,625) as well as Beige Galet and Brun Fumé suede ($2,250).
Style
The Jeff Ankle Boot balances modern sophistication with timeless design. Featuring the iconic Kelly buckle and a lightly notched sole, it pairs effortlessly with tailored pants, skirts, and dresses. A discreet inner zip allows for easy on-and-off.
Image courtesy: Hermès
Image courtesy: Hermès
Fit
Designed with a 1.4-inch heel and slight platform, the Jeff Ankle Boot offers both comfort and style. Its chunky, notched sole is surprisingly lightweight, making the ankle-height boot easy to wear while providing a flattering fit—ideal for city strolls or dressier occasions.
Jimmy Choo – Rosabel 55 Suede Ankle Boots
Jimmy Choo’s Rosabel 55 ankle boots combine two key trends: suede material and rich chocolate-brown tones. Also available in tan, these boots riff on classic combat styles while adding luxe, modern touches, and retail for $1,250.
Read also: The Chocolate Edit: Must-Have Brown Bags for Winter
Image courtesy: Net-a-Porter
Style
The Rosabel 55 boots feature distinctive tie straps at the cuffs, adding a playful, stylish edge to the classic combat silhouette. Crafted from soft suede, they rest on practical block heels and gripped lug soles, giving both height and stability. Side zips ensure easy on-and-off wear, making them a functional yet fashion-forward choice for fall and winter wardrobes.
Image courtesy: Net-a-Porter
Image courtesy: Net-a-Porter
Fit
These boots fit true to size and are available in full sizes only, with half-size wearers advised to go up to the nearest whole size. The ankle-height design, sturdy block heel, and gripped lug sole provide comfortable all-day wear, while the soft suede molds gently to the foot.
Which of these luxury boots is calling your name this season? Share your pick—and tell us how you’ll be styling your winter walks this year.
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Updated: October 16th, 2025
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