Boots are the cornerstone of any chilly-day ensemble. From over-the-knee silhouettes to square-toe designs, the cold-weather staple — much like a good winter coat — can make (and never break) an outfit. But the most versatile option? Knee-high boots, hands down. They’re a secret sauce accessory that makes an outfit feel fully styled, with an elevated, slick finish — paired with everything from winter dresses (plus tights!) to your default jeans and prettiest midi skirts.
Whether you lean toward leather or luxe suede, unique stretchy knits or metallic finishes, elegant stilettos or flat lug soles, we’ve rounded up every trending style worth coveting this season. And for those who need a little extra room, we’ve included wide-calf options that don’t skimp on style.
Ahead, you’ll find versatile black knee-high boots perfect for transitioning from day to night, bold animal prints, and cowboy boots to add flair to your 2025 shoe lineup — plus everything in between.
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Leather Knee-High Boots
A classic pair of leather knee-high boots is a wardrobe MVP that only gets better with wear. The sleek styles we’ve picked — think kitten, block and wedge heels — are expertly crafted and well worth the splurge.
J.Crew Stevie Leather Knee-High Pull-On Boots, $, available at J.Crew
Larroudé Milan Block Boot In Wine Leather, $, available at Larroudé
Vagabond Deena Tall Boots, $, available at Vagabond
Ba&sh Heeled Boots, $, available at Ba&sh
Miista Hedy Tall Boots, $, available at SSENSE
Wide-Calf Knee-High Boots
Finding wide-calf boots can be a pain — but that’s why we did the legwork. Brands like Vince Camuto, Naturalizer and Dolce Vita go beyond standard wide calf sizing with options as roomy as 20 inches, while Vivaia’s knit boots stretch to fit with ease.
Vince Camuto Sangeti Extra Wide Calf Boot, $, available at Amazon
Naturalizer Deesha Extra Wide Calf Knee High Boot, $, available at Nordstom
Sam Edelman Sylvia Tall Wide Calf Boots, $, available at Free People
Dolce Vita Raj Wide Calf Boot, $, available at Revolve
Vivaia Knee-High Water Repellent Wool Boots, $, available at Vivaia
Duo Boots Charlotte Knee High Boots in Black Leather, $, available at Duo Boots
Knee-High Cowboy Boots
Western fashion isn’t going anywhere — 2024 proved it, and 2025 is doubling down with even more cowboy boots hitting the streets. If you haven’t tried the Cowboy Carter-approved trend yet, now’s the time to cart a knee-high pair. Whether you go classic or modern, they’ll bring a touch of unexpected flair to your winter wardrobe.
Jeffrey Campbell Finn Tall Western Boots, $, available at Free People
Jigsaw Suede Knee High Western Boot, $, available at Jigsaw
Billini Homestead Wide Calf Boots, $, available at Free People
Ariat Belinda StretchFit Western Boot, $, available at Ariat
Aerosoles Croco Faux Leather Knee High Western Boot, $, available at Aerosoles
Staud Western Wally Boot, $, available at Staud
High Heel Knee-High Boots
Want to strut into the new year with confidence? A pair of heeled boots will do the trick. From sleek stilettos to chunky block and short kitten heels, we’ve got styles to match your vibe — and trending red and metallic options that pack a punch.
Steve Madden Smith Red Leather Fold-Over Boot, $, available at Nordstom
Circus by Sam Edelman Oaklyn Knee High Boot, $, available at Circus by Sam Edelman
Charles & Keith Lace-Up Pointed-Toe Knee-High Boots, $, available at Charles & Keith
Reformation Remy Knee Boot, $, available at Reformation
Zara Metallic Kitten Heel Boots, $, available at Zara
Jeffrey Campbell Checkmate Boots, $, available at Jeffrey Campbell
Knee-High Flat Boots
Looking for a practical, everyday boot? Flat soles are your best bet. Go for a flatform, chunky combat style or classic riding boot — all offering comfort without skimping on style. Pair them with mini dresses, midi skirts, leggings or wide-leg trousers for endless versatility.
Everlane The Riding Boot, $, available at Everlane
Mango Decorative Buckle Leather Boots, $, available at Mango
ASOS DESIGN Carmen Chunky Flat Knee Boots, $, available at ASOS
FitFlop Folded-Knot Flatform Tall Stretch Boots, $, available at FitFlop
Dr Martens Amaayah Hi Leather Women’s Black Boots, $, available at Tower London
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