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Knee-High Boots 2026: The Chicest Tall Boots for Fall and Winter
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items The chicest knee-high boots for fall and winter 2026, from Gianvito Rossi's equestrian splurge to a $200 Sam Edelman riding boot. Riding boots, a kitten heel, a croc-embossed stiletto and snip toes in the season's best shades: chocolate, espresso, bu...
Inspired by riding boots and traditional saddlery: Italian calfskin in a deep bourgogne, a 70mm heel and an easy pull-on shaft. The splurge that looks like it has been in the family for decades.
Gianvito Rossi Étrier Leather Knee-High Boot in Bourgogne
Khaite's relaxed take on the riding boot, made in Italy from two-toned baby calfskin tumbled for a broken-in feel, with a snip toe and the hint of a stacked heel. Looks inherited, in the best way.
Khaite Colt Knee-High Boot in Vintage Brown Leather
Stretch nappa with a second-skin fit on a tapered kitten heel, inspired by a silhouette first shown on Toteme's Fall Winter 25 runway. The boot that makes a midi skirt look effortless.
Toteme Day Nappa Knee-High Boots in Black
A snip toe and a sculptural block heel on Italian leather in deep ebano brown. A little western, very wearable, and easy to walk in.
Paris Texas Jane Knee-High Boot in Ebano
A slender 85mm stiletto and a sharp pointed toe in croc-embossed leather, in a moody rouge noir. Made in Italy, and made for dinner reservations.
Paris Texas Stiletto Croc-Embossed Knee-High Boot in Rouge Noir
A snipped pointed toe, an angled 85mm block heel and a tall, structured shaft, made in Spain. Stuart Weitzman says wear it with midi skirts or slim trousers, and we agree.
Stuart Weitzman Stassi Knee-High Boot in Black
A block heel and an almond toe on a tall boot in warm elmwood suede. The quiet, polished pair you'll reach for every single day.
Vince Pace Knee-High Boot in Elmwood Suede
Staud's take on the classic riding boot in rich espresso, finished with crescent moon-shaped buckle hardware that matches this season's bags. Riding-boot energy, no horse required.
Staud Harlow Riding Boot in Espresso
Rouje's riding boots in black glazed leather, with a slightly rounded toe, a little gold rose at the ankle and a gold R at the back. Made in Portugal, and very French.
Rouje Edwina Riding Boots in Black Glazed Leather
A pointed toe and a 1" block heel in glossy two-tone syrup leather, sustainably made in Brazil. In Reformation's words: low effort, high reward.
Reformation Dominique Knee Boot in Syrup Leather
Close-fitting burgundy leather with a squared toe, a raised seam down the front and a 7cm cupped heel. Under $400, and the easiest way into the season's favorite color.
& Other Stories Knee-High Leather Boots in Burgundy
Leather inside and out in warm caramel, with a round toe, a stacked heel and a side zip. Madewell's Cloudlift Lite padding makes it the pair you can walk in all day.
Madewell Archival Knee-High Boot in Caramel
A tall leather riding boot in dark brown on a 1.5" heel. The polished $200 classic that works with every coat you own.
Sam Edelman Penny Tall Leather Riding Boot in Dark Brown