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Experience the perfect balance of western tradition and modern convenience with our premium leather Chelsea boots and botines. Crafted with signature elastic side panels for an effortless slip-on fit, these ankle boots provide superior comfort from the ranch to the city. Explore our collection of classic silhouettes designed for daily versatility and a timeless style that never goes out of fashion.

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Mens Short Black Western Boots by Hooch
Hooch Boots
Men's Short Black Western Boots Square Toe Sale price$ 169.99
Mens Cowhide Short Cowboy Boots by Hooch
Hooch Boots
Cowhide Short Cowboy Boots Square Toe Sale price$ 169.99
(5.0)
Brown Python Print Short Cowboy Boots
Hooch Boots
Brown Python Print Short Cowboy Boots Square Toe Sale price$ 169.99
Short Black Cowboy Boots
Hooch Boots
Short Black Cowboy Boots Square Toe Sale price$ 169.99
Python Print Ankle Cowboy Boots by Hooch Boots
Hooch Boots
Ankle Cowboy Boots Python Print Square Toe Sale price$ 169.99
(5.0)
Men's Light Brown Short Square Toe Western Boots
Hooch Boots
Men's Light Brown Short Square Toe Western Boots Sale price$ 169.99
Hooch men's black python snake print Chelsea boot square toe profile.
Hooch Boots
Black Python Print Short Cowboy Boots Square Toe Sale price$ 169.99
(5.0)
Pair of men's gray square toe Chelsea boots with brown soles by Quincy on a light gray background.
Quincy Boots
Grey Short Cowboy Boots Square Toe Sale price$ 169.99
Hooch men's light brown Pirarucu fish print square toe Chelsea boot.
Hooch Boots
Men's Brown Pirarucu Fish Print Western Chelsea Boots Square Toe Sale price$ 169.99
(5.0)
Quincy Men's Brown Square Toe Ankle Boot
Quincy Boots
Men's Brown Ankle Boots Square Toe Sale price$ 169.99
(4.0)
Dark Brown Square Toe Ankle Boots - Los Altos Boots
Los Altos Boots
Dark Brown Ankle Boots Square Toe Sale price$ 169.99
Honey Brown Square Toe Ankle Boots - Los Altos Boots
Los Altos Boots
Belmont Honey Brown Ankle Boots Square Toe Sale price$ 169.99
Black Square Toe Ankle Boots - Los Altos Boots
Los Altos Boots
Belmont Black Ankle Boots Square Toe Sale price$ 169.99
Men's Black Ostrich Print Chelsea Square Toe Western Boot
Quincy Boots
Men's Black Ostrich Print Chelsea Western Boots Square Toe Sale price$ 169.99
Quincy men's black leather western Chelsea boot featuring a classic bug stitch on the vamp, a wide square toe, black elastic side goring.
Quincy Boots
Men's Black Square Toe Chelsea Boot Sale price$ 169.99
Quincy Mens Short Caiman Print Boots
Quincy Boots
Mens Short Caiman Print Boots Square Toe Sale price$ 169.99
(4.0)
Brown Petatillo Boot
Hooch Boots
Ankle Braided Boots Square Toe Sale price$ 169.99
Tan Square Toe Ankle Boots - El Canelo
El Canelo
Tan Ankle Boots Square Toe Sale price$ 199.99
Black Square Toe Ankle Boots - El Canelo
El Canelo
Black Ankle Boots Square Toe Sale price$ 199.99
Men's Black Python Print Short Cowboy Boot Square Toe
Quincy Boots
Men's Black Python Print Short Cowboy Boots Square Toe Sale price$ 169.99
(5.0)
Mens Black Suede Boots by Quincy Boots
Quincy Boots
Mens Black Suede Boots Square Toe Sale price$ 169.99
(4.0)
Mens Petatillo Ankle Boot - Besserro
Besserro
Petatillo Ankle Boot Square Toe Sale price$ 169.99
Tan Square Toe Ankle Boots - Quincy Boots
Quincy Boots
Ankle Boots Tan Brown Square Toe Sale price$ 169.99
Quincy Men's Black Suede Chelsea Square Toe Boot
Quincy Boots
Men's Black Suede Chelsea Western Boots Square Toe Sale price$ 169.99
A pair of Ariat men's black Chelsea boots with elastic side panels and pull tabs, shown from a three-quarters angle on a light cream background.
Ariat
Ariat Men's Midtown Rambler Boot Square Toe Sale price$ 169.99
Ariat men's tan leather Chelsea boot with a dark brown elastic side panel and a low dark brown block heel, shown from a side profile on a light beige background.
Ariat
Ariat Men's Booker Almond Brown Square Toe Western Boot Sale price$ 149.99
Short Square Toe Caiman Boots Brown - Los Altos Boots
Los Altos Boots
Short Caiman Boots Brown Square Toe Sale price$ 399.99
Short Square Toe Caiman Boot Black Cherry
Los Altos Boots
Short Caiman Boots Black Cherry Square Toe Sale price$ 399.99
(5.0)
Los Altos men's black genuine caiman belly leather Chelsea ankle boot featuring, black elastic side goring, and a square toe.
Los Altos Boots
Los Altos Men's Black Caiman Belly Chelsea Boots Square Toe Sale price$ 399.99
Los Altos men's Chelsea ankle boot featuring a deep black cherry full quill ostrich leather foot, smooth black leather shaft, and a modern square toe.
Los Altos Boots
Los Altos Men's Black Cherry Ostrich Chelsea Boot Square Toe Sale price$ 399.99
Los Altos men's brown genuine full quill ostrich leather Chelsea ankle boot featuring a square toe, black elastic side goring, and a silver metal star accent.
Los Altos Boots
Los Altos Men's Brown Ostrich Chelsea Boot Square Toe Sale price$ 399.99
Los Altos men's black genuine full quill ostrich leather Chelsea ankle bootsfeaturing a square toe, black elastic side goring, and a leather pull tab.
Los Altos Boots
Los Altos Men's Black Ostrich Chelsea Boot Square Toe Sale price$ 399.99
(5.0)
Quincy Mens Short Caiman Print Square Toe Boot
Quincy Boots
Mens Short Brown Caiman Print Boots Square Toe Sale price$ 169.99
(3.8)
Besserro Square Toe Brown Short Cowboy Boots
Besserro
Brown Short Cowboy Boots Square Toe Sale price$ 169.99
(5.0)
Quincy Chocolate Brown Short Cowboy Boots
Quincy Boots
Chocolate Brown Short Cowboy Boots Square Toe Sale price$ 169.99
Sold outQuincy Square Toe Black Short Cowboy Boots
Quincy Boots
Black Short Cowboy Boots Square Toe Sale price$ 169.99
Los Altos Tan Short Cowboy Boot
Los Altos Boots
Tan Short Cowboy Boots Square Toe Sale price$ 169.99
Brown Short Cowboy Boots
Los Altos Boots
Walnut Brown Short Cowboy Boots Square Toe Sale price$ 169.99
Light Brown Short Cowboy Boot
Los Altos Boots
Light Brown Short Cowboy Boots Square Toe Sale price$ 169.99
(5.0)
Mens Oryx Short Ostrich Print Western Square Toe Boot
Quincy Boots
Mens Short Ostrich Print Western Boots Square Toe Sale price$ 169.99
(5.0)
Quincy Pirarucu Print Short Cowboy Boots
Quincy Boots
Pirarucu Print Short Cowboy Boots Square Toe Sale price$ 169.99
(4.5)
Cuadra Honey Hand Painted Dress Shoe
Cuadra
Cuadra Men's Hand Painted Honey Chelsea Boot Sale price$ 299.99
A pair of tan leather Ariat Chelsea boots with dark brown elastic side panels, shown from a three-quarters angle on a light cream background.
Ariat
Ariat Men's Booker Almond Roca Square Toe Western Boot Sale price$ 149.99
Ariat Men’s Booker Ultra Chelsea square toe boot in brown full-grain leather featuring side elastic panels, traditional toe stitching, and a horseman heel.
Ariat
Ariat Men's Booker Distressed Tan Square Toe Western Boot Sale price$ 149.99
Ariat Booker Ultra Men’s Black Square Toe Western Chelsea Boot in pebbled full-grain leather with elastic side gores, traditional toe stitching, and a Duratread outsole.
Ariat
Ariat Booker Ultra Men's Black Square Toe Boots Sale price$ 149.99
Off-White Square Toe Boots
Quincy Boots
Off-White Boots Square Toe Sale price$ 169.99
Ariat Men’s Hybrid Low Boy Square Toe Cowboy Ankle Boot in Old Earth brown leather featuring elastic side panels, front and back pull tabs, and a grippy rubber outsole.
Ariat
Ariat Men's Hybrid Low Boy Square Toe Boot Sale price$ 159.99
(5.0)
Ariat Men’s Booker Ultra Chukka Boot in black pebbled full-grain leather featuring elastic side panels, a square toe, western stitch detail, and a Duratread outsole.
Ariat
Ariat Men's Booker Ultra Chukka Square Toe Boot Sale price$ 149.99