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Chelsea Boots

VAQUERO BOOTS · WESTERN ANKLE FOOTWEAR

Western Chelsea Boots & Short Cowboy Boots

Discover our collection of men's Western Chelsea boots and short cowboy boots, combining traditional Western character with versatile ankle-height designs. Explore genuine leather, suede-inspired nubuck finishes, exotic leathers, and distinctive embossed patterns. From elastic-sided Chelsea styles to convenient zipper boots, find refined Western footwear for everyday wear, casual outfits, and special occasions.

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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)
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)
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
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
Mens Black Square Toe Ankle Boot
White Diamonds Boots
Mens Black Ankle Boots Square Toe Sale price$ 159.99
Brown Square Toe Ankle Boot
White Diamonds Boots
Men's Brown Ankle Boots Square Toe Sale price$ 159.99
Mens Ankle Boots Square Toe
White Diamonds Boots
Men's Tobacco Brown Nubuck Ankle Boots Square Toe Sale price$ 159.99
Light brown Chelsea square toe boot
White Diamonds Boots
Men's Sand Brown Nubuck Ankle Boots Square Toe Sale price$ 159.99
(5.0)
Ariat Men’s Booker Bantamweight Royal Brown Ankle Boot in full-grain leather with broad square toes, elastic side panels, and double-stitched welts.
Ariat
Ariat Men's Booker Royal Brown Square Toe Western Chelsea Boot Sale price$ 149.99
Ariat Booker Ultra Men’s Western Chelsea boot in distressed tan full-grain leather featuring a square toe, elastic side panels, a 1.5-inch stockman heel, and a rubber outsole.
Ariat
Ariat Booker Brown Chelsea Square Toe Boots Sale price$ 149.99
Wild West Men's Honey Square Toe Ankle Boot
Wild West Boots
Men's Honey Ankle Boots Rage Finish Square Toe Sale price$ 169.99
Los Altos men's light brown leather Chelsea square toe western boot on a gray background.
Wild West Boots
Men's Walnut Ankle Boots Square Toe Sale price$ 169.99
VAQUERO BOOTS · WESTERN ANKLE BOOT GUIDE

Explore Western Chelsea Boots & Styles

From elastic-sided Chelsea boots to distinctive Western ankle styles, explore leather finishes, toe shapes, and versatile silhouettes for everyday Western wear.

VERSATILE DESIGN

Chelsea & Slip-On Styles

Traditional Chelsea boots feature elastic side panels for easy on-and-off wear. Explore Western-inspired versions with distinctive leather finishes and toe shapes.

MODERN WESTERN STYLE

Western Zipper Boots

Discover ankle-height Western boots with convenient side zippers, combining classic cowboy-inspired styling with practical entry designs.

LEATHERS & SILHOUETTES

Leather & Toe Shapes

Explore smooth leather, nubuck, and select exotic leather styles. Discover square-toe and rounded-toe silhouettes with distinctive Western finishes.

Whether you're shopping for everyday wear, special occasions, or dress outfits , consider the entry style, leather material, and toe shape. Fit and construction vary by brand and individual model.

Need Help Choosing Your Chelsea Boots?

Compare boot sizes or explore our Western Boot Directory to learn about different leather types, toe shapes, and Western footwear styles.

Cowboy Boot Size Guide → Western Boot Directory →