Men's Shoes › classic chukka boots

Arlington Chukka Boot

Men's Warfield & Grand Arlington Chukka Boot - Brown - Casual boots Burnished Italian calfskin enriches a classic chukka boot built with cushioned arch support for superior comfort. more

American Eagle Outfitters Shoes | American Eagle Chukka Boots Gray Leather Suede Mens Classic Size 12 | Color: Gray | Size: 12

American Eagle Chukka Boots Gray Leather Suede Mens Classic Size 12 #6921 Grey In Great Condition. Minimal Signs Of Wear. See Photos For Condition As Well. Thank You For Shopping With Me ! more

J. Crew Shoes | J.Crew Bennett Chukka Suede Ankle Boot Men Navy Blue 9.5 Classic Lace Up Shoe | Color: Blue/Tan | Size: 9.5

J.Crew Bennett Chukka Suede Ankle Boot Men Navy Blue 9.5 Classic Lace Up Shoe Size 9.5 Very Good Preowned Condition - Some Minor Scuffing As Shown. Light Marking To Interior Of Both Shoes As Shown. more

J. Crew Shoes | J.Crew Men's 10 Classic Suede Macalister Chukka Boots $148 Navy Blue 79438 | Color: Blue | Size: 10

Very Good Pre-Owned Condition! Slightest Wear To The Suede But Overall Looks Great! Marked A Men's 10. more

Wilcox Plain Toe Chukka Boot - Brown - Thomas & Vine Boots

Men's Thomas & Vine Wilcox Plain Toe Chukka Boot - Brown - Casual boots A classic chukka boot crafted from supple leather brings smart and sophisticated style. more

Leandro Chukka Boot - Brown - Vince Camuto Boots

Men's Vince Camuto Leandro Chukka Boot - Brown - Casual boots Whether it's a casual gathering or a formal meeting, the Leandro Chukka boot from Vince Camuto is a relevant pick. Classic lace-up silhouette with luxe leather upper and light burnished toe... more

Clarks(r) Torhill Hi Chukka Boot - Brown - Clarks Boots

Men's Clarks(r) Torhill Hi Chukka Boot - Brown - Casual boots Creamy suede and soft sheepskin lining enrich a handsome boot in a classic silhouette with a chunky rubber sole. more

Eastland Oscar - Mens 11 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

Eastland Oscar - Mens 11.5 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

Eastland Oscar - Mens 9.5 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

Thomas and Vine Thomas & Vine Aldridge Plain Toe Chukka Boot - Black - 8.5

A look that can hold up in any occasion, the Aldridge by Thomas & Vine. This classic chukka boot offers superior support and comfort with an 8 mm Tru Comfort Foam™ insole and a shock-absorbent XL Extralight® outsole. Distressed genuine leather, a... more

Thomas and Vine Thomas & Vine Aldridge Plain Toe Chukka Boot - Brown - 9.5

A look that can hold up in any occasion, the Aldridge by Thomas & Vine. This classic chukka boot offers superior support and comfort with an 8 mm Tru Comfort Foam™ insole and a shock-absorbent XL Extralight® outsole. Distressed genuine leather, a... more

Thomas and Vine Thomas & Vine Aldridge Plain Toe Chukka Boot - Black - 10

A look that can hold up in any occasion, the Aldridge by Thomas & Vine. This classic chukka boot offers superior support and comfort with an 8 mm Tru Comfort Foam™ insole and a shock-absorbent XL Extralight® outsole. Distressed genuine leather, a... more

Corbin 3-eye Chukka Boot

Men's Stacy Adams Corbin 3-eye Chukka Boot - Brown - Casual boots A classic chukka boot is crafted from supple leather construction offers a casual style when paired with any outfit. more

Manchester Suede Chukka Boot

Men's Blake McKay Manchester Suede Chukka Boot - Brown - Casual boots Supple suede softens the silhouette of a classic chukka boot grounded by a cushioned insole with arch support and a sporty, sneaker-inspired sole. more

Clarks(r) Wallabee Cup Chukka Boot

Men's Clarks(r) Wallabee Cup Chukka Boot - Black - Casual boots Driving shoe-style stitching adds a rustic touch to a classic chukka boot set on a cool crepe-rubber contrast sole. more

Seneca Camp Moc Chukka Boot

Men's Eastland Seneca Camp Moc Chukka Boot - Brown - Casual boots Crafted from premium leather, this classic chukka boot is hand-sewn with a memory foam footbed and slip-resistant outsole for both city and outdoor wear. more

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Brown - Boots A durable crepe rubber sole grounds a classic chukka boot done in a retro checked suede with perforations on the footbed for ventilation. Leather upper and lining/synthetic sole Made in Portugal. more

ugg(r) Neumel Chukka Boot

Men's ugg(r) Neumel Chukka Boot - Gray - Casual boots Naturally breathable UGGpure or UGGplush faux fur lines a classic chukka boot grounded by a lugged sole. Well cushioned, it works well indoors as a slipper, too. UGGpure is a textile made entirely... more

Chandler Chukka Boot

Men's Allen Edmonds Chandler Chukka Boot - Brown - Casual boots Premium, finely napped suede elevates a classic chukka boot handcrafted with a comfortable cork insole, durable bench welt and rubber grip sole. 360o welt construction for durability and... more

Chandler Chukka Boot

Men's Allen Edmonds Chandler Chukka Boot - Brown - Casual boots Premium, finely napped suede elevates a classic chukka boot handcrafted with a comfortable cork insole, durable bench welt and rubber grip sole. 360o welt construction for durability and... more

ugg(r) Neumel Chukka Boot

Men's ugg(r) Neumel Chukka Boot - Brown - Casual boots Naturally breathable UGGpure or UGGplush faux fur lines a classic chukka boot grounded by a lugged sole. Well cushioned, it works well indoors as a slipper, too. UGGpure is a textile made entirely... more

Pebbly Hill Chukka Boot

Men's Rodd & Gunn Pebbly Hill Chukka Boot - Brown - Casual boots A webbed pull tab and two-eyelet lacing provide the minimalist detailing of a classic Chukka boot updated with a luxe leather upper welted to a smart, low-lug sole. Leather upper and... more

Husky Chukka Boot

Men's Warfield & Grand Husky Chukka Boot - Brown - Casual boots Classic chukka styling defines this handsome leather boot furnished with an arch-supporting footbed and set on a slim rubber sole. more

Glide V3 Chukka Slip-on

Men's Peter Millar Glide V3 Chukka Slip-on - Brown - Formal boots A sleek, low profile and an easy-to-wear slip-on silhouette redefine this classic chukka boot. more

Cairngorm Chukka Boot

Men's Barbour Cairngorm Chukka Boot - Black - Casual boots Lightly weathered leather elevates a waterproof chukka boot in a classic silhouette. more

Readhead Chukka Boot

Men's Barbour Readhead Chukka Boot - Purple - Casual boots Burnished leather elevates a versatile chukka boot in a clean, classic silhouette. more

Bushwick Chukka Boot

Men's Anthony Veer Bushwick Chukka Boot - Brown - Casual boots A clean, classic silhouette defines a stylish chukka boot built from rich suede leather. more

Colton Chukka Boot

Men's Blake McKay Colton Chukka Boot - Brown - Casual boots Contrast stitching highlights the classic silhouette of a smooth leather chukka boot grounded by a cushioned, arch-supporting OrthoLite® footbed. more

Readhead Chukka Boot

Men's Barbour Readhead Chukka Boot - Brown - Casual boots Burnished leather elevates a versatile chukka boot in a clean, classic silhouette. more

Vaughn Lace-up Chukka Boot

Men's Vance Co. Vaughn Lace-up Chukka Boot - Gray - Casual boots A faux leather upper adds a smooth, chic style to a lace-up chukka boot shoe for a classic style. more

Otto Plain Toe Chukka Boot

Men's Nunn Bush Otto Plain Toe Chukka Boot - Black - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more

Otto Plain Toe Chukka Boot

Men's Nunn Bush Otto Plain Toe Chukka Boot - Blue - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more

Gomma Chukka Boot

Men's Tod's Gomma Chukka Boot - Brown - Casual boots The brand's monogram is artfully, subtly etched into the suede of this luxurious chukka boot classic in every way but for the pebbled-tread sole. Lace-up style Leather upper and lining/rubber sole... more

Clarks(r) Torhill Hi Chukka Boot

Men's Clarks(r) Torhill Hi Chukka Boot - Blue - Casual boots Creamy suede and soft sheepskin lining enrich a handsome boot in a classic silhouette refreshed in vibrant cobalt blue above a chunky rubber sole. more

Break Chukka Boots

Men's Rockport Break Chukka Boots - Brown - Casual boots The Rockport Classic Break Chukka has versatile style to get you through the day and into the evening. Premium leather or suede uppers. Lace-up closure. Soft knit fabric linings. EVA footbed and... more

Redford Lace-up Chukka Boot

Men's Vance Co. Redford Lace-up Chukka Boot - Brown - Casual boots A faux leather upper adds a smooth, chic style to a lace-up chukka boot for a classic style. more

Otto Plain Toe Chukka Boot

Men's Nunn Bush Otto Plain Toe Chukka Boot - Brown - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more