Skip to search results Skip to filters Skip to sort Skip to selected filters

Leather Chukka Boots

235 items found

Sort By

Your Selections

Search Results

Johnston & Murphy - Copeland Casual Chukka Boot. Color Black Tumbled Full Grain. $175.00. 4.6 out of 5 stars

Clarks - Desert Boot. Color Beeswax 1. $150.00. 4.5 out of 5 stars

Clarks - Wallabee Boot. Color Beeswax. On sale for $84.00. MSRP $170.00.. 4.7 out of 5 stars

Ariat - Lookout. Color Earth/Stone Suede. On sale for $119.96. MSRP $149.95.. 4.2 out of 5 stars

Clarks - Desert Trek. Color Beeswax. $150.00. 4.5 out of 5 stars

Nunn Bush - Luxor Plain Toe Chukka. Color Tan CH. On sale for $69.95. MSRP $100.00.. 4.1 out of 5 stars

Roper - Gum Sticker. Color Desert Tan. $104.99. 5.0 out of 5 stars

Thomas & Vine - Phoenix Chukka Boot. Color Black. $59.99. 1.0 out of 5 stars

Clarks - Bushacre 3. Color Beeswax Leather. On sale for $74.99. MSRP $110.00.. 4.1 out of 5 stars

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $119.95. MSRP $139.95.. 4.3 out of 5 stars

Clarks - Desert Boot Evo. Color Beeswax Leather. $140.00. 3.0 out of 5 stars

Red Wing Heritage - Weekend Chukka. Color Copper Rough & Tough. $239.99. 4.4 out of 5 stars

SOREL - Explorer™ Drift Waterproof. Color Black/Sea Salt. On sale for $101.25. MSRP $135.00.. 4.0 out of 5 stars

Clarks - Eastford Top. Color Dark Brown Leather. On sale for $85.39. MSRP $110.00.. 4.0 out of 5 stars

Florsheim - Lodge Plain Toe Chukka Boot. Color Brown Crazy Horse. $124.95. 4.5 out of 5 stars

Clarks - Morris Peak Waterproof. Color Dark Tan Leather. On sale for $83.35. MSRP $110.00.. 3.7 out of 5 stars

Clarks - Eastford Mid. Color Dark Brown Combination. On sale for $77.25. MSRP $110.00.. 4.2 out of 5 stars

Clarks - Whiddon Mid. Color Waterproof Black Leather. On sale for $84.48. MSRP $110.00.. 3.5 out of 5 stars

TOMS - Navi. Color Water Resistant Black Leather. On sale for $84.00. MSRP $119.95.. 4.1 out of 5 stars

Steve Madden - Jabbar. Color Dark Tan. $99.95. 3.9 out of 5 stars

UGG - Neumel Weather II. Color Grizzly. $159.95. 4.4 out of 5 stars

L.L.Bean - Stonington Chukka Boot Leather. Color Deepest Brown. $129.00. 4.2 out of 5 stars

Twisted X - MDM0033. Color Bomber/Tan. $135.95. 5.0 out of 5 stars

Steve Madden - Harken. Color Cognac Leather. $89.95. 4.1 out of 5 stars

UGG - Neumel Dual Zip II. Color Charcoal. $130.00. 3.7 out of 5 stars

Josef Seibel - Oscar 11. Color Black Oregon/Kombi. On sale for $153.55. MSRP $185.00.. 4.8 out of 5 stars

Deer Stags - Bangor. Color Black/Black. On sale for $49.99. MSRP $100.00.. 4.1 out of 5 stars

Rockport - Total Motion Dressport Chukka. Color British Tan. $139.95. 4.0 out of 5 stars

Johnston & Murphy - Kipton Chukka. Color Brown Oiled Full Grain. $145.00.

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $79.95. MSRP $110.00.. 4.3 out of 5 stars

Nunn Bush - Lancaster Plain Toe Chukka Boot. Color Brown Leather. On sale for $69.95. MSRP $100.00.. 4.4 out of 5 stars

Florsheim - Frenzi Plain Toe Chukka Boot. Color Cognac Smooth/White Sole. $140.00. 5.0 out of 5 stars

Clarks - Rockie 2 Hi. Color Black Leather. On sale for $167.20. MSRP $190.00.. 4.2 out of 5 stars

Cole Haan - Original Grand Chukka. Color Black/Blue. On sale for $137.05. MSRP $180.00.. 4.4 out of 5 stars

Johnston & Murphy - Upton Chukka. Color Tan Oiled Full Grain. $165.00. 2.0 out of 5 stars

Pikolinos - Avila M1T-8011. Color Cuero. $209.95. 4.7 out of 5 stars

Steve Madden - Gantry. Color Tan Leather. On sale for $69.97. MSRP $100.00..

Nunn Bush - Denali Plain Toe Chukka. Color Brown Crazy Horse. $115.00. 4.5 out of 5 stars

Nunn Bush - Otto Plain Toe Chukka Boot. Color Gray. On sale for $59.97. MSRP $90.00..

UGG - Neumel. Color White/White. $149.95. 4.8 out of 5 stars

Rockport - Berenger Plain Toe Chukka. Color Black. On sale for $79.17. MSRP $119.95.. 5.0 out of 5 stars

Twisted X - MDM0019. Color Bomber/Neon Orange. On sale for $103.96. MSRP $129.95.. 4.9 out of 5 stars

Steve Madden - Harken - Extended Sizes. Color Cognac Leather. $95.00. 4.1 out of 5 stars

Pikolinos - Lorca 02N-8080. Color Olmo. On sale for $169.99. MSRP $225.00..

Nunn Bush - Bayridge Plain Toe Chukka Boot. Color Brown CH. On sale for $79.95. MSRP $110.00.. 4.0 out of 5 stars

Rockport - Taylor Waterproof Chukka. Color Black. $129.95. 4.2 out of 5 stars

Twisted X - MDM0016. Color Black. $129.95. 4.0 out of 5 stars

ECCO - St.1 Hybrid Boot GTX. Color Black Cow Leather. On sale for $187.99. MSRP $250.00.. 4.4 out of 5 stars

Propet - Findley. Color Desert Camel. $109.95. 3.7 out of 5 stars

Koolaburra by UGG - Asaiah. Color Chestnut. On sale for $64.95. MSRP $89.99.. 3.0 out of 5 stars

Clarks - RaceLite Wally. Color Black Combi. $130.00.

Eastland 1955 Edition - Seneca. Color Bomber Brown. On sale for $89.99. MSRP $110.00.. 4.4 out of 5 stars

Twisted X - MDM0049. Color Bomber. On sale for $103.96. MSRP $129.95.. 4.0 out of 5 stars

Naot - General. Color Black Water Resistant Leather. $229.95. 4.4 out of 5 stars

Rockport - Style Leader 2 Chukka. Color Black. On sale for $104.96. MSRP $124.95..

Ariat - Spitfire H2O. Color Reliable Brown. $149.95. 4.7 out of 5 stars

Durango - 5" Red Dirt Rebel Chukka Soft Toe. Color Bark Brown. On sale for $107.50. MSRP $125.00.. 4.3 out of 5 stars

Clarks - Bradley Mid. Color Black Tumbled Leather. On sale for $69.99. MSRP $100.00..

New

Twisted X Work - MDMW001. Color Brown. $149.95. 4.1 out of 5 stars

Twisted X - MDM0057. Color Oiled Saddle/Midnight. On sale for $108.76. MSRP $135.95.. 5.0 out of 5 stars

Steve Madden - Hestonn. Color Tan Leather. $89.99. 3.8 out of 5 stars

Nisolo - Everyday Chukka Boot. Color Tobacco. $180.00. 4.5 out of 5 stars

Twisted X - MCA0007. Color Oiled Saddle. $164.95. 3.7 out of 5 stars

Twisted X - MDM0014. Color Copper. On sale for $103.96. MSRP $129.95.. 5.0 out of 5 stars

BOSS - Tunley Desert Boot. Color Midnight Black. On sale for $181.70. MSRP $230.00..

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Black. On sale for $116.25. MSRP $125.00.. 5.0 out of 5 stars

Pikolinos - Avila M1T-8011C1. Color Black. $209.95.

KEEN - Mosey Chukka Leather. Color Dark Olive/Black. On sale for $108.75. MSRP $145.00.. 3.0 out of 5 stars

Steve Madden - Hestonn - Extended Sizes. Color Tan Leather. On sale for $89.99. MSRP $95.00.. 3.9 out of 5 stars

Johnston & Murphy Collection - Jameson Chukka. Color Navy. On sale for $185.99. MSRP $285.00..

Chaco - Paonia Desert Boot. Color Cinnamon Brown. On sale for $112.00. MSRP $140.00..

Blake McKay - Toby. Color Brown. $125.00.

To Boot New York - Dickens. Color Softy Slate. On sale for $257.99. MSRP $395.00..

Ariat - Recon Country. Color Distressed Brown. $149.95. 4.7 out of 5 stars

MARC JOSEPH NEW YORK - Lenox Ave. Color Black Grainy. On sale for $109.95. MSRP $195.00..

Stacy Adams - Tilden Chukka Boot. Color Cocoa. On sale for $69.97. MSRP $119.95.. 3.5 out of 5 stars

SeaVees - Maslon Desert Boot. Color Kona. On sale for $88.62. MSRP $130.00.. 3.4 out of 5 stars

Winthrop - Redwood. Color Brown. $160.00. 5.0 out of 5 stars

Stacy Adams - Cai Chukka Boot. Color Black/Gray. On sale for $72.87. MSRP $99.95.. 5.0 out of 5 stars

Bogs - Classic Casual Chukka. Color Black. $150.00. 4.2 out of 5 stars

Thomas & Vine - Lowry Split Toe Ankle Boot. Color Brown. $119.99.

Caterpillar Casual - Fused Tri Mid. Color Beaned. On sale for $78.75. MSRP $105.00.. 5.0 out of 5 stars

Camper - Wagon - K300378. Color Beige. On sale for $133.87. MSRP $199.00..

New

Marc Fisher LTD - Cooper. Color Dark Gray. $170.00.

Thomas & Vine - Theo. Color Black. $139.99.

Caterpillar Casual - Covert Mid WP. Color Oxblood. On sale for $101.25. MSRP $135.00.. 2.0 out of 5 stars

Bruno Magli - Vicolo Tailored Chukka Leather Boot. Color Cognac. Low Stock. $450.00. 5.0 out of 5 stars

Low stock

MARC JOSEPH NEW YORK - Vestry. Color Brown Napa. $195.00.

Johnston & Murphy - XC Flex Raleigh Chukka. Color Black Full Grain. $175.00.

Born - Brock. Color Brown Distressed Leather. Low Stock. On sale for $112.00. MSRP $140.00.. 4.5 out of 5 stars

Low stock

Roper - Clearcut. Color Brown Vintage Leather. $110.99. 4.8 out of 5 stars

Roper - Siped Outsole Performance Ankle Boot. Color Light Beige. $110.99. 4.3 out of 5 stars

Penny Luck - Visionary Chukka Boot. Color Pecan Brown. $299.00. 5.0 out of 5 stars

Florsheim - Annuity Chukka Boot. Color Burgundy. On sale for $145.99. MSRP $195.00.. 4.5 out of 5 stars

Carlos by Carlos Santana - Corazon Chukka Boot. Color Black Full Grain Calfskin Leather. On sale for $111.30. MSRP $153.95.. 4.3 out of 5 stars

Sandro Moscoloni - Shawn. Color Brown. $199.00.

Steve Madden - Lino. Color Tan Leather. $145.00.

Original Penguin - Canal Chukka. Color Brown Leather. $160.00.

Clarks - Nature 5 Mid. Color Beeswax Combi. $150.00.

New

MARC JOSEPH NEW YORK - Soho Boot. Color Black Grainy Leather. On sale for $129.95. MSRP $195.00..

Sponsored Result. SOREL - Madson™ II Chukka Waterproof. Color Major. $189.95.

Sponsored

These are ads for products you'll find on Zappos.com. Clicking an ad will take you to the product's page.

Sponsored Result. Steve Madden - Gantry. Color Tan Leather. On sale for $69.97. MSRP $100.00..

Sponsored

These are ads for products you'll find on Zappos.com. Clicking an ad will take you to the product's page.

Sponsored Result. Tommy Hilfiger - Gervis2. Color Black. On sale for $89.99. MSRP $105.00..

Sponsored

These are ads for products you'll find on Zappos.com. Clicking an ad will take you to the product's page.

Sponsored Result. Tommy Hilfiger - Gervis2. Color Medium Brown. On sale for $89.99. MSRP $105.00..

Sponsored

These are ads for products you'll find on Zappos.com. Clicking an ad will take you to the product's page.

1 of 3