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“chukka and Black Boots” we found 159 items!

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View More Like This Robert Clergerie - Beeze Boot
Robert Clergerie Beeze Boot $695.00
LUXURY
View More Like This Giorgio Armani - Microhole Chukka Boot
Giorgio Armani Microhole Chukka Boot $595.00
LUXURY
View More Like This rag & bone - Spencer Chukka Lug
rag & bone Spencer Chukka Lug $525.00
LUXURY
View More Like This Stuart Weitzman - Bacari
Stuart Weitzman Bacari $525.00 Rated: 5 stars!

View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
LUXURY
View More Like This HELM Boots - Pete
HELM Boots Pete $495.00
View More Like This Salvatore Ferragamo - Gustavo Boot
Salvatore Ferragamo Gustavo Boot $695.00 $485.99
LUXURY
View More Like This Billy Reid - Indianola
Billy Reid Indianola $395.00
LUXURY

View More Like This Z Zegna - Chukka Grained Calf/Neoprene Boot
Z Zegna Chukka Grained Calf/Neoprene Boot $395.00
LUXURY
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 5 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 5 stars!
View More Like This Frye - Walter Chukka
Frye Walter Chukka $378.00 Rated: 5 stars!

View More Like This Vince - Ramsey Suede Chukka Boot
Vince Ramsey Suede Chukka Boot $375.00
LUXURY
View More Like This Finn Comfort - Linz - 1008
Finn Comfort Linz - 1008 $335.00 Rated: 5 stars!
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!

View More Like This Vince - Gregory
Vince Gregory $325.00
LUXURY
View More Like This Jeffery-West - Trucker Chukka
Jeffery-West Trucker Chukka $318.00
LUXURY
Jeffery-West - Sylvian Day Dead
Jeffery-West Sylvian Day Dead $308.00
LUXURY
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 4 stars!

View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Wolverine - 1000 Mile Wesley Wingtip Chukka
Wolverine 1000 Mile Wesley Wingtip Chukka $295.00 Rated: 4 stars!
View More Like This BUGATCHI - Milano Boot
BUGATCHI Milano Boot $295.00
View More Like This Vince - Marcus Suede Chukka
Vince Marcus Suede Chukka $295.00
LUXURY

View More Like This Vince - Marcus Suede Chukka
Vince Marcus Suede Chukka $295.00
LUXURY
View More Like This BUGATCHI - Garada Boot
BUGATCHI Garada Boot $285.00
View More Like This BUGATCHI - Verona Boot
BUGATCHI Verona Boot $285.00
View More Like This Cole Haan - Original Grand Chukka
Cole Haan Original Grand Chukka $280.00 Rated: 5 stars!

View More Like This Cole Haan - Original Grand Chukka
Cole Haan Original Grand Chukka $280.00 Rated: 5 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars!
View More Like This Frye - Jack Lace Up
Frye Jack Lace Up $348.00 $278.40 Rated: 3 stars!
View More Like This Jeffery-West - Laser Chukka
Jeffery-West Laser Chukka $275.00
LUXURY

View More Like This Trask - Arlington
Trask Arlington $275.00 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $265.00 Rated: 5 stars!
View More Like This Frye - William Monk Chukka
Frye William Monk Chukka $358.00 $250.99
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $249.95 Rated: 4 stars!

View More Like This John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00 $224.99
View More Like This Ted Baker - Torsdi 4
Ted Baker Torsdi 4 $220.00 Rated: 5 stars!
View More Like This Munro - Sloane
Munro Sloane $210.00 Rated: 4 stars!

View More Like This Frye - Phillip Chukka
Frye Phillip Chukka $298.00 $209.99 Rated: 5 stars!
View More Like This Frye - Arden Chukka
Frye Arden Chukka $258.00 $206.00 Rated: 5 stars!
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 Rated: 5 stars!
View More Like This Dansko - Jake
Dansko Jake $194.95 Rated: 5 stars!

View More Like This BOSS Hugo Boss - Pariss Desb by HUGO
BOSS Hugo Boss Pariss Desb by HUGO $275.00 $192.99 Rated: 4 stars!
View More Like This Camper - Beetle Hi-36530
Camper Beetle Hi-36530 $190.00 Rated: 5 stars!
View More Like This Jambu - Tavern
Jambu Tavern $189.00
View More Like This Josef Seibel - Oscar 11
Josef Seibel Oscar 11 $185.00 Rated: 5 stars!

View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Hush Puppies - Waterproof Benson Rigby ICE+
Hush Puppies Waterproof Benson Rigby ICE+ $180.00 Rated: 2 stars!
View More Like This Stacy Adams - Madison II - 65
Stacy Adams Madison II - 65 $180.00 Rated: 4 stars!
View More Like This Clarks - Un.Elott Mid
Clarks Un.Elott Mid $179.95 Rated: 5 stars!

View More Like This Blundstone - BL278
Blundstone BL278 $174.95 Rated: 4 stars!
View More Like This Harley-Davidson - Beau
Harley-Davidson Beau $174.00
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
View More Like This Rockport - Dressports Luxe Waterproof Chukka
Rockport Dressports Luxe Waterproof Chukka $169.95 Rated: 5 stars!

View More Like This Dr. Martens - 1914
Dr. Martens 1914 $165.00 Rated: 4 stars!
View More Like This Wolverine - Cort Waterproof Leather Chukka
Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!
View More Like This Rockport - City Smart - Waterproof Dress Chukka Boot
Rockport City Smart - Waterproof Dress Chukka Boot $159.95 Rated: 3 stars!
View More Like This UGG - Leighton
UGG Leighton $159.95 Rated: 5 stars!

View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!
View More Like This Bogs - Johnny Chukka
Bogs Johnny Chukka $155.00 Rated: 4 stars!
View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00 $154.99 Rated: 4 stars!
View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars!

View More Like This Dunham - REVdash
Dunham REVdash $150.00 Rated: 4 stars!
View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Vince Camuto - Morgen
Vince Camuto Morgen $250.00 $150.00
View More Like This Cole Haan - GrandPro Chukka
Cole Haan GrandPro Chukka $150.00 Rated: 5 stars!
NEW!

View More Like This OluKai - Hamakua
OluKai Hamakua $150.00 Rated: 5 stars!
View More Like This Vivobarefoot - Gobi II M Leather
Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars!
View More Like This Harley-Davidson - Candler
Harley-Davidson Candler $150.00
View More Like This UGG - Freamon HyperWeave
UGG Freamon HyperWeave $149.95 Rated: 5 stars!

View More Like This UGG - Freamon Capra
UGG Freamon Capra $149.95 Rated: 3 stars!
View More Like This Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars!
View More Like This Dr. Martens - 1919
Dr. Martens 1919 $145.00 Rated: 5 stars!
View More Like This Dunham - Johnson Chukka
Dunham Johnson Chukka $145.00 Rated: 4 stars!

View More Like This Lacoste - Laccord Chukka 117 1 Cam
Lacoste Laccord Chukka 117 1 Cam $159.95 $144.99
View More Like This Dr. Martens Work - Ironbridge ST
Dr. Martens Work Ironbridge ST $140.00 Rated: 4 stars!
View More Like This Clarks - Broyd Mid
Clarks Broyd Mid $140.00 Rated: 5 stars!
View More Like This Timberland - Carter Notch Waterproof Plain Toe Chukka
Timberland Carter Notch Waterproof Plain Toe Chukka $140.00 Rated: 4 stars!

View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This Clarks - Wallabee Boot
Clarks Wallabee Boot $139.95 Rated: 5 stars!
View More Like This Sebago - Vershire Chukka
Sebago Vershire Chukka $139.95
View More Like This Sebago - Turner Chukka Waterproof
Sebago Turner Chukka Waterproof $139.95 Rated: 3 stars!

View More Like This Clarks - Wallabee Boot
Clarks Wallabee Boot $139.95 Rated: 5 stars!
View More Like This Clarks - Desert Trek
Clarks Desert Trek $139.95 Rated: 4 stars!
View More Like This Dr. Martens - Diego 7 Tie Lace To Toe Boot
Dr. Martens Diego 7 Tie Lace To Toe Boot $135.00 Rated: 5 stars!
View More Like This SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars!

View More Like This Dr. Martens - 1460 W
Dr. Martens 1460 W $135.00 Rated: 5 stars!
View More Like This Clarks - Stratton Limit
Clarks Stratton Limit $135.00 Rated: 4 stars!
View More Like This Clarks - Wallabee
Clarks Wallabee $134.95 Rated: 5 stars!
View More Like This Timberland - Earthkeepers® Brook Park Chukka
Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 5 stars!

View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!
View More Like This Rockport - Dressports Business Chukka
Rockport Dressports Business Chukka $134.95 $129.95 Rated: 5 stars!
View More Like This UGG - Hendrickson
UGG Hendrickson $129.95 Rated: 5 stars!
View More Like This UGG - Neumel
UGG Neumel $129.95 Rated: 4 stars!

View More Like This Clarks - Desert Boot
Clarks Desert Boot $129.95 Rated: 5 stars!
View More Like This Dr. Martens - 1460 W
Dr. Martens 1460 W $125.00 Rated: 5 stars!
View More Like This Fred Perry - Byron Mid Leather
Fred Perry Byron Mid Leather $125.00 Rated: 3 stars!
View More Like This UGG - Maksim
UGG Maksim $124.95 Rated: 5 stars!