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“chukka and Boots” we found 285 items!

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View More Like This Salvatore Ferragamo - Mermaid Boot
Salvatore Ferragamo Mermaid Boot $860.00 Rated: 5 stars!
LUXURY
View More Like This Giorgio Armani - Microhole Chukka Boot
Giorgio Armani Microhole Chukka Boot $595.00
LUXURY
View More Like This Giorgio Armani - Microhole Chukka Boot
Giorgio Armani Microhole Chukka Boot $595.00
LUXURY
View More Like This Salvatore Ferragamo - Lagos Boot
Salvatore Ferragamo Lagos Boot $695.00 $555.99 Rated: 5 stars!
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 HELM Boots - Pete
HELM Boots Pete $495.00
View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
LUXURY
View More Like This Salvatore Ferragamo - Gustavo Boot
Salvatore Ferragamo Gustavo Boot $695.00 $485.99
LUXURY
View More Like This Salvatore Ferragamo - Gustavo Boot
Salvatore Ferragamo Gustavo Boot $695.00 $485.99
LUXURY

View More Like This Aquatalia - Carlos
Aquatalia Carlos $450.00
View More Like This HELM Boots - Garza
HELM Boots Garza $385.00
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 - 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 - 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 Vince - Ramsey Suede Chukka Boot
Vince Ramsey Suede Chukka Boot $375.00
LUXURY
View More Like This Vince - Ramsey Suede Chukka Boot
Vince Ramsey Suede Chukka Boot $375.00
LUXURY
View More Like This rag & bone - Spencer Chukka Lug
rag & bone Spencer Chukka Lug $525.00 $367.99
LUXURY
View More Like This Danner - Mountain Light™ II
Danner Mountain Light™ II $360.00 Rated: 3 stars!

View More Like This Magnanni - Gavin
Magnanni Gavin $350.00 Rated: 5 stars!
View More Like This Frye - Jack Lace Up
Frye Jack Lace Up $348.00 Rated: 3 stars!
View More Like This Frye - Jones Chukka
Frye Jones Chukka $328.00 Rated: 5 stars!
View More Like This Frye - Jones Chukka
Frye Jones Chukka $328.00 Rated: 5 stars!

View More Like This Frye - Jones Chukka
Frye Jones 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 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 Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Vince - Scott
Vince Scott $325.00 Rated: 5 stars!
LUXURY
View More Like This Vince - Scott
Vince Scott $325.00 Rated: 5 stars!
LUXURY
View More Like This Jeffery-West - Trucker Chukka
Jeffery-West Trucker Chukka $318.00
LUXURY

View More Like This Crosby Square - Brogan
Crosby Square Brogan $315.00
View More Like This Chippewa - 5
Chippewa 5" Modern Suburban $309.95 Rated: 5 stars!
Jeffery-West - Sylvian Day Dead
Jeffery-West Sylvian Day Dead $308.00
LUXURY
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00

View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Trask - Gulch 2.0
Trask Gulch 2.0 $295.00 Rated: 5 stars!

View More Like This Zamberlan - Vioz GTX
Zamberlan Vioz GTX $295.00 Rated: 5 stars!
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 Wolverine - 1000 Mile Wesley Wingtip Chukka
Wolverine 1000 Mile Wesley Wingtip Chukka $295.00 Rated: 4 stars!
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 Red Wing Heritage - Foreman Chukka
Red Wing Heritage Foreman Chukka $290.00 Rated: 5 stars!
View More Like This BUGATCHI - Garada Boot
BUGATCHI Garada Boot $285.00
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 - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout 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 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 Frye - Jack Lace Up
Frye Jack Lace Up $348.00 $278.40 Rated: 3 stars!
View More Like This BUGATCHI - San Gimignano Boot
BUGATCHI San Gimignano Boot $275.00
View More Like This Jeffery-West - Laser Chukka
Jeffery-West Laser Chukka $275.00
LUXURY

View More Like This To Boot New York - Curry
To Boot New York Curry $325.00 $259.99
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 Trask - Arlington
Trask Arlington $275.00 $247.99 Rated: 5 stars!

View More Like This Trask - Brady
Trask Brady $245.00 Rated: 5 stars!
View More Like This Chippewa - 5
Chippewa 5" Modern Suburban $309.95 $232.99 Rated: 5 stars!
View More Like This Frye - Joel Brogue Chukka
Frye Joel Brogue Chukka $328.00 $229.99
View More Like This Frye - Joel Brogue Chukka
Frye Joel Brogue Chukka $328.00 $229.99

View More Like This Frye - Jones Chukka
Frye Jones Chukka $328.00 $229.99 Rated: 5 stars!
View More Like This Frye - Jones Chukka
Frye Jones Chukka $328.00 $229.99 Rated: 5 stars!
View More Like This Johnston & Murphy - Garner Cap Toe Boot
Johnston & Murphy Garner Cap Toe Boot $228.00 Rated: 5 stars!
Cole Haan - Zerogrand
Cole Haan Zerogrand $220.00

Cole Haan - Zerogrand
Cole Haan Zerogrand $220.00
View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00
View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00
View More Like This Ted Baker - Torsdi 4
Ted Baker Torsdi 4 $220.00 Rated: 5 stars!

View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 Rated: 4 stars!
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 Rated: 4 stars!
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 Rated: 4 stars!
View More Like This Vasque - Summit GTX
Vasque Summit GTX $219.95 Rated: 4 stars!

View More Like This Chippewa - 5' Modern Suburban Boot
Chippewa 5' Modern Suburban Boot $280.00 $210.99
View More Like This Munro - Sloane
Munro Sloane $210.00 Rated: 4 stars!
View More Like This Munro - Sloane
Munro Sloane $210.00 Rated: 4 stars!
View More Like This BUGATCHI - San Gimignano Boot
BUGATCHI San Gimignano Boot $290.00 $202.99

View More Like This BUGATCHI - San Gimignano Boot
BUGATCHI San Gimignano Boot $290.00 $202.99
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 Rated: 5 stars!
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 Rated: 5 stars!
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 Rated: 5 stars!

View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!
View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!
View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!
View More Like This PARC City Boot - Big Ben
PARC City Boot Big Ben $200.00

View More Like This PARC City Boot - Kensington
PARC City Boot Kensington $200.00
View More Like This Dansko - Jake
Dansko Jake $194.95 Rated: 4 stars!
View More Like This Dansko - Jake
Dansko Jake $194.95 Rated: 4 stars!
View More Like This Trask - Arlington
Trask Arlington $275.00 $192.99 Rated: 5 stars!

View More Like This Trask - Colton
Trask Colton $265.00 $185.99 Rated: 5 stars!
View More Like This Trask - Colton
Trask Colton $265.00 $185.99 Rated: 5 stars!
View More Like This Josef Seibel - Willow 24
Josef Seibel Willow 24 $185.00 Rated: 4 stars!
View More Like This Clarks - Un.Elott Mid
Clarks Un.Elott Mid $180.00