“chukka and Boots” we found 516 items!

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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 rag & bone - Spencer Chukka Lug rag & bone Spencer Chukka Lug $525.00 LUXURY View More Like This rag & bone - Spencer Chukka Lug rag & bone Spencer Chukka Lug $525.00 LUXURY
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 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 Vince - Alberto Vince Alberto $395.00 LUXURY View More Like This To Boot New York - Clemmons To Boot New York Clemmons $395.00 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 - 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!
Frye - Weston Chukka Frye Weston Chukka $378.00 Rated: 5 stars! NEW! 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 Grenson - Marcus Suede Chukka Boot Grenson Marcus Suede Chukka Boot $370.00 LUXURY
View More Like This Grenson - Marcus Suede Chukka Boot Grenson Marcus Suede Chukka Boot $370.00 LUXURY View More Like This Aquatalia - Alec Aquatalia Alec $350.00 NEW! View More Like This Frye - Will Chukka Frye Will Chukka $328.00 Frye - Jones Chukka Frye Jones Chukka $328.00 Rated: 5 stars! NEW!
View More Like This Frye - Will Chukka Frye Will Chukka $328.00 View More Like This Frye - Jones Chukka Frye Jones Chukka $328.00 Rated: 5 stars! NEW! View More Like This Frye - Jones Chukka Frye Jones Chukka $328.00 Rated: 5 stars! NEW! View More Like This Frye - Will Chukka Frye Will Chukka $328.00
View More Like This Frye - Will Chukka Frye Will Chukka $328.00 View More Like This Vince - Scott Vince Scott $325.00 Rated: 5 stars! LUXURY View More Like This Vince - Gregory Vince Gregory $325.00 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 Jeffery-West - Sylvian Day Dead Jeffery-West Sylvian Day Dead $308.00 LUXURY View More Like This BUGATCHI - Milano Boot BUGATCHI Milano Boot $295.00
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 Red Wing Heritage - Foreman Chukka Red Wing Heritage Foreman Chukka $290.00 Rated: 5 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 - Verona Boot BUGATCHI Verona Boot $285.00 View More Like This BUGATCHI - Garada Boot BUGATCHI Garada 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 - Original Grand Chukka Cole Haan Original Grand Chukka $280.00 Rated: 5 stars! View More Like This BOSS Hugo Boss - Pariss Desb by HUGO BOSS Hugo Boss Pariss Desb by HUGO $275.00 Rated: 4 stars!
View More Like This BOSS Hugo Boss - Pariss Desb by HUGO BOSS Hugo Boss Pariss Desb by HUGO $275.00 Rated: 4 stars! View More Like This Trask - Arlington Trask Arlington $275.00 Rated: 5 stars! View More Like This Trask - Lawson Trask Lawson $275.00 View More Like This Trask - Arlington Trask Arlington $275.00 Rated: 5 stars!
View More Like This Frye - Mark Chukka Frye Mark Chukka $298.00 $267.99 Rated: 4 stars! View More Like This Frye - Mark Chukka Frye Mark Chukka $298.00 $267.99 Rated: 4 stars! View More Like This Trask - Colton Trask Colton $265.00 Rated: 5 stars! View More Like This Trask - Colton Trask Colton $265.00 Rated: 5 stars!
View More Like This Frye - Weston Chukka Frye Weston Chukka $378.00 $264.99 Rated: 5 stars! View More Like This Ted Baker - Azzlan Ted Baker Azzlan $245.00 Rated: 5 stars! View More Like This Ted Baker - Azzlan Ted Baker Azzlan $245.00 Rated: 5 stars! View More Like This Ted Baker - Azzlan Ted Baker Azzlan $245.00 Rated: 5 stars!
View More Like This Trask - Brady Trask Brady $245.00 Rated: 5 stars! Gordon Rush - Dawson Gordon Rush Dawson $245.00 NEW! Gordon Rush - Dawson Gordon Rush Dawson $245.00 NEW! View More Like This Frye - Freeman Chukka Frye Freeman Chukka $348.00 $244.99
View More Like This Frye - Freeman Chukka Frye Freeman Chukka $348.00 $244.99 View More Like This Frye - Joel Chukka Frye Joel Chukka $298.00 $238.40 View More Like This Frye - Luke Wingtip Chukka Frye Luke Wingtip Chukka $298.00 $238.00 Rated: 3 stars! View More Like This Trask - Irving Trask Irving $295.00 $235.99
View More Like This Trask - Irving Trask Irving $295.00 $235.99 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! View More Like This John Varvatos - Brooklyn Chukka John Varvatos Brooklyn Chukka $228.00 NEW! View More Like This To Boot New York - Curry To Boot New York Curry $325.00 $227.99
View More Like This Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00 Rated: 5 stars! 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 Vasque - Summit GTX Vasque Summit GTX $219.95 Rated: 4 stars!
View More Like This Chippewa - Handswen Casual Chukka Chippewa Handswen Casual Chukka $265.95 $212.99 View More Like This ECCO - Jeremy Hybrid Boot ECCO Jeremy Hybrid Boot $210.00 Rated: 4 stars! View More Like This Frye - Mark Chukka Frye Mark Chukka $298.00 $209.99 Rated: 4 stars! View More Like This Frye - Mark Chukka Frye Mark Chukka $298.00 $209.99 Rated: 4 stars!
View More Like This Frye - Arden Chukka Frye Arden Chukka $258.00 $206.00 Rated: 5 stars! View More Like This Frye - Arden Chukka Frye Arden Chukka $258.00 $206.00 Rated: 5 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 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 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 Tommy Bahama - Fane Tommy Bahama Fane $198.00 Rated: 5 stars! View More Like This Lacoste - Montbard Chukka 316 1 Lacoste Montbard Chukka 316 1 $219.95 $197.99
View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 $196.00 Rated: 5 stars! View More Like This Cole Haan - Zerogrand Stitchout Chukka Cole Haan Zerogrand Stitchout Chukka $280.00 $196.00 Rated: 5 stars! View More Like This Gordon Rush - Hansen Gordon Rush Hansen $245.00 $195.99 View More Like This Wolverine - Hensel Wolverine Hensel $195.00 Rated: 4 stars! NEW!