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“chukka and Boots” we found 91 items!

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View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!
View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 Rated: 5 stars!
View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 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 Rockport - Dressports Luxe Waterproof Chukka
Rockport Dressports Luxe Waterproof Chukka $169.95 Rated: 5 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 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 Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars!
View More Like This Giorgio Brutini - Norstern
Giorgio Brutini Norstern $110.00 $87.99
View More Like This Nunn Bush - Nichols Wingtip Chukka Boot
Nunn Bush Nichols Wingtip Chukka Boot $90.00 $72.00 Rated: 3 stars!
View More Like This Clarks - Newkirk Top
Clarks Newkirk Top $135.00 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 Clarks - Broyd Mid
Clarks Broyd Mid $140.00
View More Like This Cycleur de Luxe - Lima
Cycleur de Luxe Lima $185.00 $165.99
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 5 stars!

View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00
View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 $139.99 Rated: 5 stars!
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 5 stars!

View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $220.99 Rated: 5 stars!
View More Like This Clarks - Un.Elott Mid
Clarks Un.Elott Mid $180.00
View More Like This Ben Sherman - Gaston Chukka
Ben Sherman Gaston Chukka $100.00 $89.99
View More Like This Kenneth Cole Reaction - Desert Daze
Kenneth Cole Reaction Desert Daze $89.99

View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00
View More Like This Ariat - Henley
Ariat Henley $129.95
View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $170.99 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $245.00 Rated: 5 stars!

View More Like This Gordon Rush - Dawson
Gordon Rush Dawson $245.00 $170.99
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Stacy Adams - Delaney Chukka Boot
Stacy Adams Delaney Chukka Boot $105.00 $74.99 Rated: 4 stars!
View More Like This Clarks - Un.Elott Mid
Clarks Un.Elott Mid $180.00

View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Ariat - Henley
Ariat Henley $129.95
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Calvin Klein - Jae
Calvin Klein Jae $140.00 $97.99 Rated: 4 stars!

View More Like This PARC City Boot - Central
PARC City Boot Central $200.00 $139.99 Rated: 4 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 Frye - Jones Chukka
Frye Jones Chukka $328.00 $229.99 Rated: 5 stars!
View More Like This Stacy Adams - Burgess Cap Toe Chukka Boot
Stacy Adams Burgess Cap Toe Chukka Boot $105.00 Rated: 4 stars!

Messico - Oriol
Messico Oriol $139.00 $97.99 Rated: 5 stars!
View More Like This Kenneth Cole Reaction - Desert Daze
Kenneth Cole Reaction Desert Daze $89.99
View More Like This Clarks - Broyd Mid
Clarks Broyd Mid $140.00
View More Like This Wolverine - Hensel
Wolverine Hensel $195.00 Rated: 4 stars!

View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $170.99 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 Ben Sherman - Gaston Chukka
Ben Sherman Gaston Chukka $100.00 $69.99
View More Like This Kenneth Cole Reaction - Desert Daze
Kenneth Cole Reaction Desert Daze $89.99

View More Like This Grenson - Marcus Suede Chukka Boot
Grenson Marcus Suede Chukka Boot $370.00
LUXURY
View More Like This Nunn Bush - Nichols Wingtip Chukka Boot
Nunn Bush Nichols Wingtip Chukka Boot $90.00 $72.00 Rated: 3 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 Rated: 5 stars!
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 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 Messico - Oliver
Messico Oliver $129.00 $90.99
Messico - Oriol
Messico Oriol $139.00 Rated: 5 stars!
View More Like This Gordon Rush - Dawson
Gordon Rush Dawson $245.00 $170.99

View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
LUXURY
View More Like This Base London - Morris
Base London Morris $140.00 $97.99
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00
View More Like This Jeffery-West - Trucker Chukka
Jeffery-West Trucker Chukka $318.00
LUXURY

View More Like This Stacy Adams - Burgess Cap Toe Chukka Boot
Stacy Adams Burgess Cap Toe Chukka Boot $105.00 $74.99 Rated: 4 stars!
View More Like This Vince - Alberto
Vince Alberto $395.00
LUXURY
View More Like This Spring Step - Efisio
Spring Step Efisio $139.99 Rated: 5 stars!
View More Like This Frye - Sam Chukka
Frye Sam Chukka $298.00

Jeffery-West - Sylvian Day Dead
Jeffery-West Sylvian Day Dead $308.00
LUXURY
View More Like This Ted Baker - Torsdi 4
Ted Baker Torsdi 4 $220.00 Rated: 5 stars!
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 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 - Weston Chukka
Frye Weston Chukka $378.00 Rated: 5 stars!
View More Like This Frye - Will Chukka
Frye Will Chukka $328.00 Rated: 5 stars!
View More Like This Stacy Adams - Madison II Chukka Boot
Stacy Adams Madison II Chukka Boot $180.00

View More Like This Messico - Oliver
Messico Oliver $129.00
View More Like This rag & bone - Spencer Chukka Lug
rag & bone Spencer Chukka Lug $525.00
LUXURY
View More Like This Frye - Jones Chukka
Frye Jones Chukka $328.00 $229.99 Rated: 5 stars!
View More Like This Crosby Square - Brogan
Crosby Square Brogan $315.00

View More Like This Sebago - Collier Chukka
Sebago Collier Chukka $175.00
View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!
View More Like This rag & bone - Spencer Chukka
rag & bone Spencer Chukka $495.00
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 Bruno Magli - Tristin
Bruno Magli Tristin $450.00
View More Like This Bruno Magli - Tristin
Bruno Magli Tristin $450.00
View More Like This Frye - Weston Chukka
Frye Weston Chukka $378.00 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 Grenson - Marcus Suede Chukka Boot
Grenson Marcus Suede Chukka Boot $370.00
LUXURY

View More Like This PARC City Boot - Kensington
PARC City Boot Kensington $200.00
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 Billy Reid - Indianola
Billy Reid Indianola $395.00
LUXURY