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“chukka and Boots” we found 147 items!

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View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $199.95 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 - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!
View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $199.95 Rated: 5 stars!

View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $199.95 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $245.00 Rated: 5 stars!
View More Like This Spring Step - Efisio
Spring Step Efisio $139.99 Rated: 5 stars!
View More Like This Wolverine - Francisco Chukka
Wolverine Francisco Chukka $180.00 $144.99 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 Dr. Martens - Mayport 2-Eye Desert Boot
Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars!
View More Like This Dr. Martens - Mayport 2-Eye Desert Boot
Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars!
View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $170.99 Rated: 5 stars!

View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $220.99 Rated: 5 stars!
View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 $220.99 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $245.00 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $265.00 Rated: 5 stars!

View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 5 stars!
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 5 stars!
View More Like This Frye - Mark Chukka
Frye Mark Chukka $298.00 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $265.00 Rated: 5 stars!

View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 Rated: 5 stars!
View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $200.00 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 - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!

View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!
View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!
View More Like This Mark Nason - Briggs
Mark Nason Briggs $120.00 Rated: 5 stars!
View More Like This Mark Nason - Briggs
Mark Nason Briggs $120.00 Rated: 5 stars!

View More Like This Frye - James Lug Chukka Shearling
Frye James Lug Chukka Shearling $388.00 $310.40 Rated: 5 stars!
View More Like This Trask - Brady
Trask Brady $265.00 Rated: 5 stars!
View More Like This Wolverine - Orville Desert Boot
Wolverine Orville Desert Boot $165.00 Rated: 5 stars!
View More Like This Wolverine - Orville Desert Boot
Wolverine Orville Desert Boot $165.00 Rated: 5 stars!

Messico - Oriol
Messico Oriol $139.00 $97.99 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 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 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 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 - Weston Chukka
Frye Weston Chukka $378.00 Rated: 5 stars!

View More Like This Giorgio Brutini - Arlo
Giorgio Brutini Arlo $90.00 $80.99 Rated: 5 stars!
View More Like This Giorgio Brutini - Arlo
Giorgio Brutini Arlo $90.00 Rated: 5 stars!
View More Like This Magnanni - Gavin
Magnanni Gavin $350.00 Rated: 5 stars!
View More Like This Josef Seibel - Sienna 03
Josef Seibel Sienna 03 $160.00 Rated: 5 stars!

View More Like This Josef Seibel - Sienna 03
Josef Seibel Sienna 03 $160.00 Rated: 5 stars!
View More Like This Josef Seibel - Sienna 03
Josef Seibel Sienna 03 $160.00 Rated: 5 stars!
View More Like This Josef Seibel - Sienna 03
Josef Seibel Sienna 03 $160.00 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 - 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 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 Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 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 Clarks - Newkirk Top
Clarks Newkirk Top $135.00 Rated: 5 stars!
Messico - Oriol
Messico Oriol $139.00 Rated: 5 stars!
View More Like This Massimo Matteo - 3-Eye Chukka
Massimo Matteo 3-Eye Chukka $169.00 Rated: 5 stars!

View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 Rated: 4 stars!
View More Like This Ted Baker - Torsdi 2
Ted Baker Torsdi 2 $220.00 Rated: 4 stars!
View More Like This Bed Stu - Abel
Bed Stu Abel $175.00 $122.99 Rated: 4 stars!
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 Rated: 4 stars!

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 PARC City Boot - Central
PARC City Boot Central $200.00 $139.99 Rated: 4 stars!
View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $64.95 Rated: 4 stars!

View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $69.95 Rated: 4 stars!
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $249.95 Rated: 4 stars!
View More Like This Naot Footwear - Levanto
Naot Footwear Levanto $219.95 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 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 Rockport - Ledge Hill 2 Chukka Boot
Rockport Ledge Hill 2 Chukka Boot $149.95 $139.95 Rated: 4 stars!
View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!
View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!

View More Like This Stacy Adams - Madison II - 65
Stacy Adams Madison II - 65 $180.00 Rated: 4 stars!
View More Like This SoftWalk - Ramsey
SoftWalk Ramsey $124.95 Rated: 4 stars!
View More Like This SoftWalk - Ramsey
SoftWalk Ramsey $124.95 Rated: 4 stars!
View More Like This SoftWalk - Ramsey
SoftWalk Ramsey $124.95 Rated: 4 stars!

View More Like This Frye - Oliver Chukka
Frye Oliver Chukka $278.00 $194.60 Rated: 4 stars!
View More Like This Wolverine - Hensel
Wolverine Hensel $195.00 Rated: 4 stars!
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 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 Stacy Adams - Burgess Cap Toe Chukka Boot
Stacy Adams Burgess Cap Toe Chukka Boot $105.00 Rated: 4 stars!
View More Like This Nunn Bush - Hawley Plain Toe Chukka
Nunn Bush Hawley Plain Toe Chukka $95.00 $76.00 Rated: 4 stars!
View More Like This Nunn Bush - Hawley Plain Toe Chukka
Nunn Bush Hawley Plain Toe Chukka $95.00 $76.00 Rated: 4 stars!
View More Like This Calvin Klein - Jae
Calvin Klein Jae $140.00 $97.99 Rated: 4 stars!

View More Like This Stacy Adams - Madison II - 65
Stacy Adams Madison II - 65 $180.00 Rated: 4 stars!
View More Like This Stacy Adams - Madison II - 65
Stacy Adams Madison II - 65 $180.00 Rated: 4 stars!
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 Nunn Bush - Nichols Wingtip Chukka Boot
Nunn Bush Nichols Wingtip Chukka Boot $90.00 $72.00 Rated: 3 stars!

View More Like This Deer Stags - Mean
Deer Stags Mean $60.00 Rated: 3 stars!
View More Like This Deer Stags - Mean
Deer Stags Mean $70.00 Rated: 3 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 Hush Puppies - Waterproof Benson Rigby ICE+
Hush Puppies Waterproof Benson Rigby ICE+ $180.00 Rated: 2 stars!