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Boots on Sale $50 or Less!

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Men Chukka Boots

52 items found

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Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $99.00. MSRP $125.00.. 4.8 out of 5 stars

Stacy Adams Maxwell Plain Toe Demi Boot

Stacy Adams Maxwell Plain Toe Demi Boot

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $99.00MSRP: $125.00

Steve Madden - Yvor. Color Grey Suede. Low Stock. On sale for $105.00. MSRP $140.00.. 2.0 out of 5 stars

Low Stock

Steve Madden Yvor

Steve Madden Yvor

Brand Name: Steve Madden
Product Name: Yvor
Gender: Men's
Color: Grey Suede
Price: $105.00MSRP: $140.00

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $97.75. MSRP $115.00.. 4.3 out of 5 stars

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $97.75MSRP: $115.00

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $91.00. MSRP $115.00.. 4.3 out of 5 stars

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $91.00MSRP: $115.00

Sperry - A/O Plushwave Lug Chukka. Color Black 2. On sale for $95.94. MSRP $140.00.. 4.1 out of 5 stars

Sperry A/O Plushwave Lug Chukka

Sperry A/O Plushwave Lug Chukka

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Gender: Men's
Color: Black 2
Price: $95.94MSRP: $140.00

Cole Haan - Hawthorne Chukka Boot. Color Dark Chocolate. On sale for $115.86. MSRP $140.00.. 4.5 out of 5 stars

Cole Haan Hawthorne Chukka Boot

Cole Haan Hawthorne Chukka Boot

Brand Name: Cole Haan
Product Name: Hawthorne Chukka Boot
Gender: Men's
Color: Dark Chocolate
Price: $115.86MSRP: $140.00

Propet - Findley. Color Black. On sale for $95.00. MSRP $134.95.. 3.6 out of 5 stars

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Black
Price: $95.00MSRP: $134.95

Johnston & Murphy - Braydon Chukka. Color Charcoal Waxed Suede. On sale for $93.61. MSRP $149.00..

Johnston & Murphy Braydon Chukka

Johnston & Murphy Braydon Chukka

Brand Name: Johnston & Murphy
Product Name: Braydon Chukka
Gender: Men's
Color: Charcoal Waxed Suede
Price: $93.61MSRP: $149.00

Cole Haan - Original Grand Chukka. Color Black Leather/Black. Low Stock. On sale for $162.00. MSRP $180.00.. 4.6 out of 5 stars

Low Stock

Cole Haan Original Grand Chukka

Cole Haan Original Grand Chukka

Brand Name: Cole Haan
Product Name: Original Grand Chukka
Gender: Men's
Color: Black Leather/Black
Price: $162.00MSRP: $180.00

Cole Haan - Original Grand Chukka. Color Woodbury Leather/Ivory. Low Stock. On sale for $162.00. MSRP $180.00.. 4.6 out of 5 stars

Low Stock

Cole Haan Original Grand Chukka

Cole Haan Original Grand Chukka

Brand Name: Cole Haan
Product Name: Original Grand Chukka
Gender: Men's
Color: Woodbury Leather/Ivory
Price: $162.00MSRP: $180.00

Steve Madden - Hestonn - Extended Sizes. Color Tan Leather. On sale for $90.00. MSRP $95.00.. 3.9 out of 5 stars

Steve Madden Hestonn - Extended Sizes

Steve Madden Hestonn - Extended Sizes

Brand Name: Steve Madden
Product Name: Hestonn - Extended Sizes
Gender: Men's
Color: Tan Leather
Price: $90.00MSRP: $95.00

Cole Haan - Berkshire Lug Chukka Boot. Color Lava Suede/Dark. On sale for $187.50. MSRP $250.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Lava Suede/Dark
Price: $187.50MSRP: $250.00

Ben Sherman - Dirk Chukka. Color Tan PU. Low Stock. On sale for $90.00. MSRP $120.00..

Low Stock

Ben Sherman Dirk Chukka

Ben Sherman Dirk Chukka

Brand Name: Ben Sherman
Product Name: Dirk Chukka
Gender: Men's
Color: Tan PU
Price: $90.00MSRP: $120.00

ECCO - Grainer Chukka Boot. Color Camel. On sale for $150.29. MSRP $190.00.. 2.5 out of 5 stars

ECCO Grainer Chukka Boot

ECCO Grainer Chukka Boot

Brand Name: ECCO
Product Name: Grainer Chukka Boot
Gender: Men's
Color: Camel
Price: $150.29MSRP: $190.00

Cole Haan - Berkshire Lug Chukka Boot. Color Bloodstone/Dark Natural Water Resistant. On sale for $144.00. MSRP $240.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Bloodstone/Dark Natural Water Resistant
Price: $144.00MSRP: $240.00

ECCO - London Plain Toe Chukka Boots. Color Cognac. On sale for $149.99. MSRP $225.00..

ECCO London Plain Toe Chukka Boots

ECCO London Plain Toe Chukka Boots

Brand Name: ECCO
Product Name: London Plain Toe Chukka Boots
Gender: Men's
Color: Cognac
Price: $149.99MSRP: $225.00

Steve Madden - Graper Chukka. Color Black. Low Stock. On sale for $45.71. MSRP $74.95.. 5.0 out of 5 stars

Low Stock

Steve Madden Graper Chukka

Steve Madden Graper Chukka

Brand Name: Steve Madden
Product Name: Graper Chukka
Gender: Men's
Color: Black
Price: $45.71MSRP: $74.95

Thomas & Vine - Cutler Embossed Chukka Boot. Color Black. Low Stock. On sale for $72.49. MSRP $124.99..

Low Stock

Thomas & Vine Cutler Embossed Chukka Boot

Thomas & Vine Cutler Embossed Chukka Boot

Brand Name: Thomas & Vine
Product Name: Cutler Embossed Chukka Boot
Gender: Men's
Color: Black
Price: $72.49MSRP: $124.99

Tommy Hilfiger - Gibby. Color Black. Low Stock. On sale for $71.95. MSRP $79.95.. 4.5 out of 5 stars

Low Stock

Tommy Hilfiger Gibby

Tommy Hilfiger Gibby

Brand Name: Tommy Hilfiger
Product Name: Gibby
Gender: Men's
Color: Black
Price: $71.95MSRP: $79.95

Johnston & Murphy - Upton Chukka. Color Navy Nubuck. Low Stock. On sale for $105.43. MSRP $169.00.. 4.4 out of 5 stars

Low Stock

Johnston & Murphy Upton Chukka

Johnston & Murphy Upton Chukka

Brand Name: Johnston & Murphy
Product Name: Upton Chukka
Gender: Men's
Color: Navy Nubuck
Price: $105.43MSRP: $169.00

Clarks - Corston Wally Waterproof. Color Black Leather Waterproof. Low Stock. On sale for $88.00. MSRP $170.00.. 3.0 out of 5 stars

Low Stock

Clarks Corston Wally Waterproof

Clarks Corston Wally Waterproof

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Gender: Men's
Color: Black Leather Waterproof
Price: $88.00MSRP: $170.00

Clarks - Corston Wally Waterproof. Color Olive Leather Waterproof. Low Stock. On sale for $76.47. MSRP $170.00.. 3.0 out of 5 stars

Low Stock

Clarks Corston Wally Waterproof

Clarks Corston Wally Waterproof

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Gender: Men's
Color: Olive Leather Waterproof
Price: $76.47MSRP: $170.00

Roper - Gum Sticker. Color Tan 1. Low Stock. On sale for $79.76. MSRP $139.99.. 5.0 out of 5 stars

Low Stock

Roper Gum Sticker

Roper Gum Sticker

Brand Name: Roper
Product Name: Gum Sticker
Gender: Men's
Color: Tan 1
Price: $79.76MSRP: $139.99

Clarks - Bruno Top. Color Light Brown Leather. Low Stock. On sale for $97.96. MSRP $140.00.. 3.0 out of 5 stars

Low Stock

Clarks Bruno Top

Clarks Bruno Top

Brand Name: Clarks
Product Name: Bruno Top
Gender: Men's
Color: Light Brown Leather
Price: $97.96MSRP: $140.00

Stacy Adams - Tilden Chukka Boot. Color Cocoa. Low Stock. On sale for $49.17. MSRP $119.95.. 3.8 out of 5 stars

Low Stock

Stacy Adams Tilden Chukka Boot

Stacy Adams Tilden Chukka Boot

Brand Name: Stacy Adams
Product Name: Tilden Chukka Boot
Gender: Men's
Color: Cocoa
Price: $49.17MSRP: $119.95

Stacy Adams - Hartley Chukka Boot. Color Black/Gray. Low Stock. On sale for $71.78. MSRP $104.95.. 4.6 out of 5 stars

Low Stock

Stacy Adams Hartley Chukka Boot

Stacy Adams Hartley Chukka Boot

Brand Name: Stacy Adams
Product Name: Hartley Chukka Boot
Gender: Men's
Color: Black/Gray
Price: $71.78MSRP: $104.95

PIKOLINOS - Tolosa M7N-8177C1. Color Olmo. Low Stock. On sale for $138.60. MSRP $220.00..

Low Stock

PIKOLINOS Tolosa M7N-8177C1

PIKOLINOS Tolosa M7N-8177C1

Brand Name: PIKOLINOS
Product Name: Tolosa M7N-8177C1
Gender: Men's
Color: Olmo
Price: $138.60MSRP: $220.00

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Tan CH. Low Stock. On sale for $85.10. MSRP $115.00.. 4.3 out of 5 stars

Low Stock

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Tan CH
Price: $85.10MSRP: $115.00

johnnie-O - Chill Chukka 2.0. Color Gray. Low Stock. On sale for $64.35. MSRP $198.00..

Low Stock

johnnie-O Chill Chukka 2.0

johnnie-O Chill Chukka 2.0

Brand Name: johnnie-O
Product Name: Chill Chukka 2.0
Gender: Men's
Color: Gray
Price: $64.35MSRP: $198.00

Clarks - Nature 5 Mid. Color Beeswax Combi. Low Stock. On sale for $98.96. MSRP $150.00.. 2.0 out of 5 stars

Low Stock

Clarks Nature 5 Mid

Clarks Nature 5 Mid

Brand Name: Clarks
Product Name: Nature 5 Mid
Gender: Men's
Color: Beeswax Combi
Price: $98.96MSRP: $150.00

Thomas & Vine - Deacon Chukka Boot. Color Grey. Low Stock. On sale for $19.99. MSRP $99.99.. 3.9 out of 5 stars

Low Stock

Thomas & Vine Deacon Chukka Boot

Thomas & Vine Deacon Chukka Boot

Brand Name: Thomas & Vine
Product Name: Deacon Chukka Boot
Gender: Men's
Color: Grey
Price: $19.99MSRP: $99.99

Eastland 1955 Edition - Jack. Color Oak. Low Stock. On sale for $117.60. MSRP $140.00.. 4.2 out of 5 stars

Low Stock

Eastland 1955 Edition Jack

Eastland 1955 Edition Jack

Brand Name: Eastland 1955 Edition
Product Name: Jack
Gender: Men's
Color: Oak
Price: $117.60MSRP: $140.00

Ted Baker - Appell. Color Stone. Low Stock. On sale for $101.40. MSRP $195.00..

Low Stock

Ted Baker Appell

Ted Baker Appell

Brand Name: Ted Baker
Product Name: Appell
Gender: Men's
Color: Stone
Price: $101.40MSRP: $195.00

Ted Baker - Appell. Color Burnt Red. Low Stock. On sale for $74.10. MSRP $195.00..

Low Stock

Ted Baker Appell

Ted Baker Appell

Brand Name: Ted Baker
Product Name: Appell
Gender: Men's
Color: Burnt Red
Price: $74.10MSRP: $195.00

Propet - Findley. Color Tan. Low Stock. On sale for $95.00. MSRP $134.95.. 3.6 out of 5 stars

Low Stock

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Tan
Price: $95.00MSRP: $134.95

Roper - Performance 2-Eyelet Ankle Boot. Color Brown Ostrich. Low Stock. On sale for $63.49. MSRP $126.99.. 4.6 out of 5 stars

Low Stock

Roper Performance 2-Eyelet Ankle Boot

Roper Performance 2-Eyelet Ankle Boot

Brand Name: Roper
Product Name: Performance 2-Eyelet Ankle Boot
Gender: Men's
Color: Brown Ostrich
Price: $63.49MSRP: $126.99

ECCO - Turn GORE-TEX® Chukka Tie. Color Black. Low Stock. On sale for $200.71. MSRP $250.00.. 4.3 out of 5 stars

Low Stock

ECCO Turn GORE-TEX® Chukka Tie

ECCO Turn GORE-TEX® Chukka Tie

Brand Name: ECCO
Product Name: Turn GORE-TEX® Chukka Tie
Gender: Men's
Color: Black
Price: $200.71MSRP: $250.00

Baretraps - Higgins Lace-Up Boot. Color Grey Suede. Low Stock. On sale for $80.50. MSRP $115.00..

Low Stock

Baretraps Higgins Lace-Up Boot

Brand Name: Baretraps
Product Name: Higgins Lace-Up Boot
Gender: Men's
Color: Grey Suede
Price: $80.50MSRP: $115.00

Fred Perry - Hawley Suede. Color Black. Low Stock. On sale for $131.25. MSRP $175.00.. 4.0 out of 5 stars

Low Stock

Fred Perry Hawley Suede

Fred Perry Hawley Suede

Brand Name: Fred Perry
Product Name: Hawley Suede
Gender: Men's
Color: Black
Price: $131.25MSRP: $175.00

Blake McKay - Alder. Color Tan. Low Stock. On sale for $80.85. MSRP $165.00..

Low Stock

Blake McKay Alder

Blake McKay Alder

Brand Name: Blake McKay
Product Name: Alder
Gender: Men's
Color: Tan
Price: $80.85MSRP: $165.00

Blake McKay - Alder. Color Black. Low Stock. On sale for $74.25. MSRP $165.00..

Low Stock

Blake McKay Alder

Blake McKay Alder

Brand Name: Blake McKay
Product Name: Alder
Gender: Men's
Color: Black
Price: $74.25MSRP: $165.00

Florsheim - Uptown Plain Toe Chukka Boot. Color Brown Crazy Horse Pull Up. Low Stock. On sale for $59.80. MSRP $130.00.. 4.4 out of 5 stars

Low Stock

Florsheim Uptown Plain Toe Chukka Boot

Florsheim Uptown Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Uptown Plain Toe Chukka Boot
Gender: Men's
Color: Brown Crazy Horse Pull Up
Price: $59.80MSRP: $130.00

Chaco - Paonia Desert Boot. Color Teak. Low Stock. $139.95.

Low Stock

Chaco Paonia Desert Boot

Chaco Paonia Desert Boot

Brand Name: Chaco
Product Name: Paonia Desert Boot
Gender: Men's
Color: Teak
Price: $139.95

Clarks - Malwood Top. Color Cola Suede. Low Stock. On sale for $86.86. MSRP $110.00.. 3.0 out of 5 stars

Low Stock

Clarks Malwood Top

Clarks Malwood Top

Brand Name: Clarks
Product Name: Malwood Top
Gender: Men's
Color: Cola Suede
Price: $86.86MSRP: $110.00

SeaVees - Maslon Desert Boot Carr. Color Black. Low Stock. On sale for $52.80. MSRP $120.00.. 5.0 out of 5 stars

Low Stock

SeaVees Maslon Desert Boot Carr

SeaVees Maslon Desert Boot Carr

Brand Name: SeaVees
Product Name: Maslon Desert Boot Carr
Gender: Men's
Color: Black
Price: $52.80MSRP: $120.00

SeaVees - Maslon Desert Boot Carr. Color Coffee. Low Stock. On sale for $70.80. MSRP $120.00.. 5.0 out of 5 stars

Low Stock

SeaVees Maslon Desert Boot Carr

SeaVees Maslon Desert Boot Carr

Brand Name: SeaVees
Product Name: Maslon Desert Boot Carr
Gender: Men's
Color: Coffee
Price: $70.80MSRP: $120.00

SOREL - Madson™ II Chukka Waterproof. Color Cashew/Tobacco. Low Stock. On sale for $114.00. MSRP $190.00.. 4.5 out of 5 stars

Low Stock

SOREL Madson™ II Chukka Waterproof

SOREL Madson™ II Chukka Waterproof

Brand Name: SOREL
Product Name: Madson™ II Chukka Waterproof
Gender: Men's
Color: Cashew/Tobacco
Price: $114.00MSRP: $190.00

SOREL - Madson™ II Chukka Waterproof. Color Tawny Buff. Low Stock. On sale for $114.00. MSRP $190.00.. 4.5 out of 5 stars

Low Stock

SOREL Madson™ II Chukka Waterproof

SOREL Madson™ II Chukka Waterproof

Brand Name: SOREL
Product Name: Madson™ II Chukka Waterproof
Gender: Men's
Color: Tawny Buff
Price: $114.00MSRP: $190.00

SeaVees - Maslon Desert Boot. Color Natural. Low Stock. On sale for $72.90. MSRP $120.00..

Low Stock

SeaVees Maslon Desert Boot

SeaVees Maslon Desert Boot

Brand Name: SeaVees
Product Name: Maslon Desert Boot
Gender: Men's
Color: Natural
Price: $72.90MSRP: $120.00

Vince Camuto - Tadesse Chukka Boot. Color Mocha. Low Stock. On sale for $134.25. MSRP $179.00..

Low Stock

Vince Camuto Tadesse Chukka Boot

Vince Camuto Tadesse Chukka Boot

Brand Name: Vince Camuto
Product Name: Tadesse Chukka Boot
Gender: Men's
Color: Mocha
Price: $134.25MSRP: $179.00

Rockport - Berenger Plain Toe Chukka. Color Tan. Low Stock. On sale for $99.57. MSRP $119.95.. 3.5 out of 5 stars

Low Stock

Rockport Berenger Plain Toe Chukka

Rockport Berenger Plain Toe Chukka

Brand Name: Rockport
Product Name: Berenger Plain Toe Chukka
Gender: Men's
Color: Tan
Price: $99.57MSRP: $119.95

Thomas & Vine - Cutler Embossed Chukka Boot. Color Brown. Low Stock. On sale for $63.74. MSRP $124.99..

Low Stock

Thomas & Vine Cutler Embossed Chukka Boot

Thomas & Vine Cutler Embossed Chukka Boot

Brand Name: Thomas & Vine
Product Name: Cutler Embossed Chukka Boot
Gender: Men's
Color: Brown
Price: $63.74MSRP: $124.99