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Boots on Sale $50 & Under

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Leather Chukka Boots

32 items found

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Koolaburra by UGG - Advay. Color Black. On sale for $62.29. MSRP $84.99. 27% off. 3.7 out of 5 stars

Koolaburra by UGG Advay

Koolaburra by UGG Advay

Brand Name: Koolaburra by UGG
Product Name: Advay
Gender: Women's
Color: Black
Price: $62.29MSRP: $84.99

Steve Madden - Palta. Color Sand. Low Stock. On sale for $39.60. MSRP $130.00. 70% off.

Low Stock

Steve Madden Palta

Steve Madden Palta

Brand Name: Steve Madden
Product Name: Palta
Gender: Men's
Color: Sand
Price: $39.60MSRP: $130

Comfortiva - Holland. Color Olive. Low Stock. On sale for $56.23. MSRP $129.95. 57% off. 3.8 out of 5 stars

Low Stock

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Olive
Price: $56.23MSRP: $129.95

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Brown CH. Low Stock. On sale for $34.50. MSRP $115.00. 70% off. 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: Brown CH
Price: $34.50MSRP: $115

Sperry - A/O Plushwave Lug Chukka. Color Black 2. Low Stock. On sale for $58.01. MSRP $140.00. 59% off. 4.1 out of 5 stars

Low Stock

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: $58.01MSRP: $140

Hey Dude - Reyes Boots Wool. Color Light Grey. Low Stock. On sale for $22.74. MSRP $89.99. 75% off. 4.2 out of 5 stars

Low Stock

Hey Dude Reyes Boots Wool

Hey Dude Reyes Boots Wool

Brand Name: Hey Dude
Product Name: Reyes Boots Wool
Gender: Women's
Color: Light Grey
Price: $22.74MSRP: $89.99

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. Low Stock. On sale for $40.25. MSRP $115.00. 65% off. 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: Black Tumbled
Price: $40.25MSRP: $115

Cole Haan - Grand Remix Chukka. Color Morel Nubuck/Ivory. On sale for $119.00. MSRP $140.00. 15% off. 4.0 out of 5 stars

Cole Haan Grand Remix Chukka

Cole Haan Grand Remix Chukka

Brand Name: Cole Haan
Product Name: Grand Remix Chukka
Gender: Men's
Color: Morel Nubuck/Ivory
Price: $119MSRP: $140

Dr. Scholl's - Manchester. Color Grey Faux Leather. Low Stock. On sale for $54.84. MSRP $120.00. 54% off. 3.0 out of 5 stars

Low Stock

Dr. Scholl's Manchester

Dr. Scholl's Manchester

Brand Name: Dr. Scholl's
Product Name: Manchester
Gender: Men's
Color: Grey Faux Leather
Price: $54.84MSRP: $120

Tommy Hilfiger - Natash. Color Black. Low Stock. On sale for $54.50. MSRP $109.00. 50% off.

Low Stock

Tommy Hilfiger Natash

Tommy Hilfiger Natash

Brand Name: Tommy Hilfiger
Product Name: Natash
Gender: Men's
Color: Black
Price: $54.50MSRP: $109

Koolaburra by UGG - Advay. Color Dune. On sale for $69.97. MSRP $84.99. 18% off. 3.7 out of 5 stars

Koolaburra by UGG Advay

Koolaburra by UGG Advay

Brand Name: Koolaburra by UGG
Product Name: Advay
Gender: Women's
Color: Dune
Price: $69.97MSRP: $84.99

Clarks - Shepton. Color Sand Suede. On sale for $82.50. MSRP $110.00. 25% off. 1.7 out of 5 stars

Clarks Shepton

Clarks Shepton

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Sand Suede
Price: $82.50MSRP: $110

Dolce Vita - Ronnie. Color Camel Suede. Low Stock. On sale for $43.99. MSRP $220.00. 80% off. 3.5 out of 5 stars

Low Stock

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Camel Suede
Price: $43.99MSRP: $220

Gordon Rush - Austin. Color Espresso. Low Stock. $145.75. 3.0 out of 5 stars

Low Stock

Gordon Rush Austin

Gordon Rush Austin

Brand Name: Gordon Rush
Product Name: Austin
Gender: Men's
Color: Espresso
Price: $145.75

Propet - Findley. Color Tan. Low Stock. On sale for $91.96. MSRP $134.99. 32% off. 3.6 out of 5 stars

Low Stock

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Tan
Price: $91.96MSRP: $134.99

Cole Haan - Berkshire Lug Chukka Boots. Color Pavement Nubuck/Demitasse Water Resistant. Low Stock. $220.00. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Lug Chukka Boots

Cole Haan Berkshire Lug Chukka Boots

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boots
Gender: Men's
Color: Pavement Nubuck/Demitasse Water Resistant
Price: $220

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $88.00. MSRP $125.00. 30% off. 4.6 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: $88MSRP: $125

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $92.54. MSRP $115.00. 20% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Madison Men's Chukka

Dr. Scholl's Madison Men's Chukka

Brand Name: Dr. Scholl's
Product Name: Madison Men's Chukka
Gender: Men's
Color: Mocha Taupe Textured Nubuck
Price: $92.54MSRP: $115

Nunn Bush - Otto Plain Toe Chukka Boots. Color Gray. Low Stock. On sale for $79.95. MSRP $120.00. 33% off. 4.1 out of 5 stars

Low Stock

Nunn Bush Otto Plain Toe Chukka Boots

Nunn Bush Otto Plain Toe Chukka Boots

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boots
Gender: Men's
Color: Gray
Price: $79.95MSRP: $120

Stuart Weitzman - Soluxe Hudson Chukka. Color Doe. On sale for $585.00. MSRP $650.00. 10% off.

Stuart Weitzman Soluxe Hudson Chukka

Stuart Weitzman Soluxe Hudson Chukka

Brand Name: Stuart Weitzman
Product Name: Soluxe Hudson Chukka
Gender: Women's
Color: Doe
Price: $585MSRP: $650

Stuart Weitzman - Soluxe Hudson Chukka. Color Black 1. On sale for $625.50. MSRP $695.00. 10% off.

Stuart Weitzman Soluxe Hudson Chukka

Stuart Weitzman Soluxe Hudson Chukka

Brand Name: Stuart Weitzman
Product Name: Soluxe Hudson Chukka
Gender: Women's
Color: Black 1
Price: $625.50MSRP: $695

Cole Haan - Berkshire Lug Chukka Boots. Color British Tan/C. On sale for $118.95. MSRP $260.00. 54% off. 4.5 out of 5 stars

Cole Haan Berkshire Lug Chukka Boots

Cole Haan Berkshire Lug Chukka Boots

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boots
Gender: Men's
Color: British Tan/C
Price: $118.95MSRP: $260

Cole Haan - Berkshire Lug Chukka Boots. Color Lava Suede/Dark. Low Stock. On sale for $210.81. MSRP $250.00. 16% off. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Lug Chukka Boots

Cole Haan Berkshire Lug Chukka Boots

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boots
Gender: Men's
Color: Lava Suede/Dark
Price: $210.81MSRP: $250

Moral Code - Faye Chukka Boot. Color Cognac. Low Stock. On sale for $101.75. MSRP $185.00. 45% off.

Low Stock

Moral Code Faye Chukka Boot

Moral Code Faye Chukka Boot

Brand Name: Moral Code
Product Name: Faye Chukka Boot
Gender: Women's
Color: Cognac
Price: $101.75MSRP: $185

ECCO - Grainer Chukka Boot. Color Camel. On sale for $142.86. MSRP $190.00. 25% off. 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: $142.86MSRP: $190

Steve Madden - Hestonn - Extended Sizes. Color Tan Leather. On sale for $76.07. MSRP $109.99. 31% off. 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: $76.07MSRP: $109.99

Steve Madden - Harken - Extended Sizes. Color Black. Low Stock. On sale for $80.29. MSRP $109.99. 27% off. 4.1 out of 5 stars

Low Stock

Steve Madden Harken - Extended Sizes

Steve Madden Harken - Extended Sizes

Brand Name: Steve Madden
Product Name: Harken - Extended Sizes
Gender: Men's
Color: Black
Price: $80.29MSRP: $109.99

Dolce Vita - Ronnie. Color Black Leather. Low Stock. On sale for $44.00. MSRP $220.00. 80% off. 3.5 out of 5 stars

Low Stock

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Black Leather
Price: $44MSRP: $220

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $213.75. MSRP $285.00. 25% off.

Low Stock

Johnston & Murphy Bolivar Plain Toe Boots

Johnston & Murphy Bolivar Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Bolivar Plain Toe Boots
Gender: Men's
Color: Snuff Italian Suede
Price: $213.75MSRP: $285

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. On sale for $170.00. MSRP $200.00. 15% off. 2.7 out of 5 stars

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Woodbury/Dark Roast
Price: $170MSRP: $200

Comfortiva - Holland. Color Light Grey. On sale for $69.37. MSRP $129.95. 47% off. 3.8 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Light Grey
Price: $69.37MSRP: $129.95

Comfortiva - Holland. Color Black. On sale for $69.13. MSRP $129.95. 47% off. 3.8 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Black
Price: $69.13MSRP: $129.95