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Boots on Sale $50 & Under

Shop Boots Deals

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massimo matteo chukka classic boots

15 items found

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Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. On sale for $149.95. MSRP $200.00. 25% 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: $149.95MSRP: $200

The Original Muck Boot Company - Edgewater Classic. Color Black. Low Stock. On sale for $100.59. MSRP $115.00. 13% off. 3.0 out of 5 stars

Low Stock

The Original Muck Boot Company Edgewater Classic

The Original Muck Boot Company Edgewater Classic

Brand Name: The Original Muck Boot Company
Product Name: Edgewater Classic
Gender: Men's
Color: Black
Price: $100.59MSRP: $115

Sperry - Cold Bay Chukka Realtree. Color Olive. On sale for $109.51. MSRP $120.00. 9% off.

Sperry Cold Bay Chukka Realtree

Sperry Cold Bay Chukka Realtree

Brand Name: Sperry
Product Name: Cold Bay Chukka Realtree
Gender: Men's
Color: Olive
Price: $109.51MSRP: $120

SeaVees - Maslon Desert Boot. Color Natural. Low Stock. On sale for $24.00. MSRP $120.00. 80% off.

Low Stock

SeaVees Maslon Desert Boot

SeaVees Maslon Desert Boot

Brand Name: SeaVees
Product Name: Maslon Desert Boot
Gender: Men's
Color: Natural
Price: $24MSRP: $120

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

Eastland 1955 Edition - Hugo. Color Brown. Low Stock. On sale for $70.00. MSRP $100.00. 30% off.

Low Stock

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Brown
Price: $70MSRP: $100

UGG - Neumel Crafted Regenerate. Color Chestnut. On sale for $134.99. MSRP $210.00. 36% off. 4.0 out of 5 stars

UGG Neumel Crafted Regenerate

UGG Neumel Crafted Regenerate

Brand Name: UGG
Product Name: Neumel Crafted Regenerate
Gender: Unisex
Color: Chestnut
Price: $134.99MSRP: $210

Kenneth Cole - Vesto. Color Black. $118.95.

Kenneth Cole Vesto

Kenneth Cole Vesto

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Black
Price: $118.95

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

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

Clarks - Relaxlite Moc. Color Black Suede. Low Stock. On sale for $99.00. MSRP $110.00. 10% off.

Low Stock

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Black Suede
Price: $99MSRP: $110

Dockers - Norton. Color Taupe. Low Stock. On sale for $69.39. MSRP $85.00. 18% off. 2.6 out of 5 stars

Low Stock

Dockers Norton

Dockers Norton

Brand Name: Dockers
Product Name: Norton
Gender: Men's
Color: Taupe
Price: $69.39MSRP: $85

Clarks - Relaxlite Moc. Color Cola Suede. On sale for $84.00. MSRP $110.00. 24% off.

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Cola Suede
Price: $84MSRP: $110

Dockers - Norton. Color Dark Brown. Low Stock. On sale for $59.50. MSRP $85.00. 30% off. 2.6 out of 5 stars

Low Stock

Dockers Norton

Dockers Norton

Brand Name: Dockers
Product Name: Norton
Gender: Men's
Color: Dark Brown
Price: $59.50MSRP: $85

Clarks - Shepton. Color Sand Suede. On sale for $71.50. MSRP $110.00. 35% off. 1.7 out of 5 stars

Clarks Shepton

Clarks Shepton

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Sand Suede
Price: $71.50MSRP: $110