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Boots on Sale $50 & Under

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gentle souls by kenneth cole mateo driver penny

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Cole Haan - Grand Laser Penny Driver. Color Cherry Mahogany. On sale for $107.47. MSRP $140.00. 23% off. 3.9 out of 5 stars

Cole Haan Grand Laser Penny Driver

Cole Haan Grand Laser Penny Driver

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Cherry Mahogany
Price: $107.47MSRP: $140.00

Kenneth Cole Reaction - White Evening Jacket. Color White. Low Stock. On sale for $132.75. MSRP $295.00. 55% off.

Low Stock

Kenneth Cole Reaction White Evening Jacket

Kenneth Cole Reaction White Evening Jacket

Brand Name: Kenneth Cole Reaction
Product Name: White Evening Jacket
Gender: Men's
Color: White
Price: $132.75MSRP: $295.00

Johnston & Murphy - Jameson Penny. Color Brown. Low Stock. On sale for $185.25. MSRP $285.00. 35% off. 4.1 out of 5 stars

Low Stock

Johnston & Murphy Jameson Penny

Johnston & Murphy Jameson Penny

Brand Name: Johnston & Murphy
Product Name: Jameson Penny
Gender: Men's
Color: Brown
Price: $185.25MSRP: $285.00

Carlos by Carlos Santana - Ritchie Driver Loafer. Color Camel Calf Nubuck. Low Stock. On sale for $53.37. MSRP $88.95. 40% off. 3.9 out of 5 stars

Low Stock

Carlos by Carlos Santana Ritchie Driver Loafer

Carlos by Carlos Santana Ritchie Driver Loafer

Brand Name: Carlos by Carlos Santana
Product Name: Ritchie Driver Loafer
Gender: Men's
Color: Camel Calf Nubuck
Price: $53.37MSRP: $88.95

Cole Haan - Wyatt Bit Drivers. Color Big Dipper Nubuck/Sea Stone. Low Stock. On sale for $117.00. MSRP $130.00. 10% off. 3.8 out of 5 stars

Low Stock

Cole Haan Wyatt Bit Drivers

Cole Haan Wyatt Bit Drivers

Brand Name: Cole Haan
Product Name: Wyatt Bit Drivers
Gender: Men's
Color: Big Dipper Nubuck/Sea Stone
Price: $117.00MSRP: $130.00

Cole Haan - Grand Laser Bit Driver. Color Big Dipper Suede/Gum. Low Stock. On sale for $122.39. MSRP $150.00. 18% off. 4.0 out of 5 stars

Low Stock

Cole Haan Grand Laser Bit Driver

Cole Haan Grand Laser Bit Driver

Brand Name: Cole Haan
Product Name: Grand Laser Bit Driver
Gender: Men's
Color: Big Dipper Suede/Gum
Price: $122.39MSRP: $150.00

To Boot New York - Mitchum. Color Sand. Low Stock. On sale for $178.75. MSRP $325.00. 45% off. 4.3 out of 5 stars

Low Stock

To Boot New York Mitchum

To Boot New York Mitchum

Brand Name: To Boot New York
Product Name: Mitchum
Gender: Men's
Color: Sand
Price: $178.75MSRP: $325.00

Massimo Matteo - Pitstop Penny Driver. Color Black. Low Stock. On sale for $41.30. MSRP $59.00. 30% off. 4.3 out of 5 stars

Low Stock

Massimo Matteo Pitstop Penny Driver

Massimo Matteo Pitstop Penny Driver

Brand Name: Massimo Matteo
Product Name: Pitstop Penny Driver
Gender: Men's
Color: Black
Price: $41.30MSRP: $59.00

Cole Haan - Pinch Prep Penny Loafer. Color Birchbeige Suede/Dark Chocolate. On sale for $122.82. MSRP $130.00. 6% off. 3.9 out of 5 stars

Cole Haan Pinch Prep Penny Loafer

Cole Haan Pinch Prep Penny Loafer

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Birchbeige Suede/Dark Chocolate
Price: $122.82MSRP: $130.00

Cole Haan - American Classics Penny Loafer. Color Hickory/Birchbeige. Low Stock. On sale for $142.20. MSRP $158.00. 10% off. 4.2 out of 5 stars

Low Stock

Cole Haan American Classics Penny Loafer

Cole Haan American Classics Penny Loafer

Brand Name: Cole Haan
Product Name: American Classics Penny Loafer
Gender: Men's
Color: Hickory/Birchbeige
Price: $142.20MSRP: $158.00

Cole Haan - Nantucket Penny Txt. Color Light Sesame/Biscuit/Ivory. On sale for $76.50. MSRP $85.00. 10% off.

Cole Haan Nantucket Penny Txt

Cole Haan Nantucket Penny Txt

Brand Name: Cole Haan
Product Name: Nantucket Penny Txt
Gender: Men's
Color: Light Sesame/Biscuit/Ivory
Price: $76.50MSRP: $85.00

Cole Haan - Pinch Prep Penny Loafer. Color Dark Chocolate BOX Brush Off/Black. On sale for $119.97. MSRP $140.00. 14% off. 3.9 out of 5 stars

Cole Haan Pinch Prep Penny Loafer

Cole Haan Pinch Prep Penny Loafer

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Dark Chocolate BOX Brush Off/Black
Price: $119.97MSRP: $140.00

Cole Haan - Pinch Weekender Penny Textured. Color Dark Chocolate Pebble/Ivory. On sale for $81.33. MSRP $100.00. 19% off. 4.7 out of 5 stars

Cole Haan Pinch Weekender Penny Textured

Cole Haan Pinch Weekender Penny Textured

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny Textured
Gender: Men's
Color: Dark Chocolate Pebble/Ivory
Price: $81.33MSRP: $100.00

Cole Haan - Nantucket Penny. Color Black Canvas/Black/Ivory. On sale for $76.27. MSRP $80.00. 5% off. 3.0 out of 5 stars

Cole Haan Nantucket Penny

Cole Haan Nantucket Penny

Brand Name: Cole Haan
Product Name: Nantucket Penny
Gender: Men's
Color: Black Canvas/Black/Ivory
Price: $76.27MSRP: $80.00

Cole Haan - Pinch Weekender Penny. Color Black/Angora. On sale for $108.81. MSRP $120.00. 9% off. 4.2 out of 5 stars

Cole Haan Pinch Weekender Penny

Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: Black/Angora
Price: $108.81MSRP: $120.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Navy Blazer Stamped/Lava Smoke/Sea Stone. On sale for $171.00. MSRP $190.00. 10% off. 5.0 out of 5 stars

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Navy Blazer Stamped/Lava Smoke/Sea Stone
Price: $171.00MSRP: $190.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Woodbury Stamped/Ancient Scroll. Low Stock. On sale for $171.00. MSRP $190.00. 10% off. 5.0 out of 5 stars

Low Stock

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Woodbury Stamped/Ancient Scroll
Price: $171.00MSRP: $190.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Black Stamped/Lava/Irish Coffee. Low Stock. On sale for $171.00. MSRP $190.00. 10% off. 5.0 out of 5 stars

Low Stock

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Black Stamped/Lava/Irish Coffee
Price: $171.00MSRP: $190.00

Cole Haan - Davies Grand Penny Driving Loafers. Color Madeira/Black. Low Stock. On sale for $135.00. MSRP $150.00. 10% off.

Low Stock

Cole Haan Davies Grand Penny Driving Loafers

Cole Haan Davies Grand Penny Driving Loafers

Brand Name: Cole Haan
Product Name: Davies Grand Penny Driving Loafers
Gender: Men's
Color: Madeira/Black
Price: $135.00MSRP: $150.00

Cole Haan - Brower Penny Loafers. Color Woodbury/Gum Water Resistant. On sale for $144.00. MSRP $160.00. 10% off.

Cole Haan Brower Penny Loafers

Cole Haan Brower Penny Loafers

Brand Name: Cole Haan
Product Name: Brower Penny Loafers
Gender: Men's
Color: Woodbury/Gum Water Resistant
Price: $144.00MSRP: $160.00

Cole Haan - Nantucket Penny. Color China Blue Suede/Biscuit/Ivory. On sale for $90.00. MSRP $100.00. 10% off. 3.0 out of 5 stars

Cole Haan Nantucket Penny

Cole Haan Nantucket Penny

Brand Name: Cole Haan
Product Name: Nantucket Penny
Gender: Men's
Color: China Blue Suede/Biscuit/Ivory
Price: $90.00MSRP: $100.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Lava Smoke Stamped/Lava/Dove. On sale for $161.50. MSRP $190.00. 15% off. 5.0 out of 5 stars

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Lava Smoke Stamped/Lava/Dove
Price: $161.50MSRP: $190.00

Cole Haan - Pinch Weekender Penny. Color British Tan/Angora. On sale for $90.00. MSRP $120.00. 25% off. 4.2 out of 5 stars

Cole Haan Pinch Weekender Penny

Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: British Tan/Angora
Price: $90.00MSRP: $120.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color British Tan/Natural Tan/Ivory. Low Stock. On sale for $119.95. MSRP $190.00. 37% off. 5.0 out of 5 stars

Low Stock

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: British Tan/Natural Tan/Ivory
Price: $119.95MSRP: $190.00

Cole Haan - Pinch Weekender Penny. Color Big Dipper Nubuck/Angora. On sale for $79.25. MSRP $130.00. 39% off. 4.2 out of 5 stars

Cole Haan Pinch Weekender Penny

Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: Big Dipper Nubuck/Angora
Price: $79.25MSRP: $130.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Black/Natural Tan/Ivory. On sale for $113.15. MSRP $190.00. 40% off. 5.0 out of 5 stars

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Black/Natural Tan/Ivory
Price: $113.15MSRP: $190.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Big Dipper Nubuck/Natural Tan/Ivory. On sale for $109.95. MSRP $190.00. 42% off. 5.0 out of 5 stars

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Big Dipper Nubuck/Natural Tan/Ivory
Price: $109.95MSRP: $190.00

Cole Haan - Zerogrand Remastered Penny Loafer. Color Dark Latte Nubuck/Natural Tan/Ivory. On sale for $111.09. MSRP $190.00. 42% off. 5.0 out of 5 stars

Cole Haan Zerogrand Remastered Penny Loafer

Cole Haan Zerogrand Remastered Penny Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Penny Loafer
Gender: Men's
Color: Dark Latte Nubuck/Natural Tan/Ivory
Price: $111.09MSRP: $190.00

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Sea Stone/Natural/Ivory. On sale for $138.06. MSRP $170.00. 19% off.

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Sea Stone/Natural/Ivory
Price: $138.06MSRP: $170.00

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Sesame/Brit Tan/Ivory. Low Stock. On sale for $102.12. MSRP $170.00. 40% off.

Low Stock

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Sesame/Brit Tan/Ivory
Price: $102.12MSRP: $170.00

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Navy Blazer/Brit Tan/Ivory. On sale for $100.72. MSRP $170.00. 41% off.

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Navy Blazer/Brit Tan/Ivory
Price: $100.72MSRP: $170.00

Cole Haan - American Classics Hampton Loafer. Color Golden Toffee Nubuck/Angora. Low Stock. On sale for $126.00. MSRP $140.00. 10% off. 3.5 out of 5 stars

Low Stock

Cole Haan American Classics Hampton Loafer

Cole Haan American Classics Hampton Loafer

Brand Name: Cole Haan
Product Name: American Classics Hampton Loafer
Gender: Men's
Color: Golden Toffee Nubuck/Angora
Price: $126.00MSRP: $140.00

Cole Haan - American Classics Hampton Loafer. Color Birchbeige Suede/Angora. Low Stock. On sale for $126.00. MSRP $140.00. 10% off. 3.5 out of 5 stars

Low Stock

Cole Haan American Classics Hampton Loafer

Cole Haan American Classics Hampton Loafer

Brand Name: Cole Haan
Product Name: American Classics Hampton Loafer
Gender: Men's
Color: Birchbeige Suede/Angora
Price: $126.00MSRP: $140.00

SWIMS - Lux Driver. Color Shadow. Low Stock. On sale for $112.50. MSRP $225.00. 50% off.

Low Stock

SWIMS Lux Driver

SWIMS Lux Driver

Brand Name: SWIMS
Product Name: Lux Driver
Gender: Men's
Color: Shadow
Price: $112.50MSRP: $225.00