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Boots on Sale $50 & Under

Shop Boots Deals

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Size 9.5 Medium Size Leather Outsole Shoes

27 items found

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Cole Haan - Pinch Weekender Venetians. Color China Blue Suede/Ivory. On sale for $65.00. MSRP $130.00. 50% off.

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: China Blue Suede/Ivory
Price: $65MSRP: $130

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $78.48. MSRP $110.00. 29% off. 5.0 out of 5 stars

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Perforated Lace To Toe Sneakers
Gender: Men's
Color: Navy Blazer
Price: $78.48MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $76.96. MSRP $110.00. 30% off. 5.0 out of 5 stars

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Perforated Lace To Toe Sneakers
Gender: Men's
Color: Ivory/Black
Price: $76.96MSRP: $110

Frye - Connor Venetian. Color Driftwood. Low Stock. On sale for $47.40. MSRP $158.00. 70% off. 3.5 out of 5 stars

Low Stock

Frye Connor Venetian

Frye Connor Venetian

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Driftwood
Price: $47.40MSRP: $158

TOMS - Travel Lite Forrest. Color Tan. On sale for $58.50. MSRP $130.00. 55% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Tan
Price: $58.50MSRP: $130

COACH - Cooper Loafer. Color Black. $275.00.

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black
Price: $275

ECCO - Classic Tie Sneakers. Color Mink. On sale for $107.95. MSRP $119.95. 10% off. 4.0 out of 5 stars

ECCO Classic Tie Sneakers

ECCO Classic Tie Sneakers

Brand Name: ECCO
Product Name: Classic Tie Sneakers
Gender: Men's
Color: Mink
Price: $107.95MSRP: $119.95

Stacy Adams - Tallero Lace-Up. Color Black/Gray. Low Stock. On sale for $77.42. MSRP $115.00. 33% off. 4.8 out of 5 stars

Low Stock

Stacy Adams Tallero Lace-Up

Stacy Adams Tallero Lace-Up

Brand Name: Stacy Adams
Product Name: Tallero Lace-Up
Gender: Men's
Color: Black/Gray
Price: $77.42MSRP: $115

Stacy Adams - Gabardo Bike Toe Lace-Up. Color Blue. On sale for $105.10. MSRP $115.00. 9% off. 4.8 out of 5 stars

Stacy Adams Gabardo Bike Toe Lace-Up

Stacy Adams Gabardo Bike Toe Lace-Up

Brand Name: Stacy Adams
Product Name: Gabardo Bike Toe Lace-Up
Gender: Men's
Color: Blue
Price: $105.10MSRP: $115

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $81.48. MSRP $110.00. 26% off.

Cole Haan Grand Crosscourt Modern Runner

Cole Haan Grand Crosscourt Modern Runner

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Runner
Gender: Men's
Color: Pavement/Biscuit/Storm Cloud
Price: $81.48MSRP: $110

Stacy Adams - Valet Velour Slip-On Loafer. Color Dark Blue. Low Stock. On sale for $66.60. MSRP $105.00. 37% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Valet Velour Slip-On Loafer

Stacy Adams Valet Velour Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Valet Velour Slip-On Loafer
Gender: Men's
Color: Dark Blue
Price: $66.60MSRP: $105

Stacy Adams - Valet Velour Slip-On Loafer. Color Burgundy. On sale for $81.26. MSRP $105.00. 23% off. 4.5 out of 5 stars

Stacy Adams Valet Velour Slip-On Loafer

Stacy Adams Valet Velour Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Valet Velour Slip-On Loafer
Gender: Men's
Color: Burgundy
Price: $81.26MSRP: $105

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $83.26. MSRP $110.00. 24% off.

Cole Haan Grand Crosscourt Modern Runner

Cole Haan Grand Crosscourt Modern Runner

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Runner
Gender: Men's
Color: Microchip/Quiet Shade/Optic White
Price: $83.26MSRP: $110

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. On sale for $101.07. MSRP $130.00. 22% off. 3.0 out of 5 stars

Cole Haan Grand Hurrion Stitchlite Plain Toe Oxfords

Cole Haan Grand Hurrion Stitchlite Plain Toe Oxfords

Brand Name: Cole Haan
Product Name: Grand Hurrion Stitchlite Plain Toe Oxfords
Gender: Men's
Color: Black/Nimbus/Cloud Ivory
Price: $101.07MSRP: $130

Bruno Magli - Alessio. Color Black. Low Stock. On sale for $197.50. MSRP $395.00. 50% off.

Low Stock

Bruno Magli Alessio

Bruno Magli Alessio

Brand Name: Bruno Magli
Product Name: Alessio
Gender: Men's
Color: Black
Price: $197.50MSRP: $395

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $76.64. MSRP $115.00. 33% 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: $76.64MSRP: $115

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $77.83. MSRP $110.00. 29% off. 5.0 out of 5 stars

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Perforated Lace To Toe Sneakers
Gender: Men's
Color: Black/Ivory
Price: $77.83MSRP: $110

PUMA - Royale. Color Puma White/Deep Navy/Team Light Blue. On sale for $112.00. MSRP $160.00. 30% off.

PUMA Royale

PUMA Royale

Brand Name: PUMA
Product Name: Royale
Gender: Men's
Color: Puma White/Deep Navy/Team Light Blue
Price: $112MSRP: $160

Cole Haan - Original Grand Tour Golf Waterproof. Color Birch Beige/Cinnabar/Ivory Wp. On sale for $188.83. MSRP $210.00. 10% off.

Cole Haan Original Grand Tour Golf Waterproof

Cole Haan Original Grand Tour Golf Waterproof

Brand Name: Cole Haan
Product Name: Original Grand Tour Golf Waterproof
Gender: Men's
Color: Birch Beige/Cinnabar/Ivory Wp
Price: $188.83MSRP: $210

Cole Haan - Grandpro Luxe Wholecut Sneakers. Color Optic White/Optic White. On sale for $162.00. MSRP $180.00. 10% off. 5.0 out of 5 stars

Cole Haan Grandpro Luxe Wholecut Sneakers

Cole Haan Grandpro Luxe Wholecut Sneakers

Brand Name: Cole Haan
Product Name: Grandpro Luxe Wholecut Sneakers
Gender: Men's
Color: Optic White/Optic White
Price: $162MSRP: $180

Cole Haan - Og Energyweave Wingtip Oxfords. Color Golden Toffee Nubuck/China Blue/Ivory. On sale for $130.65. MSRP $170.00. 23% off.

Cole Haan Og Energyweave Wingtip Oxfords

Cole Haan Og Energyweave Wingtip Oxfords

Brand Name: Cole Haan
Product Name: Og Energyweave Wingtip Oxfords
Gender: Men's
Color: Golden Toffee Nubuck/China Blue/Ivory
Price: $130.65MSRP: $170

Cole Haan - Pinch Weekender Venetians. Color Dark Chocolate/Angora. On sale for $78.34. MSRP $130.00. 40% off.

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: Dark Chocolate/Angora
Price: $78.34MSRP: $130

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $122.44. MSRP $155.00. 21% off.

Cole Haan Grandpro Ashland 2 Golf

Cole Haan Grandpro Ashland 2 Golf

Brand Name: Cole Haan
Product Name: Grandpro Ashland 2 Golf
Gender: Men's
Color: Navy Blazer/Titanium/Ivory
Price: $122.44MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $120.87. MSRP $155.00. 22% off.

Cole Haan Grandpro Ashland 2 Golf

Cole Haan Grandpro Ashland 2 Golf

Brand Name: Cole Haan
Product Name: Grandpro Ashland 2 Golf
Gender: Men's
Color: Black/New Caramel/Ivory
Price: $120.87MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $121.16. MSRP $160.00. 24% off.

Cole Haan Grandpro Ashland 2 Golf

Cole Haan Grandpro Ashland 2 Golf

Brand Name: Cole Haan
Product Name: Grandpro Ashland 2 Golf
Gender: Men's
Color: Optic White/Glacier Gray/Ivory
Price: $121.16MSRP: $160

TOMS - Travel Lite Forrest. Color Brown. On sale for $78.00. MSRP $130.00. 40% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $78MSRP: $130

Vans - MTE Ultrarange 2.0 RW. Color Bright Orange. On sale for $70.00. MSRP $100.00. 30% off. 4.0 out of 5 stars

Vans MTE Ultrarange 2.0 RW

Vans MTE Ultrarange 2.0 RW

Brand Name: Vans
Product Name: MTE Ultrarange 2.0 RW
Gender: Unisex
Color: Bright Orange
Price: $70MSRP: $100