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Boots on Sale $50 & Under

Shop Boots Deals

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Size 8.5 Leather Outsole Round Toe Shoes On Sale

23 items found

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Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $84.09. MSRP $110.00. 24% 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: $84.09MSRP: $110

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $133.13. MSRP $160.00. 17% 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: $133.13MSRP: $160

Cole Haan - Grand Laser Bit Drivers. Color Golden Toffee Nubuck/Gum. Low Stock. On sale for $120.37. MSRP $150.00. 20% off.

Low Stock

Cole Haan Grand Laser Bit Drivers

Cole Haan Grand Laser Bit Drivers

Brand Name: Cole Haan
Product Name: Grand Laser Bit Drivers
Gender: Men's
Color: Golden Toffee Nubuck/Gum
Price: $120.37MSRP: $150

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

Johnston & Murphy - Taylor Penny. Color Denim. Low Stock. On sale for $193.70. MSRP $298.00. 35% off. 4.8 out of 5 stars

Low Stock

Johnston & Murphy Taylor Penny

Johnston & Murphy Taylor Penny

Brand Name: Johnston & Murphy
Product Name: Taylor Penny
Gender: Men's
Color: Denim
Price: $193.70MSRP: $298

Stacy Adams - Valet Velour Slip-On Loafer. Color Dark Blue. Low Stock. On sale for $68.88. MSRP $105.00. 34% 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: $68.88MSRP: $105

Stacy Adams - Valet Velour Slip-On Loafer. Color Burgundy. On sale for $81.32. 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: $81.32MSRP: $105

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $89.37. MSRP $110.00. 19% 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: $89.37MSRP: $110

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $77.60. MSRP $110.00. 29% 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: $77.60MSRP: $110

Vans - Lowland 2.0. Color Sun/Dried Tomato. Low Stock. On sale for $42.50. MSRP $85.00. 50% off. 5.0 out of 5 stars

Low Stock

Vans Lowland 2.0

Vans Lowland 2.0

Brand Name: Vans
Product Name: Lowland 2.0
Gender: Unisex
Color: Sun/Dried Tomato
Price: $42.50MSRP: $85

Magnanni - Borazo. Color Taupe/Grey. Low Stock. On sale for $374.25. MSRP $499.00. 25% off.

Low Stock

Magnanni Borazo

Magnanni Borazo

Brand Name: Magnanni
Product Name: Borazo
Gender: Men's
Color: Taupe/Grey
Price: $374.25MSRP: $499

PUMA - Royale. Color Puma White/Deep Navy/Team Light Blue. On sale for $119.99. MSRP $160.00. 25% off.

PUMA Royale

PUMA Royale

Brand Name: PUMA
Product Name: Royale
Gender: Men's
Color: Puma White/Deep Navy/Team Light Blue
Price: $119.99MSRP: $160

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $131.97. MSRP $155.00. 15% 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: $131.97MSRP: $155

Vans - MTE Ultrarange Neo VR3. Color Dark Brown. On sale for $112.50. MSRP $125.00. 10% off.

Vans MTE Ultrarange Neo VR3

Vans MTE Ultrarange Neo VR3

Brand Name: Vans
Product Name: MTE Ultrarange Neo VR3
Gender: Unisex
Color: Dark Brown
Price: $112.50MSRP: $125

Gordon Rush - Cooper. Color Grey. Low Stock. On sale for $67.96. MSRP $169.90. 60% off. 2.0 out of 5 stars

Low Stock

Gordon Rush Cooper

Gordon Rush Cooper

Brand Name: Gordon Rush
Product Name: Cooper
Gender: Men's
Color: Grey
Price: $67.96MSRP: $169.90

Cole Haan - Grandpro Luxe Slip-On Sneakers. Color Ivory/Microchip/Ivory. Low Stock. On sale for $119.00. MSRP $170.00. 30% off. 4.0 out of 5 stars

Low Stock

Cole Haan Grandpro Luxe Slip-On Sneakers

Cole Haan Grandpro Luxe Slip-On Sneakers

Brand Name: Cole Haan
Product Name: Grandpro Luxe Slip-On Sneakers
Gender: Men's
Color: Ivory/Microchip/Ivory
Price: $119MSRP: $170

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $130.17. MSRP $155.00. 16% 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: $130.17MSRP: $155

Cole Haan - Grandpro Luxe Slip-On Sneakers. Color Spiced Brown Suede/Raven/Ivory. Low Stock. On sale for $153.00. MSRP $170.00. 10% off. 4.0 out of 5 stars

Low Stock

Cole Haan Grandpro Luxe Slip-On Sneakers

Cole Haan Grandpro Luxe Slip-On Sneakers

Brand Name: Cole Haan
Product Name: Grandpro Luxe Slip-On Sneakers
Gender: Men's
Color: Spiced Brown Suede/Raven/Ivory
Price: $153MSRP: $170

Bruno Magli - Arlo. Color Black Tumbled. Low Stock. On sale for $276.50. MSRP $395.00. 30% off.

Low Stock

Bruno Magli Arlo

Bruno Magli Arlo

Brand Name: Bruno Magli
Product Name: Arlo
Gender: Men's
Color: Black Tumbled
Price: $276.50MSRP: $395

Cole Haan - American Classics Montrose Plain Toe Ox. Color Navy Blazer Nubuck/Angora. On sale for $171.00. MSRP $190.00. 10% off. 5.0 out of 5 stars

Cole Haan American Classics Montrose Plain Toe Ox

Cole Haan American Classics Montrose Plain Toe Ox

Brand Name: Cole Haan
Product Name: American Classics Montrose Plain Toe Ox
Gender: Men's
Color: Navy Blazer Nubuck/Angora
Price: $171MSRP: $190

Cole Haan - Pinch Weekender Venetians. Color Black/Angora. On sale for $97.50. MSRP $130.00. 25% off.

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: Black/Angora
Price: $97.50MSRP: $130

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $88.10. MSRP $110.00. 20% 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: $88.10MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Quiet Shade. On sale for $79.83. MSRP $110.00. 27% 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: Quiet Shade
Price: $79.83MSRP: $110