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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Size 8.5 Leather Outsole On Sale Products

22 items found

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Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $78.17. 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: $78.17MSRP: $110

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $128.74. MSRP $155.00. 17% off. 5.0 out of 5 stars

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: $128.74MSRP: $155

TOMS - Travel Lite Forrest. Color Brown. On sale for $65.00. MSRP $130.00. 50% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $65MSRP: $130

Frye - Connor Venetian. Color Black. On sale for $79.00. MSRP $158.00. 50% off. 3.5 out of 5 stars

Frye Connor Venetian

Frye Connor Venetian

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Black
Price: $79MSRP: $158

Stacy Adams - Valet Velour Slip-On Loafer. Color Burgundy. On sale for $74.65. MSRP $105.00. 29% 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: $74.65MSRP: $105

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $88.88. 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: $88.88MSRP: $110

Stacy Adams - Valet Velour Slip-On Loafer. Color Dark Blue. Low Stock. On sale for $65.06. MSRP $105.00. 38% 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: $65.06MSRP: $105

Cole Haan - Grand Laser Bit Drivers. Color Golden Toffee Nubuck/Gum. Low Stock. On sale for $90.00. MSRP $150.00. 40% 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: $90MSRP: $150

Cole Haan - American Classics Montrose Plain Toe Ox. Color Navy Blazer Nubuck/Angora. On sale for $153.62. MSRP $190.00. 19% 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: $153.62MSRP: $190

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $82.93. MSRP $110.00. 25% 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: $82.93MSRP: $110

Born - Cambridge. Color Dark Brown (Braken). Low Stock. On sale for $121.50. MSRP $135.00. 10% off.

Low Stock

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Dark Brown (Braken)
Price: $121.50MSRP: $135

ECCO - Classic Tie Sneakers. Color Mink. Low Stock. On sale for $89.96. MSRP $119.95. 25% off. 2.5 out of 5 stars

Low Stock

ECCO Classic Tie Sneakers

ECCO Classic Tie Sneakers

Brand Name: ECCO
Product Name: Classic Tie Sneakers
Gender: Men's
Color: Mink
Price: $89.96MSRP: $119.95

Stacy Adams - Tallero Lace-Up. Color Tan Multi. Low Stock. On sale for $85.80. MSRP $115.00. 25% 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: Tan Multi
Price: $85.80MSRP: $115

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $124.97. MSRP $155.00. 19% off. 5.0 out of 5 stars

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: $124.97MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $125.55. MSRP $160.00. 22% off. 5.0 out of 5 stars

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: $125.55MSRP: $160

Marc Joseph New York - Canal St 2.0. Color Black Napa. Low Stock. On sale for $97.50. MSRP $195.00. 50% off.

Low Stock

Marc Joseph New York Canal St 2.0

Marc Joseph New York Canal St 2.0

Brand Name: Marc Joseph New York
Product Name: Canal St 2.0
Gender: Men's
Color: Black Napa
Price: $97.50MSRP: $195

Stacy Adams - Tallero Lace-Up. Color Dark Blue Multi. Low Stock. On sale for $82.22. MSRP $115.00. 29% 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: Dark Blue Multi
Price: $82.22MSRP: $115

Marc Joseph New York - Hamilton Pl. Color Whiskey Brushed Napa. On sale for $131.25. MSRP $175.00. 25% off.

Marc Joseph New York Hamilton Pl

Marc Joseph New York Hamilton Pl

Brand Name: Marc Joseph New York
Product Name: Hamilton Pl
Gender: Men's
Color: Whiskey Brushed Napa
Price: $131.25MSRP: $175

Marc Joseph New York - Chambers St. Color Black Grainy. On sale for $146.25. MSRP $195.00. 25% off.

Marc Joseph New York Chambers St

Marc Joseph New York Chambers St

Brand Name: Marc Joseph New York
Product Name: Chambers St
Gender: Men's
Color: Black Grainy
Price: $146.25MSRP: $195

Marc Joseph New York - Hamilton Pl. Color Black Grainy. On sale for $105.00. MSRP $175.00. 40% off.

Marc Joseph New York Hamilton Pl

Marc Joseph New York Hamilton Pl

Brand Name: Marc Joseph New York
Product Name: Hamilton Pl
Gender: Men's
Color: Black Grainy
Price: $105MSRP: $175

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $77.91. 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: Ivory/Black
Price: $77.91MSRP: $110

Marc Joseph New York - BROADWAY. Color Navy Suede. On sale for $132.00. MSRP $165.00. 20% off.

Marc Joseph New York BROADWAY

Marc Joseph New York BROADWAY

Brand Name: Marc Joseph New York
Product Name: BROADWAY
Gender: Men's
Color: Navy Suede
Price: $132MSRP: $165