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Boots on Sale $50 & Under

Shop Boots Deals

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Medium Size Leather Outsole Round Toe Products

45 items found

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Glerups - Wool Slip-On Leather Outsole. Color Denim. On sale for $70.00. MSRP $100.00. 30% off. 4.5 out of 5 stars

Glerups Wool Slip-On Leather Outsole

Glerups Wool Slip-On Leather Outsole

Brand Name: Glerups
Product Name: Wool Slip-On Leather Outsole
Gender: Unisex
Color: Denim
Price: $70MSRP: $100

Vans - Classic Slip-On Checkerboard. Color Checkerboard Crystal Blue. On sale for $45.50. MSRP $65.00. 30% off. 4.6 out of 5 stars

Vans Classic Slip-On Checkerboard

Vans Classic Slip-On Checkerboard

Brand Name: Vans
Product Name: Classic Slip-On Checkerboard
Gender: Unisex
Color: Checkerboard Crystal Blue
Price: $45.50MSRP: $65

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. 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: Ivory/Black
Price: $78.17MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $82.50. MSRP $110.00. 25% 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: $82.50MSRP: $110

Vans - Hylane. Color Retro Skate Navy. On sale for $58.50. MSRP $90.00. 35% off.

Vans Hylane

Vans Hylane

Brand Name: Vans
Product Name: Hylane
Gender: Unisex
Color: Retro Skate Navy
Price: $58.50MSRP: $90

Vans - MTE Ultrarange 2.0 RW. Color Bright Yellow. On sale for $40.00. MSRP $100.00. 60% off. 3.3 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 Yellow
Price: $40MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Dress Blues. On sale for $80.00. MSRP $100.00. 20% off. 3.3 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: Dress Blues
Price: $80MSRP: $100

Marc Joseph New York - Highland Pl Boot. Color Black Grainy. Low Stock. On sale for $78.00. MSRP $195.00. 60% off.

Low Stock

Marc Joseph New York Highland Pl Boot

Marc Joseph New York Highland Pl Boot

Brand Name: Marc Joseph New York
Product Name: Highland Pl Boot
Gender: Men's
Color: Black Grainy
Price: $78MSRP: $195

Tommy Hilfiger - Rosell. Color Brown. On sale for $39.98. MSRP $79.95. 50% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Brown
Price: $39.98MSRP: $79.95

Tommy Hilfiger - Rosell. Color Medium Brown. Low Stock. On sale for $71.95. MSRP $79.95. 10% off.

Low Stock

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Medium Brown
Price: $71.95MSRP: $79.95

Tommy Hilfiger - Rosell. Color Black. On sale for $39.98. MSRP $79.95. 50% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Black
Price: $39.98MSRP: $79.95

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. On sale for $95.44. MSRP $130.00. 27% off.

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: $95.44MSRP: $130

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Quiet Shade. On sale for $82.45. MSRP $110.00. 25% 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: $82.45MSRP: $110

Marc Joseph New York - BROADWAY. Color Café Croco. Low Stock. On sale for $74.25. MSRP $165.00. 55% off.

Low Stock

Marc Joseph New York BROADWAY

Marc Joseph New York BROADWAY

Brand Name: Marc Joseph New York
Product Name: BROADWAY
Gender: Men's
Color: Café Croco
Price: $74.25MSRP: $165

COACH - Cooper Loafer. Color Saddle. Low Stock. On sale for $68.75. MSRP $275.00. 75% off.

Low Stock

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Saddle
Price: $68.75MSRP: $275

Nunn Bush - MAC Moccasin Toe Oxford. Color Brown. Low Stock. On sale for $73.97. MSRP $100.00. 26% off. 5.0 out of 5 stars

Low Stock

Nunn Bush MAC Moccasin Toe Oxford

Nunn Bush MAC Moccasin Toe Oxford

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Oxford
Gender: Men's
Color: Brown
Price: $73.97MSRP: $100

Nunn Bush - MAC Moccasin Toe Oxford. Color Black. Low Stock. On sale for $77.78. MSRP $100.00. 22% off. 5.0 out of 5 stars

Low Stock

Nunn Bush MAC Moccasin Toe Oxford

Nunn Bush MAC Moccasin Toe Oxford

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Oxford
Gender: Men's
Color: Black
Price: $77.78MSRP: $100

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

Low Stock

Marc Joseph New York Blake Ave

Marc Joseph New York Blake Ave

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

Stacy Adams - Valet Velour Slip-On Loafer. Color Dark Blue. Low Stock. On sale for $74.57. MSRP $105.00. 29% 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: $74.57MSRP: $105

Tommy Hilfiger - Risten. Color Black. Low Stock. On sale for $35.97. MSRP $79.95. 55% off.

Low Stock

Tommy Hilfiger Risten

Tommy Hilfiger Risten

Brand Name: Tommy Hilfiger
Product Name: Risten
Gender: Men's
Color: Black
Price: $35.97MSRP: $79.95

Gordon Rush - Cooper. Color Grey. Low Stock. On sale for $76.45. MSRP $169.90. 55% 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: $76.45MSRP: $169.90

Cole Haan - Grand Crosscourt Sneakers. Color Light Sesame Nubuck/Ivory. Low Stock. On sale for $99.00. MSRP $110.00. 10% off.

Low Stock

Cole Haan Grand Crosscourt Sneakers

Cole Haan Grand Crosscourt Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt Sneakers
Gender: Men's
Color: Light Sesame Nubuck/Ivory
Price: $99MSRP: $110

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Navy Blazer/Silver Birch/Ivory. On sale for $97.50. MSRP $130.00. 25% off.

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: Navy Blazer/Silver Birch/Ivory
Price: $97.50MSRP: $130

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $88.52. MSRP $110.00. 20% 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: $88.52MSRP: $110

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $86.24. MSRP $110.00. 22% 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: $86.24MSRP: $110

Cole Haan - Grand Remix Knit Oxfords. Color Silver Lining/Acorn/Ivory. Low Stock. On sale for $88.00. MSRP $110.00. 20% off.

Low Stock

Cole Haan Grand Remix Knit Oxfords

Cole Haan Grand Remix Knit Oxfords

Brand Name: Cole Haan
Product Name: Grand Remix Knit Oxfords
Gender: Men's
Color: Silver Lining/Acorn/Ivory
Price: $88MSRP: $110

Calvin Klein - Libra. Color Black. Low Stock. On sale for $49.50. MSRP $99.00. 50% off.

Low Stock

Calvin Klein Libra

Calvin Klein Libra

Brand Name: Calvin Klein
Product Name: Libra
Gender: Men's
Color: Black
Price: $49.50MSRP: $99

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $89.98. MSRP $110.00. 18% 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: $89.98MSRP: $110

Steve Madden - Possess. Color White 1. On sale for $98.06. MSRP $120.00. 18% off. 3.0 out of 5 stars

Steve Madden Possess

Steve Madden Possess

Brand Name: Steve Madden
Product Name: Possess
Gender: Men's
Color: White 1
Price: $98.06MSRP: $120

Vans - Lowland 2.0. Color Sun/Dried Tomato. On sale for $76.50. MSRP $85.00. 10% off.

Vans Lowland 2.0

Vans Lowland 2.0

Brand Name: Vans
Product Name: Lowland 2.0
Gender: Unisex
Color: Sun/Dried Tomato
Price: $76.50MSRP: $85

Vans - Hylane. Color Retro Skate Lunar Rock. On sale for $58.50. MSRP $90.00. 35% off.

Vans Hylane

Vans Hylane

Brand Name: Vans
Product Name: Hylane
Gender: Unisex
Color: Retro Skate Lunar Rock
Price: $58.50MSRP: $90

Vans - MTE Ultrarange 2.0 RW. Color Black/Multi. On sale for $65.00. MSRP $100.00. 35% off. 3.3 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: Black/Multi
Price: $65MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Brown. On sale for $75.00. MSRP $100.00. 25% off. 3.3 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: Brown
Price: $75MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Mushroom. On sale for $80.00. MSRP $100.00. 20% off. 3.3 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: Mushroom
Price: $80MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Bright Orange. On sale for $90.00. MSRP $100.00. 10% off. 3.3 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: $90MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Bungee Cord. On sale for $90.00. MSRP $100.00. 10% off. 3.3 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: Bungee Cord
Price: $90MSRP: $100

Vans - MTE Crosspath Mid. Color Dark Green/Dark Brown. On sale for $98.00. MSRP $140.00. 30% off. 5.0 out of 5 stars

Vans MTE Crosspath Mid

Vans MTE Crosspath Mid

Brand Name: Vans
Product Name: MTE Crosspath Mid
Gender: Unisex
Color: Dark Green/Dark Brown
Price: $98MSRP: $140

Johnston & Murphy - Baldwin Tassel. Color Brown. Low Stock. On sale for $87.75. MSRP $195.00. 55% off.

Low Stock

Johnston & Murphy Baldwin Tassel

Johnston & Murphy Baldwin Tassel

Brand Name: Johnston & Murphy
Product Name: Baldwin Tassel
Gender: Men's
Color: Brown
Price: $87.75MSRP: $195

Frye - Connor Venetian. Color Chocolate. Low Stock. On sale for $84.00. MSRP $168.00. 50% off. 4.0 out of 5 stars

Low Stock

Frye Connor Venetian

Frye Connor Venetian

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Chocolate
Price: $84MSRP: $168

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 - Pinch Weekender Venetians. Color British Tan/Angora. On sale for $78.08. 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: British Tan/Angora
Price: $78.08MSRP: $130

Vans - MTE Ultrarange 2.0 RW. Color Sepia Rose. On sale for $55.00. MSRP $100.00. 45% off. 3.3 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: Sepia Rose
Price: $55MSRP: $100

Cole Haan - Pinch Weekender Venetians. Color Dark Chocolate/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: Dark Chocolate/Angora
Price: $97.50MSRP: $130

Frye - Connor Venetian. Color Driftwood. On sale for $63.20. MSRP $158.00. 60% off. 4.0 out of 5 stars

Frye Connor Venetian

Frye Connor Venetian

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Driftwood
Price: $63.20MSRP: $158

Frye - Connor Venetian. Color Black. On sale for $94.80. MSRP $158.00. 40% off. 4.0 out of 5 stars

Frye Connor Venetian

Frye Connor Venetian

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Black
Price: $94.80MSRP: $158