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Boots on Sale $50 & Under

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Size 9.5 Leather Outsole Round Toe Products

31 items found

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Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $78.61. 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: $78.61MSRP: $110

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $78.36. 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: $78.36MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $73.84. MSRP $110.00. 33% 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: $73.84MSRP: $110

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

Vans - MTE Ultrarange 2.0 RW. Color Bright Orange. On sale for $80.00. MSRP $100.00. 20% off. 3.5 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: $80MSRP: $100

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $83.42. 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: $83.42MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $85.54. MSRP $110.00. 22% 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: $85.54MSRP: $110

Cole Haan - American Classics Montrose Plain Toe Ox. Color Light Sesame Suede/Birch Beige/Ivory. Low Stock. On sale for $107.07. MSRP $190.00. 44% off. 5.0 out of 5 stars

Low Stock

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: Light Sesame Suede/Birch Beige/Ivory
Price: $107.07MSRP: $190

Cole Haan - Original Grand Tour Golf Waterproof. Color Birch Beige/Cinnabar/Ivory Wp. On sale for $149.95. MSRP $210.00. 29% 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: $149.95MSRP: $210

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

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 $133.78. MSRP $170.00. 21% 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: $133.78MSRP: $170

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

Cole Haan - Pinch Weekender Venetians. Color China Blue Suede/Ivory. On sale for $96.64. MSRP $130.00. 26% 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: $96.64MSRP: $130

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

Stacy Adams - Valet Velour Slip-On Loafer. Color Dark Blue. Low Stock. On sale for $68.85. 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: $68.85MSRP: $105

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Navy Blazer/Silver Birch/Ivory. On sale for $97.50. MSRP $130.00. 25% 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: Navy Blazer/Silver Birch/Ivory
Price: $97.50MSRP: $130

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. On sale for $97.40. MSRP $130.00. 25% 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: $97.40MSRP: $130

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

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $119.34. MSRP $155.00. 23% 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: $119.34MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $117.01. MSRP $155.00. 25% 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: $117.01MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $124.34. MSRP $160.00. 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: Optic White/Glacier Gray/Ivory
Price: $124.34MSRP: $160

Bruno Magli - Alessio. Color Black. Low Stock. On sale for $217.25. MSRP $395.00. 45% off.

Low Stock

Bruno Magli Alessio

Bruno Magli Alessio

Brand Name: Bruno Magli
Product Name: Alessio
Gender: Men's
Color: Black
Price: $217.25MSRP: $395

Gordon Rush - Austin. Color Espresso. Low Stock. On sale for $79.50. MSRP $96.00. 17% off. 3.0 out of 5 stars

Low Stock

Gordon Rush Austin

Gordon Rush Austin

Brand Name: Gordon Rush
Product Name: Austin
Gender: Men's
Color: Espresso
Price: $79.50MSRP: $96

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

Marc Joseph New York - Hamilton Pl. Color Black Grainy. Low Stock. On sale for $52.50. MSRP $175.00. 70% off.

Low Stock

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: $52.50MSRP: $175

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $86.57. MSRP $115.00. 25% 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: $86.57MSRP: $115

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 - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Quiet Shade. On sale for $77.55. 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: Quiet Shade
Price: $77.55MSRP: $110

Steve Madden - Possess. Color White 1. $119.99. 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: $119.99

Bruno Magli - Maioco Penny. Color Brown. Low Stock. On sale for $276.50. MSRP $395.00. 30% off.

Low Stock

Bruno Magli Maioco Penny

Bruno Magli Maioco Penny

Brand Name: Bruno Magli
Product Name: Maioco Penny
Gender: Men's
Color: Brown
Price: $276.50MSRP: $395

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