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Boots on Sale $50 & Under

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Size 8 Leather Outsole Comfort Shoes

30 items found

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Frye - Connor Venetian. Color Black. 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: Black
Price: $47.40MSRP: $158

Bruno Magli - Arlo. Color White. Low Stock. On sale for $158.00. MSRP $395.00. 60% off.

Low Stock

Bruno Magli Arlo

Bruno Magli Arlo

Brand Name: Bruno Magli
Product Name: Arlo
Gender: Men's
Color: White
Price: $158MSRP: $395

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $77.24. 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: $77.24MSRP: $110

Massimo Matteo - Suede Lace-Up Oxford Classic. Color Cafe. Low Stock. On sale for $34.48. MSRP $114.95. 70% off. 2.0 out of 5 stars

Low Stock

Massimo Matteo Suede Lace-Up Oxford Classic

Massimo Matteo Suede Lace-Up Oxford Classic

Brand Name: Massimo Matteo
Product Name: Suede Lace-Up Oxford Classic
Gender: Men's
Color: Cafe
Price: $34.48MSRP: $114.95

Cole Haan - Original Grand 2.0. Color Big Dipper Nubuck/Ancient Scroll. On sale for $115.00. MSRP $230.00. 50% off.

Cole Haan Original Grand 2.0

Cole Haan Original Grand 2.0

Brand Name: Cole Haan
Product Name: Original Grand 2.0
Gender: Men's
Color: Big Dipper Nubuck/Ancient Scroll
Price: $115MSRP: $230

HUGO BOSS - Colby Smooth Leather Derby Dress Shoes. Color Burnt Caramel. Low Stock. $199.00.

Low Stock

HUGO BOSS Colby Smooth Leather Derby Dress Shoes

HUGO BOSS Colby Smooth Leather Derby Dress Shoes

Brand Name: HUGO BOSS
Product Name: Colby Smooth Leather Derby Dress Shoes
Gender: Men's
Color: Burnt Caramel
Price: $199

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $80.87. MSRP $110.00. 26% 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: $80.87MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $77.79. 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: $77.79MSRP: $110

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Quiet Shade. On sale for $81.59. MSRP $110.00. 26% 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: $81.59MSRP: $110

Born - Cambridge. Color Dark Brown (Braken). Low Stock. On sale for $54.00. MSRP $135.00. 60% off.

Low Stock

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Dark Brown (Braken)
Price: $54MSRP: $135

Born - Cambridge. Color Black. Low Stock. On sale for $65.00. MSRP $135.00. 52% off.

Low Stock

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Black
Price: $65MSRP: $135

Johnston & Murphy - Taylor Penny. Color Denim. Low Stock. On sale for $178.80. MSRP $298.00. 40% 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: $178.80MSRP: $298

Vans - MTE Ultrarange Neo VR3. Color Marshmallow. On sale for $106.25. MSRP $125.00. 15% off.

Vans MTE Ultrarange Neo VR3

Vans MTE Ultrarange Neo VR3

Brand Name: Vans
Product Name: MTE Ultrarange Neo VR3
Gender: Unisex
Color: Marshmallow
Price: $106.25MSRP: $125

Vans - MTE Ultrarange 2.0 RW. Color True White. On sale for $55.00. MSRP $100.00. 45% 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: True White
Price: $55MSRP: $100

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. On sale for $102.57. MSRP $130.00. 21% 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: $102.57MSRP: $130

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $85.02. MSRP $110.00. 23% 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: $85.02MSRP: $110

Cole Haan - Og Energyweave Wingtip Oxfords. Color Golden Toffee Nubuck/China Blue/Ivory. On sale for $132.77. MSRP $170.00. 22% 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: $132.77MSRP: $170

Cole Haan - Pinch Weekender Venetians. Color Dark Chocolate/Angora. On sale for $78.52. 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: $78.52MSRP: $130

Marc Joseph New York - Hamilton Pl. Color Whiskey Brushed Napa. 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: Whiskey Brushed Napa
Price: $52.50MSRP: $175

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

Cole Haan - Original Grand Tour Golf Waterproof. Color Birch Beige/Cinnabar/Ivory Wp. On sale for $186.93. MSRP $210.00. 11% 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: $186.93MSRP: $210

Cole Haan - American Classics Montrose Plain Toe Ox. Color Titanium Nubuck/Angora. Low Stock. On sale for $95.00. MSRP $190.00. 50% 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: Titanium Nubuck/Angora
Price: $95MSRP: $190

Johnston & Murphy - Cormac Cap Toe. Color Black Italian Calfskin. Low Stock. On sale for $221.25. MSRP $295.00. 25% off. 4.7 out of 5 stars

Low Stock

Johnston & Murphy Cormac Cap Toe

Johnston & Murphy Cormac Cap Toe

Brand Name: Johnston & Murphy
Product Name: Cormac Cap Toe
Gender: Men's
Color: Black Italian Calfskin
Price: $221.25MSRP: $295

Stacy Adams - Gabardo Bike Toe Lace-Up. Color Blue. On sale for $105.10. MSRP $115.00. 9% off. 5.0 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 - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $123.28. MSRP $155.00. 20% 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: $123.28MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $125.06. 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: $125.06MSRP: $160

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $124.91. MSRP $155.00. 19% 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: $124.91MSRP: $155

Stacy Adams - Tallero Lace-Up. Color Dark Blue Multi. Low Stock. $115.00. 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: $115

Stacy Adams - Tallero Lace-Up. Color Tan Multi. Low Stock. On sale for $80.94. MSRP $115.00. 30% 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: $80.94MSRP: $115

ECCO - Classic Tie Sneakers. Color Mink. Low Stock. On sale for $107.95. MSRP $119.95. 10% off. 4.0 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: $107.95MSRP: $119.95