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Boots on Sale $50 & Under

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Men's Size 8.5 Leather Outsole Comfort Products

27 items found

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Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $78.89. MSRP $110.00. 28% 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: $78.89MSRP: $110

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $127.54. MSRP $155.00. 18% 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: $127.54MSRP: $155

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Navy Blazer. On sale for $77.20. 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: Navy Blazer
Price: $77.20MSRP: $110

TOMS - Travel Lite Forrest. Color Brown. On sale for $65.00. MSRP $130.00. 50% off. 5.0 out of 5 stars

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

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

Marc Joseph New York - Newbury Street (Hands Free Technology). Color Grey Napa Leather. On sale for $134.95. MSRP $149.95. 10% off. 5.0 out of 5 stars

Marc Joseph New York Newbury Street (Hands Free Technology)

Marc Joseph New York Newbury Street (Hands Free Technology)

Brand Name: Marc Joseph New York
Product Name: Newbury Street (Hands Free Technology)
Gender: Men's
Color: Grey Napa Leather
Price: $134.95MSRP: $149.95

Stacy Adams - Tallero Lace-Up. Color Tan Multi. Low Stock. On sale for $91.20. MSRP $115.00. 21% 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: $91.20MSRP: $115

Stacy Adams - Tallero Lace-Up. Color Burgundy Multi. Low Stock. On sale for $87.29. MSRP $115.00. 24% 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: Burgundy Multi
Price: $87.29MSRP: $115

Stacy Adams - Tallero Lace-Up. Color Dark Blue Multi. Low Stock. On sale for $91.26. MSRP $115.00. 21% 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: $91.26MSRP: $115

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $123.76. MSRP $155.00. 20% 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: $123.76MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $124.86. 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: $124.86MSRP: $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

Johnston & Murphy - Cormac Cap Toe. Color Black Italian Calfskin. Low Stock. On sale for $136.00. MSRP $295.00. 54% 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: $136MSRP: $295

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

Stacy Adams - Tristano Bike Toe Lace-Up. Color White. Low Stock. On sale for $105.53. MSRP $115.00. 8% off. 4.6 out of 5 stars

Low Stock

Stacy Adams Tristano Bike Toe Lace-Up

Stacy Adams Tristano Bike Toe Lace-Up

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: White
Price: $105.53MSRP: $115

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

Marc Joseph New York - Harbor Road (Hands Free Technology). Color White Napa Leather. On sale for $119.96. MSRP $149.95. 20% off. 5.0 out of 5 stars

Marc Joseph New York Harbor Road (Hands Free Technology)

Marc Joseph New York Harbor Road (Hands Free Technology)

Brand Name: Marc Joseph New York
Product Name: Harbor Road (Hands Free Technology)
Gender: Men's
Color: White Napa Leather
Price: $119.96MSRP: $149.95

Marc Joseph New York - North Street (Hands Free Technology). Color Cognac Napa Leather. On sale for $111.96. MSRP $159.95. 30% off. 4.5 out of 5 stars

Marc Joseph New York North Street (Hands Free Technology)

Marc Joseph New York North Street (Hands Free Technology)

Brand Name: Marc Joseph New York
Product Name: North Street (Hands Free Technology)
Gender: Men's
Color: Cognac Napa Leather
Price: $111.96MSRP: $159.95

Marc Joseph New York - Newbury Street (Hands Free Technology). Color Black Napa Leather. On sale for $104.96. MSRP $149.95. 30% off. 5.0 out of 5 stars

Marc Joseph New York Newbury Street (Hands Free Technology)

Marc Joseph New York Newbury Street (Hands Free Technology)

Brand Name: Marc Joseph New York
Product Name: Newbury Street (Hands Free Technology)
Gender: Men's
Color: Black Napa Leather
Price: $104.96MSRP: $149.95

ECCO - Classic Tie Sneakers. Color Mink. Low Stock. On sale for $101.95. MSRP $119.95. 15% 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: $101.95MSRP: $119.95

Johnston & Murphy - Jenkins Plain Toe. Color Taupe Nubuck. On sale for $80.91. MSRP $89.90. 10% off. 5.0 out of 5 stars

Johnston & Murphy Jenkins Plain Toe

Johnston & Murphy Jenkins Plain Toe

Brand Name: Johnston & Murphy
Product Name: Jenkins Plain Toe
Gender: Men's
Color: Taupe Nubuck
Price: $80.91MSRP: $89.90

Frye - Connor Venetian. Color Black. On sale for $110.60. MSRP $158.00. 30% 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: $110.60MSRP: $158

Cole Haan - Original Grand Tour Golf Waterproof. Color Birch Beige/Cinnabar/Ivory Wp. On sale for $192.44. MSRP $210.00. 8% 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: $192.44MSRP: $210

Cole Haan - American Classics Montrose Plain Toe Ox. Color Navy Blazer Nubuck/Angora. On sale for $142.48. MSRP $190.00. 25% 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: $142.48MSRP: $190

Vans - MTE Ultrarange 2.0 RW. Color Dress Blues. On sale for $70.00. MSRP $100.00. 30% off. 4.1 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: $70MSRP: $100

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. On sale for $88.92. 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: $88.92MSRP: $110