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Boots on Sale $50 & Under

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Size 9.5 Medium Size Leather Outsole Shoes

55 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

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Ivory/Black. On sale for $78.66. 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: $78.66MSRP: $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 - 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

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 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 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

Johnston & Murphy - Cormac Cap Toe. Color Brown/Tan Italian Calfskin. Low Stock. On sale for $172.42. MSRP $229.90. 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: Brown/Tan Italian Calfskin
Price: $172.42MSRP: $229.90

Tommy Hilfiger - Rosell. Color Black. On sale for $72.61. MSRP $79.95. 9% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Black
Price: $72.61MSRP: $79.95

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

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. On sale for $96.59. MSRP $130.00. 26% 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: $96.59MSRP: $130

Cole Haan - Pinch Weekender Venetians. Color Black/Angora. On sale for $117.00. MSRP $130.00. 10% 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: $117MSRP: $130

Cole Haan - Grandpro Featherarc Bike Toe Sneakers. Color Big Dipper/Sea Stone/Ivory. On sale for $135.00. MSRP $150.00. 10% off. 5.0 out of 5 stars

Cole Haan Grandpro Featherarc Bike Toe Sneakers

Cole Haan Grandpro Featherarc Bike Toe Sneakers

Brand Name: Cole Haan
Product Name: Grandpro Featherarc Bike Toe Sneakers
Gender: Men's
Color: Big Dipper/Sea Stone/Ivory
Price: $135MSRP: $150

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $101.75. MSRP $115.00. 12% 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: $101.75MSRP: $115

Massimo Matteo - Moccasin Loafers. Color Black. Low Stock. On sale for $54.50. MSRP $109.00. 50% off.

Low Stock

Massimo Matteo Moccasin Loafers

Massimo Matteo Moccasin Loafers

Brand Name: Massimo Matteo
Product Name: Moccasin Loafers
Gender: Men's
Color: Black
Price: $54.50MSRP: $109

Johnston & Murphy - Cormac Cap Toe. Color Black Italian Calfskin. On sale for $236.00. MSRP $295.00. 20% off. 4.7 out of 5 stars

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: $236MSRP: $295

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

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

Cole Haan - Grandpro Ashland 2 Golf. Color Navy Blazer/Titanium/Ivory. On sale for $140.53. MSRP $155.00. 9% 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: $140.53MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $129.42. MSRP $155.00. 17% 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: $129.42MSRP: $155

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $134.23. MSRP $160.00. 16% 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: $134.23MSRP: $160

Tommy Hilfiger - Rosell. Color Brown. On sale for $71.56. MSRP $79.95. 10% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Brown
Price: $71.56MSRP: $79.95

Stacy Adams - Tallero Lace-Up. Color Black/Gray. Low Stock. On sale for $85.33. MSRP $115.00. 26% off. 4.6 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: Black/Gray
Price: $85.33MSRP: $115

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

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

PUMA - Royale. Color Puma White/Deep Navy/Team Light Blue. $159.99.

PUMA Royale

PUMA Royale

Brand Name: PUMA
Product Name: Royale
Gender: Men's
Color: Puma White/Deep Navy/Team Light Blue
Price: $159.99

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

Frye - Tyler Penny. Color Bronze. Low Stock. On sale for $116.05. MSRP $258.00. 55% off. 3.1 out of 5 stars

Low Stock

Frye Tyler Penny

Frye Tyler Penny

Brand Name: Frye
Product Name: Tyler Penny
Gender: Men's
Color: Bronze
Price: $116.05MSRP: $258

Magnanni - Shaw. Color Rocia Taupe Suede. On sale for $396.00. MSRP $495.00. 20% off.

Magnanni Shaw

Magnanni Shaw

Brand Name: Magnanni
Product Name: Shaw
Gender: Men's
Color: Rocia Taupe Suede
Price: $396MSRP: $495

Marc Joseph New York - Spring Street. Color Ice Basket Napa. On sale for $105.00. MSRP $175.00. 40% off.

Marc Joseph New York Spring Street

Marc Joseph New York Spring Street

Brand Name: Marc Joseph New York
Product Name: Spring Street
Gender: Men's
Color: Ice Basket Napa
Price: $105MSRP: $175

TOMS - Travel Lite Forrest. Color Tan. On sale for $78.00. MSRP $130.00. 40% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Tan
Price: $78MSRP: $130

TOMS - Travel Lite Forrest. Color Brown. On sale for $97.50. MSRP $130.00. 25% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $97.50MSRP: $130

Gordon Rush - Austin. Color Espresso. Low Stock. $145.75. 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: $145.75

Wolf & Shepherd - Supercrossover. Color Navy. On sale for $250.75. MSRP $295.00. 15% off.

Wolf & Shepherd Supercrossover

Wolf & Shepherd Supercrossover

Brand Name: Wolf & Shepherd
Product Name: Supercrossover
Gender: Men's
Color: Navy
Price: $250.75MSRP: $295

Born - Cambridge. Color Black. On sale for $79.95. MSRP $135.00. 41% off.

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Black
Price: $79.95MSRP: $135

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

Born Cambridge

Born Cambridge

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

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 - 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 $88.58. 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: $88.58MSRP: $110

Cole Haan - Grand Crosscourt Modern Runner. Color Pavement/Biscuit/Storm Cloud. On sale for $89.07. 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: Pavement/Biscuit/Storm Cloud
Price: $89.07MSRP: $110

Magnanni - Jonas. Color Taupe. Low Stock. On sale for $367.50. MSRP $525.00. 30% off.

Low Stock

Magnanni Jonas

Magnanni Jonas

Brand Name: Magnanni
Product Name: Jonas
Gender: Men's
Color: Taupe
Price: $367.50MSRP: $525

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

Cole Haan - American Classics Montrose Plain Toe Ox. Color Navy Blazer Nubuck/Angora. On sale for $161.50. MSRP $190.00. 15% 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: $161.50MSRP: $190

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 - 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 $153.00. MSRP $170.00. 10% 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: $153MSRP: $170

Johnston & Murphy - Taylor Penny. Color Denim. Low Stock. On sale for $199.99. MSRP $298.00. 33% 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: $199.99MSRP: $298

Frye - Astor Low Lace Court. Color Bluestone. Low Stock. On sale for $142.20. MSRP $158.00. 10% off. 5.0 out of 5 stars

Low Stock

Frye Astor Low Lace Court

Frye Astor Low Lace Court

Brand Name: Frye
Product Name: Astor Low Lace Court
Gender: Men's
Color: Bluestone
Price: $142.20MSRP: $158

Frye - Connor Venetian. Color Driftwood. On sale for $79.00. MSRP $158.00. 50% 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: $79MSRP: $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

Cole Haan - Pinch Weekender Venetians. Color China Blue Suede/Ivory. On sale for $102.48. MSRP $130.00. 21% 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: $102.48MSRP: $130

Cole Haan - American Classics Montrose Plain Toe Ox. Color Light Sesame Suede/Birch Beige/Ivory. On sale for $171.00. MSRP $190.00. 10% 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: Light Sesame Suede/Birch Beige/Ivory
Price: $171MSRP: $190

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