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Boots on Sale $50 & Under

Shop Boots Deals

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Size 8.5 Medium Size Leather On Sale Products

437 items found

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Sperry - Ao 3 Lug. Color Other Brown. On sale for $114.75. MSRP $135.00. 15% off.

Sperry Ao 3 Lug

Sperry Ao 3 Lug

Brand Name: Sperry
Product Name: Ao 3 Lug
Gender: Men's
Color: Other Brown
Price: $114.75MSRP: $135

Sperry - Tour Mid Moc. Color Dark Brown. On sale for $126.00. MSRP $140.00. 10% off.

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Dark Brown
Price: $126MSRP: $140

Nunn Bush - Otto EZ Moccasin Toe Slip-On Easy On Loafer. Color Tan. Low Stock. On sale for $68.26. MSRP $90.00. 24% off. 3.5 out of 5 stars

Low Stock

Nunn Bush Otto EZ Moccasin Toe Slip-On Easy On Loafer

Nunn Bush Otto EZ Moccasin Toe Slip-On Easy On Loafer

Brand Name: Nunn Bush
Product Name: Otto EZ Moccasin Toe Slip-On Easy On Loafer
Gender: Men's
Color: Tan
Price: $68.26MSRP: $90

ECCO - Byway 2.0 Sneaker. Color Camel. Low Stock. On sale for $129.13. MSRP $184.95. 30% off.

Low Stock

ECCO Byway 2.0 Sneaker

ECCO Byway 2.0 Sneaker

Brand Name: ECCO
Product Name: Byway 2.0 Sneaker
Gender: Men's
Color: Camel
Price: $129.13MSRP: $184.95

Propet - Veymont. Color Grey/Blue. On sale for $128.00. MSRP $169.95. 25% off. 3.4 out of 5 stars

Propet Veymont

Propet Veymont

Brand Name: Propet
Product Name: Veymont
Gender: Men's
Color: Grey/Blue
Price: $128MSRP: $169.95

Propet - Vercors. Color Grey/Blue. Low Stock. On sale for $77.00. MSRP $144.95. 47% off. 3.4 out of 5 stars

Low Stock

Propet Vercors

Propet Vercors

Brand Name: Propet
Product Name: Vercors
Gender: Men's
Color: Grey/Blue
Price: $77MSRP: $144.95

Cole Haan - Grand Atlantic Sneaker. Color Marine Blue/British Tan. On sale for $84.00. MSRP $120.00. 30% off. 4.4 out of 5 stars

Cole Haan Grand Atlantic Sneaker

Cole Haan Grand Atlantic Sneaker

Brand Name: Cole Haan
Product Name: Grand Atlantic Sneaker
Gender: Men's
Color: Marine Blue/British Tan
Price: $84MSRP: $120

ECCO - Soft 60 Slip-On Sneaker. Color Black. Low Stock. On sale for $157.50. MSRP $175.00. 10% off.

Low Stock

ECCO Soft 60 Slip-On Sneaker

ECCO Soft 60 Slip-On Sneaker

Brand Name: ECCO
Product Name: Soft 60 Slip-On Sneaker
Gender: Men's
Color: Black
Price: $157.50MSRP: $175

ECCO - Gruuv Studio Wingtip Sneaker. Color Cocoa Brown/Mocha. Low Stock. On sale for $154.53. MSRP $194.95. 21% off. 4.0 out of 5 stars

Low Stock

ECCO Gruuv Studio Wingtip Sneaker

ECCO Gruuv Studio Wingtip Sneaker

Brand Name: ECCO
Product Name: Gruuv Studio Wingtip Sneaker
Gender: Men's
Color: Cocoa Brown/Mocha
Price: $154.53MSRP: $194.95

ECCO - Gruuv Studio Wingtip Sneaker. Color Black/Black. Low Stock. On sale for $149.33. MSRP $194.95. 23% off. 4.0 out of 5 stars

Low Stock

ECCO Gruuv Studio Wingtip Sneaker

ECCO Gruuv Studio Wingtip Sneaker

Brand Name: ECCO
Product Name: Gruuv Studio Wingtip Sneaker
Gender: Men's
Color: Black/Black
Price: $149.33MSRP: $194.95

Eastland 1955 Edition - Scarborough. Color Beige. Low Stock. On sale for $50.00. MSRP $125.00. 60% off. 5.0 out of 5 stars

Low Stock

Eastland 1955 Edition Scarborough

Eastland 1955 Edition Scarborough

Brand Name: Eastland 1955 Edition
Product Name: Scarborough
Gender: Men's
Color: Beige
Price: $50MSRP: $125

Eastland 1955 Edition - Baldwin. Color Black. Low Stock. On sale for $62.50. MSRP $125.00. 50% off. 3.0 out of 5 stars

Low Stock

Eastland 1955 Edition Baldwin

Eastland 1955 Edition Baldwin

Brand Name: Eastland 1955 Edition
Product Name: Baldwin
Gender: Men's
Color: Black
Price: $62.50MSRP: $125

Cole Haan - Grand Crosscourt 20.4.7 Ls Sneakers. Color Navy Blazer/British Tan/Ivory. On sale for $109.97. MSRP $130.00. 15% off.

Cole Haan Grand Crosscourt 20.4.7 Ls Sneakers

Cole Haan Grand Crosscourt 20.4.7 Ls Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt 20.4.7 Ls Sneakers
Gender: Men's
Color: Navy Blazer/British Tan/Ivory
Price: $109.97MSRP: $130

Johnston & Murphy - Kinnon T-Toe. Color Navy Suede/White Full Grain. On sale for $131.75. MSRP $155.00. 15% off.

Johnston & Murphy Kinnon T-Toe

Johnston & Murphy Kinnon T-Toe

Brand Name: Johnston & Murphy
Product Name: Kinnon T-Toe
Gender: Men's
Color: Navy Suede/White Full Grain
Price: $131.75MSRP: $155

Johnston & Murphy - Upton Perfed Plain Toe. Color Taupe. On sale for $73.68. MSRP $149.00. 51% off. 5.0 out of 5 stars

Johnston & Murphy Upton Perfed Plain Toe

Johnston & Murphy Upton Perfed Plain Toe

Brand Name: Johnston & Murphy
Product Name: Upton Perfed Plain Toe
Gender: Men's
Color: Taupe
Price: $73.68MSRP: $149

Johnston & Murphy - Gibbons Wingtip. Color Black Full Grain. On sale for $116.10. MSRP $129.00. 10% off. 3.8 out of 5 stars

Johnston & Murphy Gibbons Wingtip

Johnston & Murphy Gibbons Wingtip

Brand Name: Johnston & Murphy
Product Name: Gibbons Wingtip
Gender: Men's
Color: Black Full Grain
Price: $116.10MSRP: $129

Johnston & Murphy - Kinnon T-Toe. Color Sand Suede/White Full Grain. On sale for $116.25. MSRP $155.00. 25% off.

Johnston & Murphy Kinnon T-Toe

Johnston & Murphy Kinnon T-Toe

Brand Name: Johnston & Murphy
Product Name: Kinnon T-Toe
Gender: Men's
Color: Sand Suede/White Full Grain
Price: $116.25MSRP: $155

Johnston & Murphy - Monaco 2-Eye Boat Shoe. Color Tan Multi Sheepskin. Low Stock. On sale for $134.10. MSRP $149.00. 10% off.

Low Stock

Johnston & Murphy Monaco 2-Eye Boat Shoe

Johnston & Murphy Monaco 2-Eye Boat Shoe

Brand Name: Johnston & Murphy
Product Name: Monaco 2-Eye Boat Shoe
Gender: Men's
Color: Tan Multi Sheepskin
Price: $134.10MSRP: $149

Cole Haan - American Classics Montrose Plain Toe Ox. Color Navy Blazer Nubuck/Angora. On sale for $142.50. 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: $142.50MSRP: $190

Cole Haan - Originalgrand Energyweave Venetian Loafers. Color Ironstone Nubuck/Paloma/Paloma. On sale for $120.00. MSRP $160.00. 25% off. 5.0 out of 5 stars

Cole Haan Originalgrand Energyweave Venetian Loafers

Cole Haan Originalgrand Energyweave Venetian Loafers

Brand Name: Cole Haan
Product Name: Originalgrand Energyweave Venetian Loafers
Gender: Men's
Color: Ironstone Nubuck/Paloma/Paloma
Price: $120MSRP: $160

Cole Haan - Davies Grand Penny Driving Loafers. Color China Blue Suede/Gum. Low Stock. On sale for $100.50. MSRP $150.00. 33% off. 5.0 out of 5 stars

Low Stock

Cole Haan Davies Grand Penny Driving Loafers

Cole Haan Davies Grand Penny Driving Loafers

Brand Name: Cole Haan
Product Name: Davies Grand Penny Driving Loafers
Gender: Men's
Color: China Blue Suede/Gum
Price: $100.50MSRP: $150

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 - Originalgrand Energyweave Venetian Loafers. Color Navy Blazer/Paloma/Gum. On sale for $120.00. MSRP $160.00. 25% off. 5.0 out of 5 stars

Cole Haan Originalgrand Energyweave Venetian Loafers

Cole Haan Originalgrand Energyweave Venetian Loafers

Brand Name: Cole Haan
Product Name: Originalgrand Energyweave Venetian Loafers
Gender: Men's
Color: Navy Blazer/Paloma/Gum
Price: $120MSRP: $160

Born - Laken. Color Dark Brown (Castagno). Low Stock. On sale for $65.00. MSRP $100.00. 35% off.

Low Stock

Born Laken

Born Laken

Brand Name: Born
Product Name: Laken
Gender: Men's
Color: Dark Brown (Castagno)
Price: $65MSRP: $100

Johnston & Murphy - Jenson Chelsea Boot. Color Black Tumbled Calfskin. Low Stock. On sale for $123.00. MSRP $325.00. 62% off. 5.0 out of 5 stars

Low Stock

Johnston & Murphy Jenson Chelsea Boot

Johnston & Murphy Jenson Chelsea Boot

Brand Name: Johnston & Murphy
Product Name: Jenson Chelsea Boot
Gender: Men's
Color: Black Tumbled Calfskin
Price: $123MSRP: $325

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $179.97. MSRP $285.00. 37% off.

Low Stock

Johnston & Murphy Bolivar Plain Toe Boots

Johnston & Murphy Bolivar Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Bolivar Plain Toe Boots
Gender: Men's
Color: Snuff Italian Suede
Price: $179.97MSRP: $285

etnies - Camber Mid Michelin. Color Black. Low Stock. On sale for $136.00. MSRP $160.00. 15% off. 4.0 out of 5 stars

Low Stock

etnies Camber Mid Michelin

etnies Camber Mid Michelin

Brand Name: etnies
Product Name: Camber Mid Michelin
Gender: Men's
Color: Black
Price: $136MSRP: $160

Johnston & Murphy - Richland Monk Strap. Color Black Full Grain. On sale for $140.25. MSRP $165.00. 15% off. 1.0 out of 5 stars

Johnston & Murphy Richland Monk Strap

Johnston & Murphy Richland Monk Strap

Brand Name: Johnston & Murphy
Product Name: Richland Monk Strap
Gender: Men's
Color: Black Full Grain
Price: $140.25MSRP: $165

Johnston & Murphy - Sullivan Cap Toe. Color Espresso Italian Calfskin. On sale for $179.10. MSRP $199.00. 10% off.

Johnston & Murphy Sullivan Cap Toe

Johnston & Murphy Sullivan Cap Toe

Brand Name: Johnston & Murphy
Product Name: Sullivan Cap Toe
Gender: Men's
Color: Espresso Italian Calfskin
Price: $179.10MSRP: $199

Josef Seibel - Finley 01. Color Black/Kombi Oiled Full Grain/Kombi. On sale for $60.00. MSRP $150.00. 60% off. 1.5 out of 5 stars

Josef Seibel Finley 01

Josef Seibel Finley 01

Brand Name: Josef Seibel
Product Name: Finley 01
Gender: Men's
Color: Black/Kombi Oiled Full Grain/Kombi
Price: $60MSRP: $150

Josef Seibel - Finley 02. Color Black Full Grain/Kombi. On sale for $60.00. MSRP $150.00. 60% off.

Josef Seibel Finley 02

Josef Seibel Finley 02

Brand Name: Josef Seibel
Product Name: Finley 02
Gender: Men's
Color: Black Full Grain/Kombi
Price: $60MSRP: $150

SKECHERS - Go Walk Outdoor Hands Free Slip-Ins. Color Charcoal. On sale for $71.88. MSRP $100.00. 28% off. 4.4 out of 5 stars

SKECHERS Go Walk Outdoor Hands Free Slip-Ins

SKECHERS Go Walk Outdoor Hands Free Slip-Ins

Brand Name: SKECHERS
Product Name: Go Walk Outdoor Hands Free Slip-Ins
Gender: Men's
Color: Charcoal
Price: $71.88MSRP: $100

Vans - MTE Ultrarange 2.0 RW. Color Bungee Cord. On sale for $85.00. MSRP $100.00. 15% off. 3.7 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: $85MSRP: $100

Sperry - Newton Boots. Color Taupe. On sale for $148.50. MSRP $165.00. 10% off. 5.0 out of 5 stars

Sperry Newton Boots

Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $148.50MSRP: $165

Sperry - Stringer. Color Tan. On sale for $117.00. MSRP $130.00. 10% off.

Sperry Stringer

Sperry Stringer

Brand Name: Sperry
Product Name: Stringer
Gender: Men's
Color: Tan
Price: $117MSRP: $130

Sperry - Tour Mid Moc. Color Tan. Low Stock. On sale for $126.00. MSRP $140.00. 10% off.

Low Stock

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Tan
Price: $126MSRP: $140

Sperry - Ao 3 Lug. Color Tan. On sale for $108.00. MSRP $135.00. 20% off.

Sperry Ao 3 Lug

Sperry Ao 3 Lug

Brand Name: Sperry
Product Name: Ao 3 Lug
Gender: Men's
Color: Tan
Price: $108MSRP: $135

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