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Boots on Sale $50 & Under

Shop Boots Deals

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Size 8 Leather Comfort Products

35 items found

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Red Wing Heritage - Iron Ranger Traction Tred. Color Oro Legacy. On sale for $244.99. MSRP $349.99. 30% off.

Red Wing Heritage Iron Ranger Traction Tred

Red Wing Heritage Iron Ranger Traction Tred

Brand Name: Red Wing Heritage
Product Name: Iron Ranger Traction Tred
Gender: Men's
Color: Oro Legacy
Price: $244.99MSRP: $349.99

Cole Haan - Ledley Grand Cap Toe Oxfords. Color Madeira/Dark Natural. On sale for $279.00. MSRP $310.00. 10% off.

Cole Haan Ledley Grand Cap Toe Oxfords

Cole Haan Ledley Grand Cap Toe Oxfords

Brand Name: Cole Haan
Product Name: Ledley Grand Cap Toe Oxfords
Gender: Men's
Color: Madeira/Dark Natural
Price: $279MSRP: $310

Frye - Barrett Lace Up. Color Black. On sale for $223.20. MSRP $248.00. 10% off. 5.0 out of 5 stars

Frye Barrett Lace Up

Frye Barrett Lace Up

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Black
Price: $223.20MSRP: $248

ECCO - Biom C4 Vented GORE-TEX® Waterproof Golf Shoe. Color Concrete/Baygreen. Low Stock. On sale for $203.10. MSRP $249.00. 18% off. 4.4 out of 5 stars

Low Stock

ECCO Biom C4 Vented GORE-TEX® Waterproof Golf Shoe

ECCO Biom C4 Vented GORE-TEX® Waterproof Golf Shoe

Brand Name: ECCO
Product Name: Biom C4 Vented GORE-TEX® Waterproof Golf Shoe
Gender: Men's
Color: Concrete/Baygreen
Price: $203.10MSRP: $249

Martin Dingman - Huntley Chelsea Boot. Color Walnut. Low Stock. On sale for $315.00. MSRP $350.00. 10% off.

Low Stock

Martin Dingman Huntley Chelsea Boot

Martin Dingman Huntley Chelsea Boot

Brand Name: Martin Dingman
Product Name: Huntley Chelsea Boot
Gender: Men's
Color: Walnut
Price: $315MSRP: $350

Cole Haan - Roundhill Grand Chelsea Boots. Color Black/Black Waterproof. On sale for $234.00. MSRP $260.00. 10% off. 5.0 out of 5 stars

Cole Haan Roundhill Grand Chelsea Boots

Cole Haan Roundhill Grand Chelsea Boots

Brand Name: Cole Haan
Product Name: Roundhill Grand Chelsea Boots
Gender: Men's
Color: Black/Black Waterproof
Price: $234MSRP: $260

Red Wing Heritage - Iron Ranger Traction Tred. Color Amber Harness. Low Stock. On sale for $244.99. MSRP $349.99. 30% off.

Low Stock

Red Wing Heritage Iron Ranger Traction Tred

Red Wing Heritage Iron Ranger Traction Tred

Brand Name: Red Wing Heritage
Product Name: Iron Ranger Traction Tred
Gender: Men's
Color: Amber Harness
Price: $244.99MSRP: $349.99

Magnanni - Costa Slip Perf. Color White. Low Stock. On sale for $337.50. MSRP $450.00. 25% off.

Low Stock

Magnanni Costa Slip Perf

Magnanni Costa Slip Perf

Brand Name: Magnanni
Product Name: Costa Slip Perf
Gender: Men's
Color: White
Price: $337.50MSRP: $450

Magnanni - Eu Bravo. Color Tierra. Low Stock. On sale for $409.50. MSRP $455.00. 10% off.

Low Stock

Magnanni Eu Bravo

Magnanni Eu Bravo

Brand Name: Magnanni
Product Name: Eu Bravo
Gender: Men's
Color: Tierra
Price: $409.50MSRP: $455

Magnanni - Macsen. Color Black. Low Stock. On sale for $403.75. MSRP $475.00. 15% off.

Low Stock

Magnanni Macsen

Magnanni Macsen

Brand Name: Magnanni
Product Name: Macsen
Gender: Men's
Color: Black
Price: $403.75MSRP: $475

Magnanni - Leone. Color Tabaco. Low Stock. On sale for $427.50. MSRP $475.00. 10% off.

Low Stock

Magnanni Leone

Magnanni Leone

Brand Name: Magnanni
Product Name: Leone
Gender: Men's
Color: Tabaco
Price: $427.50MSRP: $475

Johnston & Murphy - Jenson Plain Toe. Color Gray Italian Suede. On sale for $213.75. MSRP $285.00. 25% off. 4.0 out of 5 stars

Johnston & Murphy Jenson Plain Toe

Johnston & Murphy Jenson Plain Toe

Brand Name: Johnston & Murphy
Product Name: Jenson Plain Toe
Gender: Men's
Color: Gray Italian Suede
Price: $213.75MSRP: $285

Samuel Hubbard - DressFast. Color Black. $295.00. 4.4 out of 5 stars

Samuel Hubbard DressFast

Samuel Hubbard DressFast

Brand Name: Samuel Hubbard
Product Name: DressFast
Gender: Men's
Color: Black
Price: $295

Samuel Hubbard - Frequent Traveler Loafer. Color Black. $285.00. 4.5 out of 5 stars

Samuel Hubbard Frequent Traveler Loafer

Samuel Hubbard Frequent Traveler Loafer

Brand Name: Samuel Hubbard
Product Name: Frequent Traveler Loafer
Gender: Men's
Color: Black
Price: $285

Johnston & Murphy - Jenson Plain Toe. Color Tan European Calfskin. Low Stock. On sale for $247.50. MSRP $275.00. 10% off. 4.0 out of 5 stars

Low Stock

Johnston & Murphy Jenson Plain Toe

Johnston & Murphy Jenson Plain Toe

Brand Name: Johnston & Murphy
Product Name: Jenson Plain Toe
Gender: Men's
Color: Tan European Calfskin
Price: $247.50MSRP: $275

Samuel Hubbard - DressFast. Color Cognac Leather. $295.00. 4.4 out of 5 stars

Samuel Hubbard DressFast

Samuel Hubbard DressFast

Brand Name: Samuel Hubbard
Product Name: DressFast
Gender: Men's
Color: Cognac Leather
Price: $295

Magnanni - Daren. Color Navy. Low Stock. On sale for $393.75. MSRP $525.00. 25% off.

Low Stock

Magnanni Daren

Magnanni Daren

Brand Name: Magnanni
Product Name: Daren
Gender: Men's
Color: Navy
Price: $393.75MSRP: $525

Magnanni - Lawford Flx. Color Taupe Suede. Low Stock. On sale for $332.50. MSRP $475.00. 30% off. 5.0 out of 5 stars

Low Stock

Magnanni Lawford Flx

Magnanni Lawford Flx

Brand Name: Magnanni
Product Name: Lawford Flx
Gender: Men's
Color: Taupe Suede
Price: $332.50MSRP: $475

Peter Millar - Tempest Boots. Color Beach. Low Stock. On sale for $265.50. MSRP $295.00. 10% off.

Low Stock

Peter Millar Tempest Boots

Peter Millar Tempest Boots

Brand Name: Peter Millar
Product Name: Tempest Boots
Gender: Men's
Color: Beach
Price: $265.50MSRP: $295

Johnston & Murphy - Jenson Longwing. Color Black. On sale for $236.00. MSRP $295.00. 20% off. 4.1 out of 5 stars

Johnston & Murphy Jenson Longwing

Johnston & Murphy Jenson Longwing

Brand Name: Johnston & Murphy
Product Name: Jenson Longwing
Gender: Men's
Color: Black
Price: $236MSRP: $295

Cole Haan - Berkshire Chelsea Boots. Color Lava Suede/Dark. Low Stock. On sale for $229.71. MSRP $250.00. 8% off. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Lava Suede/Dark
Price: $229.71MSRP: $250

Magnanni - Orion Cap. Color Brown. Low Stock. On sale for $239.97. MSRP $475.00. 49% off.

Low Stock

Magnanni Orion Cap

Magnanni Orion Cap

Brand Name: Magnanni
Product Name: Orion Cap
Gender: Men's
Color: Brown
Price: $239.97MSRP: $475

Johnston & Murphy - Jared Lace to Toe. Color White. On sale for $206.50. MSRP $295.00. 30% off. 2.0 out of 5 stars

Johnston & Murphy Jared Lace to Toe

Johnston & Murphy Jared Lace to Toe

Brand Name: Johnston & Murphy
Product Name: Jared Lace to Toe
Gender: Men's
Color: White
Price: $206.50MSRP: $295

Johnston & Murphy - Bolivar Venetian. Color Snuff. On sale for $206.25. MSRP $275.00. 25% off. 4.6 out of 5 stars

Johnston & Murphy Bolivar Venetian

Johnston & Murphy Bolivar Venetian

Brand Name: Johnston & Murphy
Product Name: Bolivar Venetian
Gender: Men's
Color: Snuff
Price: $206.25MSRP: $275

Vince - Sonoma Slip-On Loafer. Color Coriander Brown Suede. Low Stock. On sale for $206.08. MSRP $225.00. 8% off.

Low Stock

Vince Sonoma Slip-On Loafer

Vince Sonoma Slip-On Loafer

Brand Name: Vince
Product Name: Sonoma Slip-On Loafer
Gender: Men's
Color: Coriander Brown Suede
Price: $206.08MSRP: $225

Wolf & Shepherd - Marathon Trainer. Color Navy. $225.00.

Wolf & Shepherd Marathon Trainer

Wolf & Shepherd Marathon Trainer

Brand Name: Wolf & Shepherd
Product Name: Marathon Trainer
Gender: Men's
Color: Navy
Price: $225

Wolf & Shepherd - Baller Sport. Color Black. Low Stock. $225.00. 5.0 out of 5 stars

Low Stock

Wolf & Shepherd Baller Sport

Wolf & Shepherd Baller Sport

Brand Name: Wolf & Shepherd
Product Name: Baller Sport
Gender: Men's
Color: Black
Price: $225

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

KEEN Utility - Camden 8" Waterproof 600G (Comp Toe). Color Leather Brown/Black. $235.00. 3.9 out of 5 stars

KEEN Utility Camden 8" Waterproof 600G (Comp Toe)

KEEN Utility Camden 8" Waterproof 600G (Comp Toe)

Brand Name: KEEN Utility
Product Name: Camden 8" Waterproof 600G (Comp Toe)
Gender: Men's
Color: Leather Brown/Black
Price: $235

Samuel Hubbard - Sunset Sneakers 2.0. Color White Leather. $210.00.

Samuel Hubbard Sunset Sneakers 2.0

Samuel Hubbard Sunset Sneakers 2.0

Brand Name: Samuel Hubbard
Product Name: Sunset Sneakers 2.0
Gender: Men's
Color: White Leather
Price: $210

Samuel Hubbard - Sunset Sneakers 2.0. Color Black Leather. $210.00.

Samuel Hubbard Sunset Sneakers 2.0

Samuel Hubbard Sunset Sneakers 2.0

Brand Name: Samuel Hubbard
Product Name: Sunset Sneakers 2.0
Gender: Men's
Color: Black Leather
Price: $210

Cole Haan - Original Grand 2.0 Oxford. Color Raven Nubuck/Midnight Moon. On sale for $216.00. MSRP $240.00. 10% off. 3.7 out of 5 stars

Cole Haan Original Grand 2.0 Oxford

Cole Haan Original Grand 2.0 Oxford

Brand Name: Cole Haan
Product Name: Original Grand 2.0 Oxford
Gender: Men's
Color: Raven Nubuck/Midnight Moon
Price: $216MSRP: $240

Cole Haan - Original Grand 2.0 Oxford. Color Brown Nubuck/Water Resistant. On sale for $216.00. MSRP $240.00. 10% off. 3.7 out of 5 stars

Cole Haan Original Grand 2.0 Oxford

Cole Haan Original Grand 2.0 Oxford

Brand Name: Cole Haan
Product Name: Original Grand 2.0 Oxford
Gender: Men's
Color: Brown Nubuck/Water Resistant
Price: $216MSRP: $240

ECCO - Oslo Penny Loafers. Color Black. On sale for $224.95. MSRP $249.95. 10% off. 5.0 out of 5 stars

ECCO Oslo Penny Loafers

ECCO Oslo Penny Loafers

Brand Name: ECCO
Product Name: Oslo Penny Loafers
Gender: Men's
Color: Black
Price: $224.95MSRP: $249.95

Mephisto - Hasko. Color Hazelnut. On sale for $289.00. MSRP $349.00. 17% off.

Mephisto Hasko

Mephisto Hasko

Brand Name: Mephisto
Product Name: Hasko
Gender: Men's
Color: Hazelnut
Price: $289MSRP: $349