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Boots on Sale $50 & Under

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Size 8.5 Arch Support Comfort On Sale Products

38 items found

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Dr. Scholl's - Jake Oxford. Color Brown Smooth. On sale for $57.88. MSRP $100.00. 42% off.

Dr. Scholl's Jake Oxford

Dr. Scholl's Jake Oxford

Brand Name: Dr. Scholl's
Product Name: Jake Oxford
Gender: Men's
Color: Brown Smooth
Price: $57.88MSRP: $100.00

Eastland 1955 Edition - Hugo. Color Black. On sale for $60.00. MSRP $100.00. 40% off.

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Black
Price: $60.00MSRP: $100.00

SKECHERS - Arch Fit 2.0 Look Ahead Hands Free Slip-In. Color Black/Black. On sale for $85.06. MSRP $105.00. 19% off. 4.2 out of 5 stars

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

Brand Name: SKECHERS
Product Name: Arch Fit 2.0 Look Ahead Hands Free Slip-In
Gender: Men's
Color: Black/Black
Price: $85.06MSRP: $105.00

SKECHERS - Craster Lanigan Hands Free Slip-Ins. Color Black. On sale for $83.44. MSRP $96.00. 13% off. 4.2 out of 5 stars

SKECHERS Craster Lanigan Hands Free Slip-Ins

SKECHERS Craster Lanigan Hands Free Slip-Ins

Brand Name: SKECHERS
Product Name: Craster Lanigan Hands Free Slip-Ins
Gender: Men's
Color: Black
Price: $83.44MSRP: $96.00

Dr. Scholl's - Jake Oxford. Color Black Smooth. On sale for $58.05. MSRP $100.00. 42% off.

Dr. Scholl's Jake Oxford

Dr. Scholl's Jake Oxford

Brand Name: Dr. Scholl's
Product Name: Jake Oxford
Gender: Men's
Color: Black Smooth
Price: $58.05MSRP: $100.00

Marc Joseph New York - Morris Street. Color Whiskey Napa. Low Stock. On sale for $52.50. MSRP $175.00. 70% off.

Low Stock

Marc Joseph New York Morris Street

Marc Joseph New York Morris Street

Brand Name: Marc Joseph New York
Product Name: Morris Street
Gender: Men's
Color: Whiskey Napa
Price: $52.50MSRP: $175.00

Dr. Scholl's - Sync Knit Lace Up Oxford. Color Grey Knit. On sale for $61.00. MSRP $100.00. 39% off. 3.3 out of 5 stars

Dr. Scholl's Sync Knit Lace Up Oxford

Dr. Scholl's Sync Knit Lace Up Oxford

Brand Name: Dr. Scholl's
Product Name: Sync Knit Lace Up Oxford
Gender: Men's
Color: Grey Knit
Price: $61.00MSRP: $100.00

SKECHERS - Arch Fit 2.0 Look Ahead Hands Free Slip-In. Color Navy. On sale for $97.19. MSRP $105.00. 7% off. 4.2 out of 5 stars

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

Brand Name: SKECHERS
Product Name: Arch Fit 2.0 Look Ahead Hands Free Slip-In
Gender: Men's
Color: Navy
Price: $97.19MSRP: $105.00

Stacy Adams - Spencer Penny Slip-On. Color Navy. On sale for $70.38. MSRP $130.00. 46% off. 4.8 out of 5 stars

Stacy Adams Spencer Penny Slip-On

Stacy Adams Spencer Penny Slip-On

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Navy
Price: $70.38MSRP: $130.00

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Black Suede. On sale for $94.52. MSRP $115.00. 18% off. 4.7 out of 5 stars

Stacy Adams Ravelle Moc Toe Bit Slip-On

Stacy Adams Ravelle Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Ravelle Moc Toe Bit Slip-On
Gender: Men's
Color: Black Suede
Price: $94.52MSRP: $115.00

Stacy Adams - Madsen Moc Toe Bit Slip-On. Color Black. Low Stock. On sale for $90.00. MSRP $130.00. 31% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Madsen Moc Toe Bit Slip-On

Stacy Adams Madsen Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Madsen Moc Toe Bit Slip-On
Gender: Men's
Color: Black
Price: $90.00MSRP: $130.00

Stacy Adams - Spencer Penny Slip-On. Color Burgundy. On sale for $84.50. MSRP $130.00. 35% off. 4.8 out of 5 stars

Stacy Adams Spencer Penny Slip-On

Stacy Adams Spencer Penny Slip-On

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Burgundy
Price: $84.50MSRP: $130.00

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Green Suede. On sale for $97.07. MSRP $115.00. 16% off. 4.7 out of 5 stars

Stacy Adams Ravelle Moc Toe Bit Slip-On

Stacy Adams Ravelle Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Ravelle Moc Toe Bit Slip-On
Gender: Men's
Color: Green Suede
Price: $97.07MSRP: $115.00

SKECHERS - Arch Fit 2.0 Look Ahead Hands Free Slip-In. Color White/Black. On sale for $90.97. MSRP $105.00. 13% off. 4.2 out of 5 stars

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

SKECHERS Arch Fit 2.0 Look Ahead Hands Free Slip-In

Brand Name: SKECHERS
Product Name: Arch Fit 2.0 Look Ahead Hands Free Slip-In
Gender: Men's
Color: White/Black
Price: $90.97MSRP: $105.00

Clarks - Whiddon Mid. Color Mahogany Leather. Low Stock. On sale for $86.53. MSRP $110.00. 21% off. 3.4 out of 5 stars

Low Stock

Clarks Whiddon Mid

Clarks Whiddon Mid

Brand Name: Clarks
Product Name: Whiddon Mid
Gender: Men's
Color: Mahogany Leather
Price: $86.53MSRP: $110.00

Dr. Scholl's - Jake Retro. Color White Grey Fabric. Low Stock. On sale for $94.50. MSRP $105.00. 10% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Jake Retro

Dr. Scholl's Jake Retro

Brand Name: Dr. Scholl's
Product Name: Jake Retro
Gender: Men's
Color: White Grey Fabric
Price: $94.50MSRP: $105.00

Stacy Adams - Remy Perfed Slip-On. Color Navy. Low Stock. On sale for $63.71. MSRP $84.95. 25% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Remy Perfed Slip-On

Stacy Adams Remy Perfed Slip-On

Brand Name: Stacy Adams
Product Name: Remy Perfed Slip-On
Gender: Men's
Color: Navy
Price: $63.71MSRP: $84.95

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $79.51. MSRP $104.95. 24% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Gill Saddle Slip-On Loafer

Stacy Adams Gill Saddle Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Gill Saddle Slip-On Loafer
Gender: Men's
Color: Mushroom Multi
Price: $79.51MSRP: $104.95

Stacy Adams - Tallero Lace-Up. Color Dark Blue Multi. On sale for $90.52. MSRP $115.00. 21% off. 4.2 out of 5 stars

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: $90.52MSRP: $115.00

Stacy Adams - Tallero Lace-Up. Color Tan Multi. On sale for $90.27. MSRP $115.00. 22% off. 4.2 out of 5 stars

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: $90.27MSRP: $115.00

Stacy Adams - Tallero Lace-Up. Color Burgundy Multi. On sale for $97.12. MSRP $115.00. 16% off. 4.2 out of 5 stars

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: $97.12MSRP: $115.00

Dr. Scholl's - Synergy Sneaker. Color White Grey. Low Stock. On sale for $94.50. MSRP $105.00. 10% off.

Low Stock

Dr. Scholl's Synergy Sneaker

Dr. Scholl's Synergy Sneaker

Brand Name: Dr. Scholl's
Product Name: Synergy Sneaker
Gender: Men's
Color: White Grey
Price: $94.50MSRP: $105.00

Stacy Adams - Kallum Cap Toe Oxford. Color Navy. Low Stock. On sale for $97.50. MSRP $130.00. 25% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Kallum Cap Toe Oxford

Stacy Adams Kallum Cap Toe Oxford

Brand Name: Stacy Adams
Product Name: Kallum Cap Toe Oxford
Gender: Men's
Color: Navy
Price: $97.50MSRP: $130.00

Eastland 1955 Edition - Hugo. Color Brown. On sale for $70.00. MSRP $100.00. 30% off.

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Brown
Price: $70.00MSRP: $100.00

SKECHERS - Drive 6 Relaxed Fit Spikeless Golf Shoe. Color Gray. On sale for $93.09. MSRP $115.00. 19% off. 5.0 out of 5 stars

SKECHERS Drive 6 Relaxed Fit Spikeless Golf Shoe

SKECHERS Drive 6 Relaxed Fit Spikeless Golf Shoe

Brand Name: SKECHERS
Product Name: Drive 6 Relaxed Fit Spikeless Golf Shoe
Gender: Men's
Color: Gray
Price: $93.09MSRP: $115.00

SKECHERS - Elite Vortex Rival ArchFit Golf Shoe. Color White/Navy. On sale for $99.92. MSRP $115.00. 13% off. 4.0 out of 5 stars

SKECHERS Elite Vortex Rival ArchFit Golf Shoe

SKECHERS Elite Vortex Rival ArchFit Golf Shoe

Brand Name: SKECHERS
Product Name: Elite Vortex Rival ArchFit Golf Shoe
Gender: Men's
Color: White/Navy
Price: $99.92MSRP: $115.00

Dr. Scholl's - Madison Men Oxford Derby. Color Light Tan Faux Leather. On sale for $61.20. MSRP $95.00. 36% off.

Dr. Scholl's Madison Men Oxford Derby

Dr. Scholl's Madison Men Oxford Derby

Brand Name: Dr. Scholl's
Product Name: Madison Men Oxford Derby
Gender: Men's
Color: Light Tan Faux Leather
Price: $61.20MSRP: $95.00

Stacy Adams - Martindale Chukka Boot. Color Bordeaux. Low Stock. On sale for $91.00. MSRP $130.00. 30% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Martindale Chukka Boot

Stacy Adams Martindale Chukka Boot

Brand Name: Stacy Adams
Product Name: Martindale Chukka Boot
Gender: Men's
Color: Bordeaux
Price: $91.00MSRP: $130.00

Stacy Adams - Feronte Bit Slip-On. Color Cognac. On sale for $96.59. MSRP $130.00. 26% off. 5.0 out of 5 stars

Stacy Adams Feronte Bit Slip-On

Stacy Adams Feronte Bit Slip-On

Brand Name: Stacy Adams
Product Name: Feronte Bit Slip-On
Gender: Men's
Color: Cognac
Price: $96.59MSRP: $130.00

Stacy Adams - Franz Tassel Slip-On. Color Cognac. Low Stock. On sale for $97.97. MSRP $130.00. 25% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Franz Tassel Slip-On

Stacy Adams Franz Tassel Slip-On

Brand Name: Stacy Adams
Product Name: Franz Tassel Slip-On
Gender: Men's
Color: Cognac
Price: $97.97MSRP: $130.00

Stacy Adams - Feronte Bit Slip-On. Color Black. On sale for $97.20. MSRP $130.00. 25% off. 5.0 out of 5 stars

Stacy Adams Feronte Bit Slip-On

Stacy Adams Feronte Bit Slip-On

Brand Name: Stacy Adams
Product Name: Feronte Bit Slip-On
Gender: Men's
Color: Black
Price: $97.20MSRP: $130.00

SKECHERS - Drive 6 Relaxed Fit Spikeless Golf Shoe. Color Black/White. On sale for $90.80. MSRP $115.00. 21% off. 5.0 out of 5 stars

SKECHERS Drive 6 Relaxed Fit Spikeless Golf Shoe

SKECHERS Drive 6 Relaxed Fit Spikeless Golf Shoe

Brand Name: SKECHERS
Product Name: Drive 6 Relaxed Fit Spikeless Golf Shoe
Gender: Men's
Color: Black/White
Price: $90.80MSRP: $115.00

Stacy Adams - Sync Lace-Up. Color Natural. On sale for $99.99. MSRP $125.00. 20% off. 4.3 out of 5 stars

Stacy Adams Sync Lace-Up

Stacy Adams Sync Lace-Up

Brand Name: Stacy Adams
Product Name: Sync Lace-Up
Gender: Men's
Color: Natural
Price: $99.99MSRP: $125.00

KEEN - Waimea TG. Color Cornstalk/Black. On sale for $63.75. MSRP $84.95. 25% off. 4.1 out of 5 stars

KEEN Waimea TG

KEEN Waimea TG

Brand Name: KEEN
Product Name: Waimea TG
Gender: Men's
Color: Cornstalk/Black
Price: $63.75MSRP: $84.95

Propet - Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe. Color Dark Grey. On sale for $96.74. MSRP $107.49. 10% off. 4.5 out of 5 stars

Propet Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe

Propet Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe

Brand Name: Propet
Product Name: Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe
Gender: Men's
Color: Dark Grey
Price: $96.74MSRP: $107.49

SKECHERS - Pro 6 SL. Color Off-White. On sale for $92.84. MSRP $129.99. 29% off. 4.1 out of 5 stars

SKECHERS Pro 6 SL

SKECHERS Pro 6 SL

Brand Name: SKECHERS
Product Name: Pro 6 SL
Gender: Men's
Color: Off-White
Price: $92.84MSRP: $129.99

SKECHERS - Pro 6 SL. Color Black/Grey. Low Stock. On sale for $90.99. MSRP $129.99. 30% off. 4.1 out of 5 stars

Low Stock

SKECHERS Pro 6 SL

SKECHERS Pro 6 SL

Brand Name: SKECHERS
Product Name: Pro 6 SL
Gender: Men's
Color: Black/Grey
Price: $90.99MSRP: $129.99

SKECHERS - Hands Free Slip-Ins Go Walk Arch Fit 2.0 - Simplicity 2. Color Charcoal/Orange. On sale for $94.50. MSRP $105.00. 10% off. 4.2 out of 5 stars

SKECHERS Hands Free Slip-Ins Go Walk Arch Fit 2.0 - Simplicity 2

SKECHERS Hands Free Slip-Ins Go Walk Arch Fit 2.0 - Simplicity 2

Brand Name: SKECHERS
Product Name: Hands Free Slip-Ins Go Walk Arch Fit 2.0 - Simplicity 2
Gender: Men's
Color: Charcoal/Orange
Price: $94.50MSRP: $105.00