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Boots on Sale $50 & Under

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Size 8.5 Arch Support Comfort On Sale Products

46 items found

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Nunn Bush - Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On. Color Black. On sale for $59.97. MSRP $100.00. 40% off. 1.5 out of 5 stars

Nunn Bush Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On

Nunn Bush Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On

Brand Name: Nunn Bush
Product Name: Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On
Gender: Men's
Color: Black
Price: $59.97MSRP: $100

Orthofeet - Leo. Color Black. On sale for $99.99. MSRP $145.00. 31% off. 3.0 out of 5 stars

Orthofeet Leo

Orthofeet Leo

Brand Name: Orthofeet
Product Name: Leo
Gender: Men's
Color: Black
Price: $99.99MSRP: $145

Deer Stags - Infinity. Color Brown. On sale for $44.97. MSRP $64.99. 31% off. 4.7 out of 5 stars

Deer Stags Infinity

Deer Stags Infinity

Brand Name: Deer Stags
Product Name: Infinity
Gender: Men's
Color: Brown
Price: $44.97MSRP: $64.99

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Black Suede. Low Stock. On sale for $34.50. MSRP $115.00. 70% off. 4.5 out of 5 stars

Low Stock

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: $34.50MSRP: $115

KEEN - Waimea TG. Color Cornstalk/Black. On sale for $63.18. MSRP $84.95. 26% 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: $63.18MSRP: $84.95

Dr. Scholl's - Feel Engaged. Color Black Leather. Low Stock. On sale for $97.50. MSRP $130.00. 25% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Feel Engaged

Dr. Scholl's Feel Engaged

Brand Name: Dr. Scholl's
Product Name: Feel Engaged
Gender: Men's
Color: Black Leather
Price: $97.50MSRP: $130

Dr. Scholl's - Feel Engaged. Color Dark Tan Leather. On sale for $78.81. MSRP $130.00. 39% off. 5.0 out of 5 stars

Dr. Scholl's Feel Engaged

Dr. Scholl's Feel Engaged

Brand Name: Dr. Scholl's
Product Name: Feel Engaged
Gender: Men's
Color: Dark Tan Leather
Price: $78.81MSRP: $130

Nunn Bush - Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up. Color Cognac. On sale for $74.38. MSRP $100.00. 26% off. 4.0 out of 5 stars

Nunn Bush Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

Nunn Bush Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

Brand Name: Nunn Bush
Product Name: Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up
Gender: Men's
Color: Cognac
Price: $74.38MSRP: $100

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $85.75. MSRP $104.95. 18% off. 4.7 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: $85.75MSRP: $104.95

Dr. Scholl's - Jake Retro. Color White Grey Fabric. Low Stock. On sale for $58.51. MSRP $105.00. 44% 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: $58.51MSRP: $105

Dr. Scholl's - Jake Oxford. Color Brown Smooth. Low Stock. On sale for $69.99. MSRP $100.00. 30% off.

Low Stock

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: $69.99MSRP: $100

Mephisto - Gerome. Color Light Grey. Low Stock. On sale for $350.10. MSRP $389.00. 10% off.

Low Stock

Mephisto Gerome

Mephisto Gerome

Brand Name: Mephisto
Product Name: Gerome
Gender: Men's
Color: Light Grey
Price: $350.10MSRP: $389

Stacy Adams - Prichard Penny Slip-On. Color Purple Multi. Low Stock. On sale for $116.49. MSRP $130.00. 10% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Prichard Penny Slip-On

Stacy Adams Prichard Penny Slip-On

Brand Name: Stacy Adams
Product Name: Prichard Penny Slip-On
Gender: Men's
Color: Purple Multi
Price: $116.49MSRP: $130

Stacy Adams - Prichard Penny Slip-On. Color Navy Multi. Low Stock. On sale for $114.40. MSRP $130.00. 12% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Prichard Penny Slip-On

Stacy Adams Prichard Penny Slip-On

Brand Name: Stacy Adams
Product Name: Prichard Penny Slip-On
Gender: Men's
Color: Navy Multi
Price: $114.40MSRP: $130

Deer Stags - Infinity. Color Black. On sale for $54.99. MSRP $64.99. 15% off. 4.7 out of 5 stars

Deer Stags Infinity

Deer Stags Infinity

Brand Name: Deer Stags
Product Name: Infinity
Gender: Men's
Color: Black
Price: $54.99MSRP: $64.99

Superga - 2750 OG. Color White/Full Avorio. On sale for $59.50. MSRP $85.00. 30% off. 2.0 out of 5 stars

Superga 2750 OG

Superga 2750 OG

Brand Name: Superga
Product Name: 2750 OG
Gender: Unisex
Color: White/Full Avorio
Price: $59.50MSRP: $85

Superga - 2750 OG. Color Black/White Avorio. On sale for $59.50. MSRP $85.00. 30% off. 2.0 out of 5 stars

Superga 2750 OG

Superga 2750 OG

Brand Name: Superga
Product Name: 2750 OG
Gender: Unisex
Color: Black/White Avorio
Price: $59.50MSRP: $85

Superga - 2750 OG. Color Navy/Full Avorio. Low Stock. On sale for $59.50. MSRP $85.00. 30% off. 2.0 out of 5 stars

Low Stock

Superga 2750 OG

Superga 2750 OG

Brand Name: Superga
Product Name: 2750 OG
Gender: Unisex
Color: Navy/Full Avorio
Price: $59.50MSRP: $85

Cole Haan - Original Grand 2.0 Wing Tip Oxford. Color Black. On sale for $160.80. MSRP $240.00. 33% off. 2.0 out of 5 stars

Cole Haan Original Grand 2.0 Wing Tip Oxford

Cole Haan Original Grand 2.0 Wing Tip Oxford

Brand Name: Cole Haan
Product Name: Original Grand 2.0 Wing Tip Oxford
Gender: Men's
Color: Black
Price: $160.80MSRP: $240

Orthofeet - Dolomite. Color Brown. On sale for $112.46. MSRP $149.95. 25% off. 3.6 out of 5 stars

Orthofeet Dolomite

Orthofeet Dolomite

Brand Name: Orthofeet
Product Name: Dolomite
Gender: Men's
Color: Brown
Price: $112.46MSRP: $149.95

Propet - Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe. Color Sport White. On sale for $80.70. MSRP $107.49. 25% off. 4.4 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: Sport White
Price: $80.70MSRP: $107.49

Propet - Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe. Color White. On sale for $80.70. MSRP $107.49. 25% off. 4.4 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: White
Price: $80.70MSRP: $107.49

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

Nunn Bush - Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up. Color Black. On sale for $59.95. MSRP $90.00. 33% off. 3.5 out of 5 stars

Nunn Bush Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up

Nunn Bush Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up

Brand Name: Nunn Bush
Product Name: Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up
Gender: Men's
Color: Black
Price: $59.95MSRP: $90

Nunn Bush - Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up. Color Taupe. On sale for $59.99. MSRP $90.00. 33% off. 3.5 out of 5 stars

Nunn Bush Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up

Nunn Bush Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up

Brand Name: Nunn Bush
Product Name: Ponte Knit Moc Toe Sneakers Hybrid Oxford Casual Lightweight Athletic Style Lace Up
Gender: Men's
Color: Taupe
Price: $59.99MSRP: $90

Propet - Propet One Evolve. Color Grey/Navy. On sale for $105.57. MSRP $137.49. 23% off. 3.5 out of 5 stars

Propet Propet One Evolve

Propet Propet One Evolve

Brand Name: Propet
Product Name: Propet One Evolve
Gender: Men's
Color: Grey/Navy
Price: $105.57MSRP: $137.49

Propet - Propet One Evolve. Color Black Steel. On sale for $112.61. MSRP $137.49. 18% off. 3.5 out of 5 stars

Propet Propet One Evolve

Propet Propet One Evolve

Brand Name: Propet
Product Name: Propet One Evolve
Gender: Men's
Color: Black Steel
Price: $112.61MSRP: $137.49

ECCO - Gruuv Studio Wingtip Sneaker. Color Cocoa Brown/Mocha. Low Stock. On sale for $157.50. MSRP $194.95. 19% 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: $157.50MSRP: $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

Dansko - Trevor. Color White Calf. On sale for $122.46. MSRP $174.95. 30% off. 2.7 out of 5 stars

Dansko Trevor

Dansko Trevor

Brand Name: Dansko
Product Name: Trevor
Gender: Men's
Color: White Calf
Price: $122.46MSRP: $174.95

SKECHERS - Craster Lanigan Hands Free Slip-Ins. Color Black. On sale for $81.79. MSRP $96.00. 15% 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: $81.79MSRP: $96

PIKOLINOS - Fuencarral M4A. Color Brandy 1. On sale for $150.00. MSRP $200.00. 25% off. 3.0 out of 5 stars

PIKOLINOS Fuencarral M4A

PIKOLINOS Fuencarral M4A

Brand Name: PIKOLINOS
Product Name: Fuencarral M4A
Gender: Men's
Color: Brandy 1
Price: $150MSRP: $200

Cole Haan - Originalgrand Cityspectre Wingtip Oxfords. Color Morel Nubuck/Dark Natural/Silver Birch. On sale for $171.00. MSRP $190.00. 10% off. 4.0 out of 5 stars

Cole Haan Originalgrand Cityspectre Wingtip Oxfords

Cole Haan Originalgrand Cityspectre Wingtip Oxfords

Brand Name: Cole Haan
Product Name: Originalgrand Cityspectre Wingtip Oxfords
Gender: Men's
Color: Morel Nubuck/Dark Natural/Silver Birch
Price: $171MSRP: $190

SKECHERS - Pro 6 SL. Color Off-White. On sale for $103.06. MSRP $129.99. 21% 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: $103.06MSRP: $129.99

SKECHERS - Pro 6 SL. Color Black/Grey. Low Stock. On sale for $98.37. MSRP $129.99. 24% 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: $98.37MSRP: $129.99

Stacy Adams - Sync Lace-Up. Color Natural. On sale for $86.99. MSRP $125.00. 30% 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: $86.99MSRP: $125

Dr. Scholl's - Madison Men Oxford Derby. Color Light Tan Faux Leather. Low Stock. On sale for $52.78. MSRP $95.00. 44% off.

Low Stock

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: $52.78MSRP: $95

Magnanni - Raso II. Color Midbrown. Low Stock. On sale for $212.50. MSRP $425.00. 50% off. 3.0 out of 5 stars

Low Stock

Magnanni Raso II

Magnanni Raso II

Brand Name: Magnanni
Product Name: Raso II
Gender: Men's
Color: Midbrown
Price: $212.50MSRP: $425

SKECHERS - Drive 6 Relaxed Fit Spikeless Golf Shoe. Color Gray. On sale for $94.50. MSRP $115.00. 18% 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: $94.50MSRP: $115

SKECHERS - Elite 6 Slip-In ArchFit Golf Shoe. Color White. On sale for $114.04. MSRP $140.00. 19% off. 5.0 out of 5 stars

SKECHERS Elite 6 Slip-In ArchFit Golf Shoe

SKECHERS Elite 6 Slip-In ArchFit Golf Shoe

Brand Name: SKECHERS
Product Name: Elite 6 Slip-In ArchFit Golf Shoe
Gender: Men's
Color: White
Price: $114.04MSRP: $140

SKECHERS - Elite Vortex Rival ArchFit Golf Shoe. Color Black. On sale for $100.59. 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: Black
Price: $100.59MSRP: $115

SKECHERS - Drive 6 Relaxed Fit Spikeless Golf Shoe. Color Black/White. On sale for $89.16. MSRP $115.00. 22% 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: $89.16MSRP: $115

SKECHERS - Arch Fit 2.0 Look Ahead Hands Free Slip-In. Color Black/Black. On sale for $89.77. MSRP $105.00. 15% 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: $89.77MSRP: $105

Stacy Adams - Tallero Lace-Up. Color Burgundy Multi. Low Stock. On sale for $81.30. MSRP $115.00. 29% 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: $81.30MSRP: $115

Stacy Adams - Tallero Lace-Up. Color Tan Multi. Low Stock. On sale for $78.94. MSRP $115.00. 31% 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: $78.94MSRP: $115

Stacy Adams - Spencer Penny Slip-On. Color Navy. Low Stock. On sale for $93.66. MSRP $130.00. 28% off. 4.8 out of 5 stars

Low Stock

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: $93.66MSRP: $130