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Boots on Sale $50 & Under

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Size 8.5 Arch Support Casual Shoes On Sale

38 items found

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Stacy Adams - Spencer Penny Slip-On. Color Burgundy. Low Stock. On sale for $60.00. MSRP $130.00. 54% 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: Burgundy
Price: $60MSRP: $130

Dansko - Sigourney. Color Honey Distressed. On sale for $123.95. MSRP $184.95. 33% off. 3.5 out of 5 stars

Dansko Sigourney

Dansko Sigourney

Brand Name: Dansko
Product Name: Sigourney
Gender: Women's
Color: Honey Distressed
Price: $123.95MSRP: $184.95

Stacy Adams - Edgewood Wing Tip Elastic Lace. Color Black. On sale for $82.39. MSRP $140.00. 41% off. 4.0 out of 5 stars

Stacy Adams Edgewood Wing Tip Elastic Lace

Stacy Adams Edgewood Wing Tip Elastic Lace

Brand Name: Stacy Adams
Product Name: Edgewood Wing Tip Elastic Lace
Gender: Men's
Color: Black
Price: $82.39MSRP: $140

Deer Stags - Infinity. Color Brown. On sale for $45.49. MSRP $64.99. 30% 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: $45.49MSRP: $64.99

Dr. Scholl's - Madison Men Oxford Derby. Color Light Tan Faux Leather. Low Stock. On sale for $53.25. 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: $53.25MSRP: $95

Orthofeet - Leo. Color Black. On sale for $101.50. MSRP $145.00. 30% off. 3.0 out of 5 stars

Orthofeet Leo

Orthofeet Leo

Brand Name: Orthofeet
Product Name: Leo
Gender: Men's
Color: Black
Price: $101.50MSRP: $145

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 Gray. 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: Gray
Price: $59.95MSRP: $90

Stacy Adams - Tallero Lace-Up. Color Tan Multi. Low Stock. On sale for $79.21. 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: $79.21MSRP: $115

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $91.15. MSRP $104.95. 13% 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: $91.15MSRP: $104.95

Stacy Adams - Spencer Penny Slip-On. Color Navy. Low Stock. On sale for $94.45. MSRP $130.00. 27% 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: $94.45MSRP: $130

Marc Joseph New York - Boone Ave. Color Whiskey Grainy. Low Stock. On sale for $77.50. MSRP $155.00. 50% off. 4.0 out of 5 stars

Low Stock

Marc Joseph New York Boone Ave

Marc Joseph New York Boone Ave

Brand Name: Marc Joseph New York
Product Name: Boone Ave
Gender: Men's
Color: Whiskey Grainy
Price: $77.50MSRP: $155

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

Stacy Adams - Edgewood Wing Tip Elastic Lace. Color Taupe. On sale for $103.32. MSRP $140.00. 26% off. 4.0 out of 5 stars

Stacy Adams Edgewood Wing Tip Elastic Lace

Stacy Adams Edgewood Wing Tip Elastic Lace

Brand Name: Stacy Adams
Product Name: Edgewood Wing Tip Elastic Lace
Gender: Men's
Color: Taupe
Price: $103.32MSRP: $140

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

Align - Buckley. Color Cashmere. On sale for $139.45. MSRP $154.95. 10% off. 4.0 out of 5 stars

Align Buckley

Align Buckley

Brand Name: Align
Product Name: Buckley
Gender: Men's
Color: Cashmere
Price: $139.45MSRP: $154.95

Align - Buckley. Color Black. On sale for $139.45. MSRP $154.95. 10% off. 4.0 out of 5 stars

Align Buckley

Align Buckley

Brand Name: Align
Product Name: Buckley
Gender: Men's
Color: Black
Price: $139.45MSRP: $154.95

Stacy Adams - Edgewood Wing Tip Elastic Lace. Color Cognac. On sale for $65.00. MSRP $140.00. 54% off. 4.0 out of 5 stars

Stacy Adams Edgewood Wing Tip Elastic Lace

Stacy Adams Edgewood Wing Tip Elastic Lace

Brand Name: Stacy Adams
Product Name: Edgewood Wing Tip Elastic Lace
Gender: Men's
Color: Cognac
Price: $65MSRP: $140

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Black Suede. On sale for $69.00. MSRP $115.00. 40% off. 4.4 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: $69MSRP: $115

Stacy Adams - Tallero Lace-Up. Color Burgundy Multi. Low Stock. On sale for $92.49. MSRP $115.00. 20% 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: $92.49MSRP: $115

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

Dansko - Sigourney. Color Black Tumbled. On sale for $134.98. MSRP $184.95. 27% off. 3.5 out of 5 stars

Dansko Sigourney

Dansko Sigourney

Brand Name: Dansko
Product Name: Sigourney
Gender: Women's
Color: Black Tumbled
Price: $134.98MSRP: $184.95

Dansko - Lorri. Color Black/Leopard Suede. On sale for $79.72. MSRP $144.95. 45% off. 3.0 out of 5 stars

Dansko Lorri

Dansko Lorri

Brand Name: Dansko
Product Name: Lorri
Gender: Women's
Color: Black/Leopard Suede
Price: $79.72MSRP: $144.95

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

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 - Jake Retro. Color White Grey Fabric. Low Stock. On sale for $60.99. MSRP $105.00. 42% 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: $60.99MSRP: $105

Propet - Life Walker Strap Medicare/HCPCS Code = A5500 Diabetic Shoe. Color White. On sale for $93.18. MSRP $107.49. 13% 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: $93.18MSRP: $107.49

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

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

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

SKECHERS - Pro 6. Color Black. Low Stock. On sale for $107.61. MSRP $145.00. 26% off. 1.0 out of 5 stars

Low Stock

SKECHERS Pro 6

SKECHERS Pro 6

Brand Name: SKECHERS
Product Name: Pro 6
Gender: Men's
Color: Black
Price: $107.61MSRP: $145

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

Mephisto Gerome

Mephisto Gerome

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

KEEN - Waimea TG. Color Cornstalk/Black. On sale for $63.70. 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: $63.70MSRP: $84.95

Stacy Adams - Prichard Penny Slip-On. Color Purple Multi. Low Stock. On sale for $115.44. MSRP $130.00. 11% 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: $115.44MSRP: $130

Stacy Adams - Prichard Penny Slip-On. Color Navy Multi. Low Stock. On sale for $114.45. 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: $114.45MSRP: $130

Stacy Adams - Karnes Penny Slip-On Loafer. Color Black. Low Stock. On sale for $111.04. MSRP $130.00. 15% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Karnes Penny Slip-On Loafer

Stacy Adams Karnes Penny Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Karnes Penny Slip-On Loafer
Gender: Men's
Color: Black
Price: $111.04MSRP: $130

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