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Boots on Sale $50 & Under

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Size 8.5 Medium Size Leather Shoes

620 items found

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ECCO - Seoul Plain Toe Oxford. Color Nutmeg Brown Suede. On sale for $159.04. MSRP $224.95. 29% off. 5.0 out of 5 stars

ECCO Seoul Plain Toe Oxford

ECCO Seoul Plain Toe Oxford

Brand Name: ECCO
Product Name: Seoul Plain Toe Oxford
Gender: Men's
Color: Nutmeg Brown Suede
Price: $159.04MSRP: $224.95

Columbia - Trailstorm Ascend Waterproof Mid. Color Graphite/Nori. On sale for $93.88. MSRP $100.00. 6% off. 3.2 out of 5 stars

Columbia Trailstorm Ascend Waterproof Mid

Columbia Trailstorm Ascend Waterproof Mid

Brand Name: Columbia
Product Name: Trailstorm Ascend Waterproof Mid
Gender: Men's
Color: Graphite/Nori
Price: $93.88MSRP: $100

Stacy Adams - Prichard Penny Slip-On. Color Purple Multi. Low Stock. On sale for $118.29. MSRP $130.00. 9% 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: $118.29MSRP: $130

Stacy Adams - Brinkley Moc Toe Slip-On. Color Tan. Low Stock. On sale for $102.82. MSRP $145.00. 29% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Brinkley Moc Toe Slip-On

Stacy Adams Brinkley Moc Toe Slip-On

Brand Name: Stacy Adams
Product Name: Brinkley Moc Toe Slip-On
Gender: Men's
Color: Tan
Price: $102.82MSRP: $145

Stacy Adams - Brinkley Moc Toe Slip-On. Color Navy. Low Stock. On sale for $99.98. MSRP $145.00. 31% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Brinkley Moc Toe Slip-On

Stacy Adams Brinkley Moc Toe Slip-On

Brand Name: Stacy Adams
Product Name: Brinkley Moc Toe Slip-On
Gender: Men's
Color: Navy
Price: $99.98MSRP: $145

Stacy Adams - Tristano Bike Toe Lace-Up. Color White. On sale for $106.49. MSRP $115.00. 7% off. 4.8 out of 5 stars

Stacy Adams Tristano Bike Toe Lace-Up

Stacy Adams Tristano Bike Toe Lace-Up

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: White
Price: $106.49MSRP: $115

Stacy Adams - Everidge Elastic Lace. Color Olive. On sale for $91.00. MSRP $130.00. 30% off. 4.5 out of 5 stars

Stacy Adams Everidge Elastic Lace

Stacy Adams Everidge Elastic Lace

Brand Name: Stacy Adams
Product Name: Everidge Elastic Lace
Gender: Men's
Color: Olive
Price: $91MSRP: $130

Stacy Adams - Prichard Penny Slip-On. Color Navy Multi. Low Stock. On sale for $113.12. MSRP $130.00. 13% 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: $113.12MSRP: $130

Eastland 1955 Edition - Scarborough. Color Beige. Low Stock. On sale for $56.25. MSRP $125.00. 55% 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: $56.25MSRP: $125

Eastland 1955 Edition - Leap Trainer. Color Sand. On sale for $89.99. MSRP $135.00. 33% off. 1.0 out of 5 stars

Eastland 1955 Edition Leap Trainer

Eastland 1955 Edition Leap Trainer

Brand Name: Eastland 1955 Edition
Product Name: Leap Trainer
Gender: Men's
Color: Sand
Price: $89.99MSRP: $135

Eastland 1955 Edition - Leap Trainer. Color Tan. On sale for $89.99. MSRP $135.00. 33% off. 1.0 out of 5 stars

Eastland 1955 Edition Leap Trainer

Eastland 1955 Edition Leap Trainer

Brand Name: Eastland 1955 Edition
Product Name: Leap Trainer
Gender: Men's
Color: Tan
Price: $89.99MSRP: $135

Johnston & Murphy - Bolivar Venetian. Color Snuff. On sale for $178.75. MSRP $275.00. 35% 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: $178.75MSRP: $275

Johnston & Murphy - Jenson Longwing. Color Tan Italian Calfskin. Low Stock. On sale for $206.50. MSRP $295.00. 30% off. 4.1 out of 5 stars

Low Stock

Johnston & Murphy Jenson Longwing

Johnston & Murphy Jenson Longwing

Brand Name: Johnston & Murphy
Product Name: Jenson Longwing
Gender: Men's
Color: Tan Italian Calfskin
Price: $206.50MSRP: $295

Johnston & Murphy - Bolivar Cap Toe. Color Gray Italian Suede. On sale for $165.00. MSRP $275.00. 40% off.

Johnston & Murphy Bolivar Cap Toe

Johnston & Murphy Bolivar Cap Toe

Brand Name: Johnston & Murphy
Product Name: Bolivar Cap Toe
Gender: Men's
Color: Gray Italian Suede
Price: $165MSRP: $275

Dr. Scholl's - Madison Men Oxford Derby. Color Light Tan Faux Leather. Low Stock. On sale for $61.75. MSRP $95.00. 35% 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: $61.75MSRP: $95

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

Johnston & Murphy - Braydon Plain Toe. Color Grey. Low Stock. On sale for $69.50. MSRP $139.00. 50% off. 4.0 out of 5 stars

Low Stock

Johnston & Murphy Braydon Plain Toe

Johnston & Murphy Braydon Plain Toe

Brand Name: Johnston & Murphy
Product Name: Braydon Plain Toe
Gender: Men's
Color: Grey
Price: $69.50MSRP: $139

SKECHERS - Drive 6 Relaxed Fit Spikeless Golf Shoe. Color Gray. On sale for $98.91. MSRP $115.00. 14% 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: $98.91MSRP: $115

Columbia - Bahama X Relaxed. Color Grey Ice/Sea Salt. On sale for $67.36. MSRP $80.00. 16% off. 4.2 out of 5 stars

Columbia Bahama X Relaxed

Columbia Bahama X Relaxed

Brand Name: Columbia
Product Name: Bahama X Relaxed
Gender: Men's
Color: Grey Ice/Sea Salt
Price: $67.36MSRP: $80

Deer Stags - Uplift. Color Brown/Dark Brown. On sale for $81.51. MSRP $90.00. 9% off.

Deer Stags Uplift

Deer Stags Uplift

Brand Name: Deer Stags
Product Name: Uplift
Gender: Men's
Color: Brown/Dark Brown
Price: $81.51MSRP: $90

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