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Boots on Sale $50 & Under

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Size 9.5 Office & Career Comfort Shoes

28 items found

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Kenneth Cole - Armand. Color Medium Brown. On sale for $73.32. MSRP $108.95. 33% off. 5.0 out of 5 stars

Kenneth Cole Armand

Kenneth Cole Armand

Brand Name: Kenneth Cole
Product Name: Armand
Gender: Men's
Color: Medium Brown
Price: $73.32MSRP: $108.95

Johnston & Murphy - Archer Cap Toe. Color Cognac. On sale for $125.10. MSRP $139.00. 10% off.

Johnston & Murphy Archer Cap Toe

Johnston & Murphy Archer Cap Toe

Brand Name: Johnston & Murphy
Product Name: Archer Cap Toe
Gender: Men's
Color: Cognac
Price: $125.10MSRP: $139

Cole Haan - Judson Grand Wingtip Oxfords. Color Black Scotch Grain/Black. On sale for $180.21. MSRP $225.00. 20% off.

Cole Haan Judson Grand Wingtip Oxfords

Cole Haan Judson Grand Wingtip Oxfords

Brand Name: Cole Haan
Product Name: Judson Grand Wingtip Oxfords
Gender: Men's
Color: Black Scotch Grain/Black
Price: $180.21MSRP: $225

Dr. Scholl's - Sync Chill Slip On Loafer. Color Tan Smooth. Low Stock. On sale for $72.34. MSRP $90.00. 20% off. 3.7 out of 5 stars

Low Stock

Dr. Scholl's Sync Chill Slip On Loafer

Dr. Scholl's Sync Chill Slip On Loafer

Brand Name: Dr. Scholl's
Product Name: Sync Chill Slip On Loafer
Gender: Men's
Color: Tan Smooth
Price: $72.34MSRP: $90

Florsheim - Renegade Moc Toe Penny Loafer. Color Cognac Multi. On sale for $108.75. MSRP $145.00. 25% off. 4.0 out of 5 stars

Florsheim Renegade Moc Toe Penny Loafer

Florsheim Renegade Moc Toe Penny Loafer

Brand Name: Florsheim
Product Name: Renegade Moc Toe Penny Loafer
Gender: Men's
Color: Cognac Multi
Price: $108.75MSRP: $145

Johnston & Murphy - Gibbons Wingtip. Color Black Full Grain. On sale for $90.30. MSRP $129.00. 30% off. 3.8 out of 5 stars

Johnston & Murphy Gibbons Wingtip

Johnston & Murphy Gibbons Wingtip

Brand Name: Johnston & Murphy
Product Name: Gibbons Wingtip
Gender: Men's
Color: Black Full Grain
Price: $90.30MSRP: $129

Kenneth Cole - Armand. Color Black. On sale for $80.88. MSRP $108.95. 26% off. 5.0 out of 5 stars

Kenneth Cole Armand

Kenneth Cole Armand

Brand Name: Kenneth Cole
Product Name: Armand
Gender: Men's
Color: Black
Price: $80.88MSRP: $108.95

Kenneth Cole - Wilhem. Color Mocha. On sale for $99.00. MSRP $164.95. 40% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Mocha
Price: $99MSRP: $164.95

Kenneth Cole - Wilhem. Color Light Brown. On sale for $99.00. MSRP $164.95. 40% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Light Brown
Price: $99MSRP: $164.95

Clarks - Radcliff Low. Color Black Leather. On sale for $99.00. MSRP $110.00. 10% off.

Clarks Radcliff Low

Clarks Radcliff Low

Brand Name: Clarks
Product Name: Radcliff Low
Gender: Men's
Color: Black Leather
Price: $99MSRP: $110

Clarks - Radcliff Low. Color Tan Leather. On sale for $69.97. MSRP $110.00. 36% off.

Clarks Radcliff Low

Clarks Radcliff Low

Brand Name: Clarks
Product Name: Radcliff Low
Gender: Men's
Color: Tan Leather
Price: $69.97MSRP: $110

Kenneth Cole - Nio Wing Lace Up Oxford. Color Black Leather. Low Stock. On sale for $98.05. MSRP $108.95. 10% off.

Low Stock

Kenneth Cole Nio Wing Lace Up Oxford

Kenneth Cole Nio Wing Lace Up Oxford

Brand Name: Kenneth Cole
Product Name: Nio Wing Lace Up Oxford
Gender: Men's
Color: Black Leather
Price: $98.05MSRP: $108.95

Kenneth Cole - Beautiful Ballad Loafer. Color Medium Brown. On sale for $69.30. MSRP $98.95. 30% off. 5.0 out of 5 stars

Kenneth Cole Beautiful Ballad Loafer

Kenneth Cole Beautiful Ballad Loafer

Brand Name: Kenneth Cole
Product Name: Beautiful Ballad Loafer
Gender: Men's
Color: Medium Brown
Price: $69.30MSRP: $98.95

Stacy Adams - Asher Wingtip Lace Oxford. Color Cognac. Low Stock. On sale for $96.05. MSRP $130.00. 26% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Asher Wingtip Lace Oxford

Stacy Adams Asher Wingtip Lace Oxford

Brand Name: Stacy Adams
Product Name: Asher Wingtip Lace Oxford
Gender: Men's
Color: Cognac
Price: $96.05MSRP: $130

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $31.48. MSRP $104.95. 70% 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: $31.48MSRP: $104.95

Cole Haan - Judson Grand Wingtip Oxfords. Color Raven Suede/Dark Natural. On sale for $146.25. MSRP $225.00. 35% off.

Cole Haan Judson Grand Wingtip Oxfords

Cole Haan Judson Grand Wingtip Oxfords

Brand Name: Cole Haan
Product Name: Judson Grand Wingtip Oxfords
Gender: Men's
Color: Raven Suede/Dark Natural
Price: $146.25MSRP: $225

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Gray Multi. Low Stock. On sale for $108.23. MSRP $130.00. 17% off. 4.4 out of 5 stars

Low Stock

Stacy Adams Reynolds Cap Toe Lace-Up

Stacy Adams Reynolds Cap Toe Lace-Up

Brand Name: Stacy Adams
Product Name: Reynolds Cap Toe Lace-Up
Gender: Men's
Color: Gray Multi
Price: $108.23MSRP: $130

Cole Haan - Chamberlin Grand Plain Toe Oxfords. Color British Tan Nubuck/Black Water Resistant. On sale for $128.05. MSRP $130.00. 1% off.

Cole Haan Chamberlin Grand Plain Toe Oxfords

Cole Haan Chamberlin Grand Plain Toe Oxfords

Brand Name: Cole Haan
Product Name: Chamberlin Grand Plain Toe Oxfords
Gender: Men's
Color: British Tan Nubuck/Black Water Resistant
Price: $128.05MSRP: $130

Born - Cambridge. Color Dark Brown (Braken). Low Stock. On sale for $121.50. MSRP $135.00. 10% off.

Low Stock

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Dark Brown (Braken)
Price: $121.50MSRP: $135

ECCO - St.1 Hybrid Penny Loafer. Color Night Sky. Low Stock. On sale for $118.31. MSRP $250.00. 53% off. 5.0 out of 5 stars

Low Stock

ECCO St.1 Hybrid Penny Loafer

ECCO St.1 Hybrid Penny Loafer

Brand Name: ECCO
Product Name: St.1 Hybrid Penny Loafer
Gender: Men's
Color: Night Sky
Price: $118.31MSRP: $250

Marc Joseph New York - Wall St 3.0. Color Black Napa. Low Stock. On sale for $97.50. MSRP $195.00. 50% off.

Low Stock

Marc Joseph New York Wall St 3.0

Marc Joseph New York Wall St 3.0

Brand Name: Marc Joseph New York
Product Name: Wall St 3.0
Gender: Men's
Color: Black Napa
Price: $97.50MSRP: $195

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $107.07. MSRP $120.00. 11% off. 5.0 out of 5 stars

Cole Haan Bedford Plain-Toe Oxford

Cole Haan Bedford Plain-Toe Oxford

Brand Name: Cole Haan
Product Name: Bedford Plain-Toe Oxford
Gender: Men's
Color: British Tan
Price: $107.07MSRP: $120

Kenneth Cole - Winston. Color Mocha Multi. On sale for $122.92. MSRP $159.95. 23% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Mocha Multi
Price: $122.92MSRP: $159.95

Kenneth Cole - Winston. Color Dark Brown Multi. $159.95.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Dark Brown Multi
Price: $159.95

Florsheim - Highland Plain Toe Oxford. Color Cognac Smooth/White Sole. On sale for $102.00. MSRP $120.00. 15% off. 4.4 out of 5 stars

Florsheim Highland Plain Toe Oxford

Florsheim Highland Plain Toe Oxford

Brand Name: Florsheim
Product Name: Highland Plain Toe Oxford
Gender: Men's
Color: Cognac Smooth/White Sole
Price: $102MSRP: $120

Johnston & Murphy - Sullivan Cap Toe. Color Espresso Italian Calfskin. On sale for $179.10. MSRP $199.00. 10% off.

Johnston & Murphy Sullivan Cap Toe

Johnston & Murphy Sullivan Cap Toe

Brand Name: Johnston & Murphy
Product Name: Sullivan Cap Toe
Gender: Men's
Color: Espresso Italian Calfskin
Price: $179.10MSRP: $199

Stacy Adams - Savian Velour Slip-On. Color Black. On sale for $55.52. MSRP $90.00. 38% off. 5.0 out of 5 stars

Stacy Adams Savian Velour Slip-On

Stacy Adams Savian Velour Slip-On

Brand Name: Stacy Adams
Product Name: Savian Velour Slip-On
Gender: Men's
Color: Black
Price: $55.52MSRP: $90

Johnston & Murphy - Jenson Plain Toe. Color Gray Italian Suede. On sale for $179.00. MSRP $285.00. 37% 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: $179MSRP: $285