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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Size 8.5 Medium Size Office & Career Shoes

24 items found

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Steve Madden - Jabrian. Color Tan. Low Stock. On sale for $39.00. MSRP $130.00. 70% off.

Low Stock

Steve Madden Jabrian

Steve Madden Jabrian

Brand Name: Steve Madden
Product Name: Jabrian
Gender: Men's
Color: Tan
Price: $39MSRP: $130

BILLY Footwear - Work Comfort Lo. Color Black/Black. On sale for $57.78. MSRP $90.00. 36% off. 4.8 out of 5 stars

BILLY Footwear Work Comfort Lo

BILLY Footwear Work Comfort Lo

Brand Name: BILLY Footwear
Product Name: Work Comfort Lo
Gender: Men's
Color: Black/Black
Price: $57.78MSRP: $90

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

Cole Haan - Chamberlin Grand Plain Toe Oxfords. Color British Tan Nubuck/Black Water Resistant. On sale for $123.99. MSRP $130.00. 5% 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: $123.99MSRP: $130

Kenneth Cole - Armand. Color Medium Brown. On sale for $77.99. MSRP $108.95. 28% 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: $77.99MSRP: $108.95

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $101.56. MSRP $120.00. 15% 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: $101.56MSRP: $120

Kenneth Cole - Wilhem. Color Light Brown. On sale for $115.46. MSRP $164.95. 30% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Light Brown
Price: $115.46MSRP: $164.95

Kenneth Cole - Winston. Color Mocha Multi. On sale for $79.97. MSRP $159.95. 50% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Mocha Multi
Price: $79.97MSRP: $159.95

Kenneth Cole - Winston. Color Dark Brown Multi. On sale for $95.97. MSRP $159.95. 40% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Dark Brown Multi
Price: $95.97MSRP: $159.95

Clarks - Whiddon Cap. Color Mahogany Leather. On sale for $80.75. MSRP $95.00. 15% off. 3.8 out of 5 stars

Clarks Whiddon Cap

Clarks Whiddon Cap

Brand Name: Clarks
Product Name: Whiddon Cap
Gender: Men's
Color: Mahogany Leather
Price: $80.75MSRP: $95

Samuel Hubbard - Frequent Traveler Loafer. Color Black. $285.00. 4.5 out of 5 stars

Samuel Hubbard Frequent Traveler Loafer

Samuel Hubbard Frequent Traveler Loafer

Brand Name: Samuel Hubbard
Product Name: Frequent Traveler Loafer
Gender: Men's
Color: Black
Price: $285

Deer Stags - Uplift. Color Brown/Dark Brown. On sale for $81.11. MSRP $90.00. 10% off.

Deer Stags Uplift

Deer Stags Uplift

Brand Name: Deer Stags
Product Name: Uplift
Gender: Men's
Color: Brown/Dark Brown
Price: $81.11MSRP: $90

Marc Joseph New York - Willmington. Color Atlantic Blue Suede. On sale for $79.95. MSRP $185.00. 57% off. 3.8 out of 5 stars

Marc Joseph New York Willmington

Marc Joseph New York Willmington

Brand Name: Marc Joseph New York
Product Name: Willmington
Gender: Men's
Color: Atlantic Blue Suede
Price: $79.95MSRP: $185

Vince Camuto - Lyre. Color Cognac/Brown. Low Stock. On sale for $134.10. MSRP $149.00. 10% off. 4.0 out of 5 stars

Low Stock

Vince Camuto Lyre

Vince Camuto Lyre

Brand Name: Vince Camuto
Product Name: Lyre
Gender: Men's
Color: Cognac/Brown
Price: $134.10MSRP: $149

ECCO - St.1 Hybrid Penny Loafer. Color Night Sky. On sale for $123.23. MSRP $250.00. 51% off. 5.0 out of 5 stars

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: $123.23MSRP: $250

Born - Cambridge. Color Black. Low Stock. On sale for $87.75. MSRP $135.00. 35% off.

Low Stock

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Black
Price: $87.75MSRP: $135

Magnanni - 23037-00. Color Bone Suede. Low Stock. $525.00.

Low Stock

Magnanni 23037-00

Magnanni 23037-00

Brand Name: Magnanni
Product Name: 23037-00
Gender: Men's
Color: Bone Suede
Price: $525

Allen Edmonds - Newman. Color Antique Bronze. Low Stock. On sale for $212.50. MSRP $425.00. 50% off. 4.2 out of 5 stars

Low Stock

Allen Edmonds Newman

Allen Edmonds Newman

Brand Name: Allen Edmonds
Product Name: Newman
Gender: Men's
Color: Antique Bronze
Price: $212.50MSRP: $425

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

Cole Haan - Judson Grand Wingtip Oxfords. Color Black Scotch Grain/Black. On sale for $196.55. MSRP $225.00. 13% 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: $196.55MSRP: $225

Cole Haan - Judson Grand Wingtip Oxfords. Color Raven Suede/Dark Natural. On sale for $188.54. MSRP $225.00. 16% 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: $188.54MSRP: $225

Johnston & Murphy - Gibbons Wingtip. Color Black Full Grain. On sale for $116.10. MSRP $129.00. 10% 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: $116.10MSRP: $129

Florsheim - Renegade Moc Toe Penny Loafer. Color Cognac Multi. On sale for $118.14. MSRP $145.00. 19% 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: $118.14MSRP: $145

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