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Boots on Sale $50 & Under

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Size 9.5 Office & Career Round Toe Shoes

22 items found

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Kenneth Cole - Beautiful Ballad Loafer. Color Medium Brown. On sale for $59.71. MSRP $98.95. 40% 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: $59.71MSRP: $98.95

Deer Stags - Oakland. Color Brown. On sale for $56.00. MSRP $90.00. 38% off. 3.0 out of 5 stars

Deer Stags Oakland

Deer Stags Oakland

Brand Name: Deer Stags
Product Name: Oakland
Gender: Men's
Color: Brown
Price: $56MSRP: $90

Cole Haan - Grand Remix Oxfords. Color Dark Chocolate/Silver Birch. On sale for $117.00. MSRP $130.00. 10% off. 4.5 out of 5 stars

Cole Haan Grand Remix Oxfords

Cole Haan Grand Remix Oxfords

Brand Name: Cole Haan
Product Name: Grand Remix Oxfords
Gender: Men's
Color: Dark Chocolate/Silver Birch
Price: $117MSRP: $130

Cole Haan - Modern Essentials Wing Oxford. Color Black Waterproof. On sale for $164.99. MSRP $180.00. 8% off. 5.0 out of 5 stars

Cole Haan Modern Essentials Wing Oxford

Cole Haan Modern Essentials Wing Oxford

Brand Name: Cole Haan
Product Name: Modern Essentials Wing Oxford
Gender: Men's
Color: Black Waterproof
Price: $164.99MSRP: $180

Johnston & Murphy - Cormac Cap Toe. Color Brown/Tan Italian Calfskin. Low Stock. On sale for $172.42. MSRP $229.90. 25% off. 4.7 out of 5 stars

Low Stock

Johnston & Murphy Cormac Cap Toe

Johnston & Murphy Cormac Cap Toe

Brand Name: Johnston & Murphy
Product Name: Cormac Cap Toe
Gender: Men's
Color: Brown/Tan Italian Calfskin
Price: $172.42MSRP: $229.90

Stacy Adams - Glendon Slip-On Loafer. Color Blue. Low Stock. On sale for $76.96. MSRP $109.95. 30% off. 5.0 out of 5 stars

Low Stock

Stacy Adams Glendon Slip-On Loafer

Stacy Adams Glendon Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Glendon Slip-On Loafer
Gender: Men's
Color: Blue
Price: $76.96MSRP: $109.95

Florsheim - Renegade Moc Toe Penny Loafer. Color Cognac Multi. On sale for $115.56. MSRP $145.00. 20% off. 4.3 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: $115.56MSRP: $145

Rockport - Cacey. Color Dark Blue. Low Stock. On sale for $125.95. MSRP $139.95. 10% off. 5.0 out of 5 stars

Low Stock

Rockport Cacey

Rockport Cacey

Brand Name: Rockport
Product Name: Cacey
Gender: Men's
Color: Dark Blue
Price: $125.95MSRP: $139.95

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $77.58. MSRP $104.95. 26% 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: $77.58MSRP: $104.95

Magnanni - Leone. Color Tabaco. Low Stock. On sale for $427.50. MSRP $475.00. 10% off.

Low Stock

Magnanni Leone

Magnanni Leone

Brand Name: Magnanni
Product Name: Leone
Gender: Men's
Color: Tabaco
Price: $427.50MSRP: $475

Stacy Adams - Kinsley. Color Black. Low Stock. On sale for $79.99. MSRP $90.00. 11% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Kinsley

Stacy Adams Kinsley

Brand Name: Stacy Adams
Product Name: Kinsley
Gender: Men's
Color: Black
Price: $79.99MSRP: $90

Clarks - Whiddon Cap. Color Mahogany Leather. On sale for $76.00. MSRP $95.00. 20% 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: $76MSRP: $95

Johnston & Murphy - Flynch Cap Toe. Color Tan Italian Calfskin. Low Stock. On sale for $268.20. MSRP $298.00. 10% off. 3.1 out of 5 stars

Low Stock

Johnston & Murphy Flynch Cap Toe

Johnston & Murphy Flynch Cap Toe

Brand Name: Johnston & Murphy
Product Name: Flynch Cap Toe
Gender: Men's
Color: Tan Italian Calfskin
Price: $268.20MSRP: $298

COACH - Cooper Loafer. Color Black. $275.00.

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black
Price: $275

Magnanni - Malta. Color Cognac. On sale for $299.99. MSRP $465.00. 35% off.

Magnanni Malta

Magnanni Malta

Brand Name: Magnanni
Product Name: Malta
Gender: Men's
Color: Cognac
Price: $299.99MSRP: $465

PIKOLINOS - Navarra M8C. Color Brandy 1. Low Stock. On sale for $189.00. MSRP $210.00. 10% off. 1.0 out of 5 stars

Low Stock

PIKOLINOS Navarra M8C

PIKOLINOS Navarra M8C

Brand Name: PIKOLINOS
Product Name: Navarra M8C
Gender: Men's
Color: Brandy 1
Price: $189MSRP: $210

PIKOLINOS - Navarra M8C. Color Black 1. Low Stock. On sale for $189.00. MSRP $210.00. 10% off. 1.0 out of 5 stars

Low Stock

PIKOLINOS Navarra M8C

PIKOLINOS Navarra M8C

Brand Name: PIKOLINOS
Product Name: Navarra M8C
Gender: Men's
Color: Black 1
Price: $189MSRP: $210

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $102.53. 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: $102.53MSRP: $120

Johnston & Murphy - Cormac Cap Toe. Color Black Italian Calfskin. On sale for $236.00. MSRP $295.00. 20% off. 4.7 out of 5 stars

Johnston & Murphy Cormac Cap Toe

Johnston & Murphy Cormac Cap Toe

Brand Name: Johnston & Murphy
Product Name: Cormac Cap Toe
Gender: Men's
Color: Black Italian Calfskin
Price: $236MSRP: $295

Johnston & Murphy - Jenson Plain Toe. Color Tan European Calfskin. On sale for $247.50. MSRP $275.00. 10% off. 4.1 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: Tan European Calfskin
Price: $247.50MSRP: $275

Johnston & Murphy - Jenson Longwing. Color Tan European Calfskin. On sale for $247.50. MSRP $275.00. 10% off. 4.1 out of 5 stars

Johnston & Murphy Jenson Longwing

Johnston & Murphy Jenson Longwing

Brand Name: Johnston & Murphy
Product Name: Jenson Longwing
Gender: Men's
Color: Tan European Calfskin
Price: $247.50MSRP: $275

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