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Boots on Sale $50 & Under

Shop Boots Deals

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Size 9.5 Medium Size Office & Career Shoes

28 items found

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Clarks - Whiddon Cap. Color Mahogany Leather. On sale for $77.99. MSRP $95.00. 18% 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: $77.99MSRP: $95

Cole Haan - Chamberlin Grand Plain Toe Oxfords. Color British Tan Nubuck/Black Water Resistant. On sale for $116.07. MSRP $130.00. 11% 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: $116.07MSRP: $130

PIKOLINOS - Navarra M8C. Color Blue 1. Low Stock. On sale for $63.00. MSRP $210.00. 70% 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: Blue 1
Price: $63MSRP: $210

PIKOLINOS - Navarra M8C. Color Black 1. Low Stock. On sale for $105.00. MSRP $210.00. 50% 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: $105MSRP: $210

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $98.14. MSRP $120.00. 18% 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: $98.14MSRP: $120

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $83.24. MSRP $104.95. 21% 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: $83.24MSRP: $104.95

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 $116.65. MSRP $145.00. 20% 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: $116.65MSRP: $145

Nunn Bush - Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up. Color Cognac. On sale for $74.38. MSRP $100.00. 26% off. 4.0 out of 5 stars

Nunn Bush Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

Nunn Bush Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up

Brand Name: Nunn Bush
Product Name: Stark Cap Toe Oxford Leather Business Formal Derby Dress Casual Lace-Up
Gender: Men's
Color: Cognac
Price: $74.38MSRP: $100

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

Johnston & Murphy - Gibbons Wingtip. Color Tan Hand/Stained 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: Tan Hand/Stained Full Grain
Price: $116.10MSRP: $129

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

Cole Haan - Morse Grand Chukka Boots. Color Morel Suede/Ivory. Low Stock. On sale for $133.20. MSRP $148.00. 10% off.

Low Stock

Cole Haan Morse Grand Chukka Boots

Cole Haan Morse Grand Chukka Boots

Brand Name: Cole Haan
Product Name: Morse Grand Chukka Boots
Gender: Men's
Color: Morel Suede/Ivory
Price: $133.20MSRP: $148

Cole Haan - Grand Remix Oxford. Color Raven Nubuck/Quiet Shade/Paloma. Low Stock. On sale for $117.00. MSRP $130.00. 10% off. 4.7 out of 5 stars

Low Stock

Cole Haan Grand Remix Oxford

Cole Haan Grand Remix Oxford

Brand Name: Cole Haan
Product Name: Grand Remix Oxford
Gender: Men's
Color: Raven Nubuck/Quiet Shade/Paloma
Price: $117MSRP: $130

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

Cole Haan - Judson Grand Wingtip Oxfords. Color Black Scotch Grain/Black. On sale for $172.17. MSRP $225.00. 23% 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: $172.17MSRP: $225

Cole Haan - Judson Grand Wingtip Oxfords. Color Raven Suede/Dark Natural. On sale for $172.29. MSRP $225.00. 23% 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: $172.29MSRP: $225

Dr. Scholl's - Sync Chill Slip On Loafer. Color Tan Smooth. On sale for $65.04. MSRP $90.00. 28% off. 3.7 out of 5 stars

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: $65.04MSRP: $90

PIKOLINOS - Navarra M8C. Color Brandy 1. Low Stock. On sale for $105.00. MSRP $210.00. 50% 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: $105MSRP: $210

Kenneth Cole - Wilhem. Color Mocha. On sale for $132.00. MSRP $164.95. 20% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Mocha
Price: $132MSRP: $164.95

Kenneth Cole - Wilhem. Color Light Brown. On sale for $132.00. MSRP $164.95. 20% off.

Kenneth Cole Wilhem

Kenneth Cole Wilhem

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Light Brown
Price: $132MSRP: $164.95

Kenneth Cole - Winston. Color Mocha Multi. On sale for $111.45. MSRP $159.95. 30% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Mocha Multi
Price: $111.45MSRP: $159.95

Kenneth Cole - Winston. Color Dark Brown Multi. On sale for $108.49. MSRP $159.95. 32% off.

Kenneth Cole Winston

Kenneth Cole Winston

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Dark Brown Multi
Price: $108.49MSRP: $159.95

Kenneth Cole - Armand. Color Medium Brown. On sale for $70.81. MSRP $108.95. 35% 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: $70.81MSRP: $108.95

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Gray Multi. Low Stock. On sale for $91.00. MSRP $130.00. 30% 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: $91MSRP: $130

Johnston & Murphy - Jenson Plain Toe. Color Gray Italian Suede. On sale for $213.75. MSRP $285.00. 25% 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: $213.75MSRP: $285

Deer Stags - Uplift. Color Brown/Dark Brown. On sale for $84.68. MSRP $90.00. 6% off.

Deer Stags Uplift

Deer Stags Uplift

Brand Name: Deer Stags
Product Name: Uplift
Gender: Men's
Color: Brown/Dark Brown
Price: $84.68MSRP: $90

ECCO - St.1 Hybrid Penny Loafer. Color Night Sky. Low Stock. On sale for $123.20. MSRP $250.00. 51% 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: $123.20MSRP: $250