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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Size 8.5 Office & Career On Sale Products

36 items found

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Johnston & Murphy - Archer Cap Toe. Color Cognac. On sale for $69.50. MSRP $139.00. 50% 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: $69.50MSRP: $139

Kenneth Cole - Armand. Color Black. On sale for $65.40. MSRP $108.95. 40% 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: $65.40MSRP: $108.95

ECCO - St.1 Hybrid Penny Loafer. Color Cognac. Low Stock. On sale for $100.00. MSRP $250.00. 60% 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: Cognac
Price: $100MSRP: $250

Johnston & Murphy - Ellsworth Plain Toe Medallion. Color Brown Italian Calfskin. Low Stock. On sale for $132.75. MSRP $295.00. 55% off. 2.5 out of 5 stars

Low Stock

Johnston & Murphy Ellsworth Plain Toe Medallion

Johnston & Murphy Ellsworth Plain Toe Medallion

Brand Name: Johnston & Murphy
Product Name: Ellsworth Plain Toe Medallion
Gender: Men's
Color: Brown Italian Calfskin
Price: $132.75MSRP: $295

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

Kenneth Cole - Armand. Color Medium Brown. On sale for $65.40. MSRP $108.95. 40% 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: $65.40MSRP: $108.95

Merrell - Jungle Moc Nubuck. Color Brown Nubuck. On sale for $99.00. MSRP $110.00. 10% off. 4.6 out of 5 stars

Merrell Jungle Moc Nubuck

Merrell Jungle Moc Nubuck

Brand Name: Merrell
Product Name: Jungle Moc Nubuck
Gender: Men's
Color: Brown Nubuck
Price: $99MSRP: $110

Steve Madden - Paulson. Color Black. On sale for $121.73. MSRP $130.00. 6% off.

Steve Madden Paulson

Steve Madden Paulson

Brand Name: Steve Madden
Product Name: Paulson
Gender: Men's
Color: Black
Price: $121.73MSRP: $130

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

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

Clarks - Whiddon Apron. Color Black Tumbled. Low Stock. On sale for $69.00. MSRP $95.00. 27% off.

Low Stock

Clarks Whiddon Apron

Clarks Whiddon Apron

Brand Name: Clarks
Product Name: Whiddon Apron
Gender: Men's
Color: Black Tumbled
Price: $69MSRP: $95

ECCO - St.1 Hybrid Penny Loafer. Color Night Sky. On sale for $129.95. MSRP $250.00. 48% 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: $129.95MSRP: $250

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $103.19. MSRP $120.00. 14% 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: $103.19MSRP: $120

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

Massimo Matteo - Almansa Moccasin Bit. Color Black. Low Stock. On sale for $117.00. MSRP $195.00. 40% off. 4.2 out of 5 stars

Low Stock

Massimo Matteo Almansa Moccasin Bit

Massimo Matteo Almansa Moccasin Bit

Brand Name: Massimo Matteo
Product Name: Almansa Moccasin Bit
Gender: Men's
Color: Black
Price: $117MSRP: $195

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

Magnanni - 23037-00. Color Bone Suede. Low Stock. On sale for $446.25. MSRP $525.00. 15% off.

Low Stock

Magnanni 23037-00

Magnanni 23037-00

Brand Name: Magnanni
Product Name: 23037-00
Gender: Men's
Color: Bone Suede
Price: $446.25MSRP: $525

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

Nunn Bush - MAC Moccasin Toe Oxford. Color Black. Low Stock. On sale for $77.78. MSRP $100.00. 22% off. 5.0 out of 5 stars

Low Stock

Nunn Bush MAC Moccasin Toe Oxford

Nunn Bush MAC Moccasin Toe Oxford

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Oxford
Gender: Men's
Color: Black
Price: $77.78MSRP: $100

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $77.95. 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: $77.95MSRP: $104.95

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

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

Vince Camuto - Lyre. Color Cognac/Brown. Low Stock. On sale for $124.77. MSRP $149.00. 16% 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: $124.77MSRP: $149

Stacy Adams - Kallum Cap Toe Oxford. Color Navy. Low Stock. On sale for $106.50. MSRP $130.00. 18% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Kallum Cap Toe Oxford

Stacy Adams Kallum Cap Toe Oxford

Brand Name: Stacy Adams
Product Name: Kallum Cap Toe Oxford
Gender: Men's
Color: Navy
Price: $106.50MSRP: $130

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

Steve Madden - Jabrian. Color Tan. On sale for $82.03. MSRP $130.00. 37% off.

Steve Madden Jabrian

Steve Madden Jabrian

Brand Name: Steve Madden
Product Name: Jabrian
Gender: Men's
Color: Tan
Price: $82.03MSRP: $130

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

BILLY Footwear - Work Comfort Lo. Color Black/Black. On sale for $81.00. MSRP $90.00. 10% 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: $81MSRP: $90

Born - Cambridge. Color Black. On sale for $79.95. MSRP $135.00. 41% off.

Born Cambridge

Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Black
Price: $79.95MSRP: $135

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

Born Cambridge

Born Cambridge

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

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

Rockport - Cacey. Color Grey. Low Stock. On sale for $79.60. MSRP $139.95. 43% off. 5.0 out of 5 stars

Low Stock

Rockport Cacey

Rockport Cacey

Brand Name: Rockport
Product Name: Cacey
Gender: Men's
Color: Grey
Price: $79.60MSRP: $139.95

Johnston & Murphy - Gibbons Wingtip. Color Tan Hand/Stained Full Grain. On sale for $83.85. MSRP $129.00. 35% 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: $83.85MSRP: $129

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Gray Multi. Low Stock. On sale for $78.00. MSRP $130.00. 40% off. 4.0 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: $78MSRP: $130