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Boots on Sale $50 or Less!

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Men's Leather Office & Career Comfort Shoes

49 items found

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BOSS - Colby Smooth Leather Derby Dress Shoes. Color Burnt Caramel. Low Stock. On sale for $179.10. MSRP $199.00..

Low Stock

BOSS Colby Smooth Leather Derby Dress Shoes

BOSS Colby Smooth Leather Derby Dress Shoes

Brand Name: BOSS
Product Name: Colby Smooth Leather Derby Dress Shoes
Gender: Men's
Color: Burnt Caramel
Price: $179.10MSRP: $199.00

Marc Joseph New York - Thomas ST. Color Black Napa. Low Stock. On sale for $113.15. MSRP $155.00..

Low Stock

Marc Joseph New York Thomas ST

Marc Joseph New York Thomas ST

Brand Name: Marc Joseph New York
Product Name: Thomas ST
Gender: Men's
Color: Black Napa
Price: $113.15MSRP: $155.00

Carlos by Carlos Santana - Corazon Chukka Boot. Color Dark Brown Full Grain Calfskin Leather. Low Stock. On sale for $67.73. MSRP $153.95.. 4.2 out of 5 stars

Low Stock

Carlos by Carlos Santana Corazon Chukka Boot

Carlos by Carlos Santana Corazon Chukka Boot

Brand Name: Carlos by Carlos Santana
Product Name: Corazon Chukka Boot
Gender: Men's
Color: Dark Brown Full Grain Calfskin Leather
Price: $67.73MSRP: $153.95

HUGO - Kerr Derby Shoe. Color Dark Brown. On sale for $134.33. MSRP $199.00..

HUGO Kerr Derby Shoe

HUGO Kerr Derby Shoe

Brand Name: HUGO
Product Name: Kerr Derby Shoe
Gender: Men's
Color: Dark Brown
Price: $134.33MSRP: $199.00

Steve Madden - Paulson. Color Black. On sale for $80.65. MSRP $130.00..

Steve Madden Paulson

Steve Madden Paulson

Brand Name: Steve Madden
Product Name: Paulson
Gender: Men's
Color: Black
Price: $80.65MSRP: $130.00

Johnston & Murphy - Lewis Embossed Wing Tip. Color Tan Full Grain. On sale for $83.30. MSRP $119.00.. 5.0 out of 5 stars

Johnston & Murphy Lewis Embossed Wing Tip

Johnston & Murphy Lewis Embossed Wing Tip

Brand Name: Johnston & Murphy
Product Name: Lewis Embossed Wing Tip
Gender: Men's
Color: Tan Full Grain
Price: $83.30MSRP: $119.00

BOSS - Colby Smooth Leather Derby Dress Shoes. Color Black Storm. Low Stock. On sale for $190.05. MSRP $199.00..

Low Stock

BOSS Colby Smooth Leather Derby Dress Shoes

BOSS Colby Smooth Leather Derby Dress Shoes

Brand Name: BOSS
Product Name: Colby Smooth Leather Derby Dress Shoes
Gender: Men's
Color: Black Storm
Price: $190.05MSRP: $199.00

Johnston & Murphy - Kelton Plain Toe Boot. Color Taupe Suede. Low Stock. On sale for $110.05. MSRP $155.00.. 5.0 out of 5 stars

Low Stock

Johnston & Murphy Kelton Plain Toe Boot

Johnston & Murphy Kelton Plain Toe Boot

Brand Name: Johnston & Murphy
Product Name: Kelton Plain Toe Boot
Gender: Men's
Color: Taupe Suede
Price: $110.05MSRP: $155.00

COACH - Cooper Loafer. Color Black / Chalk. Low Stock. On sale for $174.05. MSRP $295.00..

Low Stock

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black / Chalk
Price: $174.05MSRP: $295.00

COACH - Cooper Loafer. Color Black /Chalk. Low Stock. On sale for $221.25. MSRP $295.00..

Low Stock

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black /Chalk
Price: $221.25MSRP: $295.00

COACH - Cooper Loafer. Color Saddle. On sale for $203.60. MSRP $275.00..

COACH Cooper Loafer

COACH Cooper Loafer

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Saddle
Price: $203.60MSRP: $275.00

Johnston & Murphy Collection - Ellsworth Plain Toe Medallion. Color Black Italian Calfskin. Low Stock. On sale for $221.25. MSRP $295.00.. 2.0 out of 5 stars

Low Stock

Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Brand Name: Johnston & Murphy Collection
Product Name: Ellsworth Plain Toe Medallion
Gender: Men's
Color: Black Italian Calfskin
Price: $221.25MSRP: $295.00

Johnston & Murphy Collection - Ellsworth Plain Toe Medallion. Color Brown Italian Calfskin. Low Stock. On sale for $221.25. MSRP $295.00.. 2.0 out of 5 stars

Low Stock

Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Brand Name: Johnston & Murphy Collection
Product Name: Ellsworth Plain Toe Medallion
Gender: Men's
Color: Brown Italian Calfskin
Price: $221.25MSRP: $295.00

Florsheim - Kenmoor Wingtip Oxford. Color Cognac Calf. Low Stock. On sale for $132.50. MSRP $235.00.. 4.5 out of 5 stars

Low Stock

Florsheim Kenmoor Wingtip Oxford

Florsheim Kenmoor Wingtip Oxford

Brand Name: Florsheim
Product Name: Kenmoor Wingtip Oxford
Gender: Men's
Color: Cognac Calf
Price: $132.50MSRP: $235.00

Carlos by Carlos Santana - Corazon Chukka Boot. Color Chocolate Brown. Low Stock. On sale for $80.05. MSRP $153.95.. 4.2 out of 5 stars

Low Stock

Carlos by Carlos Santana Corazon Chukka Boot

Carlos by Carlos Santana Corazon Chukka Boot

Brand Name: Carlos by Carlos Santana
Product Name: Corazon Chukka Boot
Gender: Men's
Color: Chocolate Brown
Price: $80.05MSRP: $153.95

Marc Joseph New York - Thomas ST. Color Chestnut Napa. Low Stock. On sale for $82.15. MSRP $155.00..

Low Stock

Marc Joseph New York Thomas ST

Marc Joseph New York Thomas ST

Brand Name: Marc Joseph New York
Product Name: Thomas ST
Gender: Men's
Color: Chestnut Napa
Price: $82.15MSRP: $155.00

Magnanni - Marcosa. Color Tabaco. Low Stock. On sale for $391.50. MSRP $435.00..

Low Stock

Magnanni Marcosa

Magnanni Marcosa

Brand Name: Magnanni
Product Name: Marcosa
Gender: Men's
Color: Tabaco
Price: $391.50MSRP: $435.00

Florsheim - Postino Cap Toe. Color Cognac Scratch Print. Low Stock. On sale for $97.46. MSRP $130.00.. 4.6 out of 5 stars

Low Stock

Florsheim Postino Cap Toe

Florsheim Postino Cap Toe

Brand Name: Florsheim
Product Name: Postino Cap Toe
Gender: Men's
Color: Cognac Scratch Print
Price: $97.46MSRP: $130.00

Florsheim - Postino Cap Toe. Color Black Scratch Print. Low Stock. On sale for $116.95. MSRP $130.00.. 4.6 out of 5 stars

Low Stock

Florsheim Postino Cap Toe

Florsheim Postino Cap Toe

Brand Name: Florsheim
Product Name: Postino Cap Toe
Gender: Men's
Color: Black Scratch Print
Price: $116.95MSRP: $130.00

Florsheim - Postino Cap Toe. Color Cognac Smooth. On sale for $106.51. MSRP $130.00.. 4.6 out of 5 stars

Florsheim Postino Cap Toe

Florsheim Postino Cap Toe

Brand Name: Florsheim
Product Name: Postino Cap Toe
Gender: Men's
Color: Cognac Smooth
Price: $106.51MSRP: $130.00

Magnanni - Cole Perf. Color Cognac. Low Stock. On sale for $445.50. MSRP $495.00..

Low Stock

Magnanni Cole Perf

Magnanni Cole Perf

Brand Name: Magnanni
Product Name: Cole Perf
Gender: Men's
Color: Cognac
Price: $445.50MSRP: $495.00

Magnanni - Lachlan. Color Grey/Cuero. Low Stock. On sale for $351.55. MSRP $445.00..

Low Stock

Magnanni Lachlan

Magnanni Lachlan

Brand Name: Magnanni
Product Name: Lachlan
Gender: Men's
Color: Grey/Cuero
Price: $351.55MSRP: $445.00

HUGO - Kerr Derby Shoe. Color Black. Low Stock. On sale for $149.25. MSRP $199.00..

Low Stock

HUGO Kerr Derby Shoe

HUGO Kerr Derby Shoe

Brand Name: HUGO
Product Name: Kerr Derby Shoe
Gender: Men's
Color: Black
Price: $149.25MSRP: $199.00

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Gray Multi. On sale for $98.40. MSRP $120.00..

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: $98.40MSRP: $120.00

Stacy Adams - Reynolds Cap Toe Lace-Up. Color Brown/Navy. On sale for $108.00. MSRP $120.00..

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: Brown/Navy
Price: $108.00MSRP: $120.00

Florsheim - Annuity Cap Toe Oxford. Color Burgundy. Low Stock. On sale for $98.77. MSRP $190.00.. 4.8 out of 5 stars

Low Stock

Florsheim Annuity Cap Toe Oxford

Florsheim Annuity Cap Toe Oxford

Brand Name: Florsheim
Product Name: Annuity Cap Toe Oxford
Gender: Men's
Color: Burgundy
Price: $98.77MSRP: $190.00

Johnston & Murphy - Lewis Embossed Wing Tip. Color Black Full Grain. Low Stock. On sale for $89.25. MSRP $119.00.. 5.0 out of 5 stars

Low Stock

Johnston & Murphy Lewis Embossed Wing Tip

Johnston & Murphy Lewis Embossed Wing Tip

Brand Name: Johnston & Murphy
Product Name: Lewis Embossed Wing Tip
Gender: Men's
Color: Black Full Grain
Price: $89.25MSRP: $119.00

Johnston & Murphy Collection - Jenson Plain Toe. Color Gray Italian Suede. Low Stock. On sale for $256.65. MSRP $295.00.. 4.3 out of 5 stars

Low Stock

Johnston & Murphy Collection Jenson Plain Toe

Johnston & Murphy Collection Jenson Plain Toe

Brand Name: Johnston & Murphy Collection
Product Name: Jenson Plain Toe
Gender: Men's
Color: Gray Italian Suede
Price: $256.65MSRP: $295.00

Allen Edmonds - Randolph Kilty. Color Mahogany. Low Stock. On sale for $288.35. MSRP $395.00.. 4.4 out of 5 stars

Low Stock

Allen Edmonds Randolph Kilty

Allen Edmonds Randolph Kilty

Brand Name: Allen Edmonds
Product Name: Randolph Kilty
Gender: Men's
Color: Mahogany
Price: $288.35MSRP: $395.00

La Canadienne - Lorne. Color Biscotti Suede. Low Stock. On sale for $127.50. MSRP $425.00..

Low Stock

La Canadienne Lorne

La Canadienne Lorne

Brand Name: La Canadienne
Product Name: Lorne
Gender: Men's
Color: Biscotti Suede
Price: $127.50MSRP: $425.00

Massimo Matteo - Ponte Veccio Double Monk Strap. Color Black. Low Stock. On sale for $124.74. MSRP $189.00..

Low Stock

Massimo Matteo Ponte Veccio Double Monk Strap

Massimo Matteo Ponte Veccio Double Monk Strap

Brand Name: Massimo Matteo
Product Name: Ponte Veccio Double Monk Strap
Gender: Men's
Color: Black
Price: $124.74MSRP: $189.00

Frye - Carter Oxford. Color Black. On sale for $313.15. MSRP $348.00..

Frye Carter Oxford

Frye Carter Oxford

Brand Name: Frye
Product Name: Carter Oxford
Gender: Men's
Color: Black
Price: $313.15MSRP: $348.00

Marc Joseph New York - Charles Street. Color Black Testone. Low Stock. On sale for $131.25. MSRP $175.00..

Low Stock

Marc Joseph New York Charles Street

Marc Joseph New York Charles Street

Brand Name: Marc Joseph New York
Product Name: Charles Street
Gender: Men's
Color: Black Testone
Price: $131.25MSRP: $175.00

Marc Joseph New York - Harman ST. Color Havana Grainy. On sale for $78.75. MSRP $175.00..

Marc Joseph New York Harman ST

Marc Joseph New York Harman ST

Brand Name: Marc Joseph New York
Product Name: Harman ST
Gender: Men's
Color: Havana Grainy
Price: $78.75MSRP: $175.00

Marc Joseph New York - Fremont Ave. Color Tan Florence. Low Stock. On sale for $124.80. MSRP $195.00..

Low Stock

Marc Joseph New York Fremont Ave

Marc Joseph New York Fremont Ave

Brand Name: Marc Joseph New York
Product Name: Fremont Ave
Gender: Men's
Color: Tan Florence
Price: $124.80MSRP: $195.00

Marc Joseph New York - Smith ST. Color Havana Grainy/Suede. Low Stock. On sale for $118.95. MSRP $195.00..

Low Stock

Marc Joseph New York Smith ST

Marc Joseph New York Smith ST

Brand Name: Marc Joseph New York
Product Name: Smith ST
Gender: Men's
Color: Havana Grainy/Suede
Price: $118.95MSRP: $195.00

Johnston & Murphy Collection - Hartley Plane Toe. Color Grey. Low Stock. On sale for $169.99. MSRP $295.00..

Low Stock

Johnston & Murphy Collection Hartley Plane Toe

Johnston & Murphy Collection Hartley Plane Toe

Brand Name: Johnston & Murphy Collection
Product Name: Hartley Plane Toe
Gender: Men's
Color: Grey
Price: $169.99MSRP: $295.00

Florsheim - Sorrento Cap Toe Oxford. Color Navy Smooth. Low Stock. On sale for $117.00. MSRP $130.00.. 4.6 out of 5 stars

Low Stock

Florsheim Sorrento Cap Toe Oxford

Florsheim Sorrento Cap Toe Oxford

Brand Name: Florsheim
Product Name: Sorrento Cap Toe Oxford
Gender: Men's
Color: Navy Smooth
Price: $117.00MSRP: $130.00

Massimo Matteo - Slip-On with Buckle. Color Black. Low Stock. On sale for $116.10. MSRP $129.00..

Low Stock

Massimo Matteo Slip-On with Buckle

Massimo Matteo Slip-On with Buckle

Brand Name: Massimo Matteo
Product Name: Slip-On with Buckle
Gender: Men's
Color: Black
Price: $116.10MSRP: $129.00

Massimo Matteo - Stitched Penny Loafers. Color Black. Low Stock. On sale for $112.45. MSRP $124.95..

Low Stock

Massimo Matteo Stitched Penny Loafers

Massimo Matteo Stitched Penny Loafers

Brand Name: Massimo Matteo
Product Name: Stitched Penny Loafers
Gender: Men's
Color: Black
Price: $112.45MSRP: $124.95

TOMS - Navi Oxford. Color Forged Iron. On sale for $56.63. MSRP $89.95.. 3.9 out of 5 stars

TOMS Navi Oxford

TOMS Navi Oxford

Brand Name: TOMS
Product Name: Navi Oxford
Gender: Men's
Color: Forged Iron
Price: $56.63MSRP: $89.95

PIKOLINOS - York M2M-4178. Color Black. Low Stock. On sale for $179.95. MSRP $199.95.. 5.0 out of 5 stars

Low Stock

PIKOLINOS York M2M-4178

PIKOLINOS York M2M-4178

Brand Name: PIKOLINOS
Product Name: York M2M-4178
Gender: Men's
Color: Black
Price: $179.95MSRP: $199.95

PIKOLINOS - York M2M-4178. Color Cuero. Low Stock. On sale for $179.95. MSRP $199.95.. 5.0 out of 5 stars

Low Stock

PIKOLINOS York M2M-4178

PIKOLINOS York M2M-4178

Brand Name: PIKOLINOS
Product Name: York M2M-4178
Gender: Men's
Color: Cuero
Price: $179.95MSRP: $199.95

Marc Joseph New York - Dover ST. Color Black Grainy. Low Stock. On sale for $163.80. MSRP $195.00.. 3.0 out of 5 stars

Low Stock

Marc Joseph New York Dover ST

Marc Joseph New York Dover ST

Brand Name: Marc Joseph New York
Product Name: Dover ST
Gender: Men's
Color: Black Grainy
Price: $163.80MSRP: $195.00

Marc Joseph New York - Dover ST. Color Cognac Grainy. Low Stock. On sale for $124.80. MSRP $195.00.. 3.0 out of 5 stars

Low Stock

Marc Joseph New York Dover ST

Marc Joseph New York Dover ST

Brand Name: Marc Joseph New York
Product Name: Dover ST
Gender: Men's
Color: Cognac Grainy
Price: $124.80MSRP: $195.00

Marc Joseph New York - Clayton RD. Color Cognac Napa Soft. Low Stock. On sale for $117.25. MSRP $175.00..

Low Stock

Marc Joseph New York Clayton RD

Marc Joseph New York Clayton RD

Brand Name: Marc Joseph New York
Product Name: Clayton RD
Gender: Men's
Color: Cognac Napa Soft
Price: $117.25MSRP: $175.00

Marc Joseph New York - Union Street 2. Color Wine Burnished Napa. Low Stock. On sale for $93.00. MSRP $155.00.. 4.8 out of 5 stars

Low Stock

Marc Joseph New York Union Street 2

Marc Joseph New York Union Street 2

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Wine Burnished Napa
Price: $93.00MSRP: $155.00

ECCO - Citytray Apron Toe Tie. Color Black. Low Stock. On sale for $180.00. MSRP $200.00.. 1.0 out of 5 stars

Low Stock

ECCO Citytray Apron Toe Tie

ECCO Citytray Apron Toe Tie

Brand Name: ECCO
Product Name: Citytray Apron Toe Tie
Gender: Men's
Color: Black
Price: $180.00MSRP: $200.00

Martin Dingman - Cambridge. Color Whiskey. Low Stock. On sale for $253.50. MSRP $325.00..

Low Stock

Martin Dingman Cambridge

Martin Dingman Cambridge

Brand Name: Martin Dingman
Product Name: Cambridge
Gender: Men's
Color: Whiskey
Price: $253.50MSRP: $325.00