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Boots on Sale $50 & Under

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Men's Size 9.5 Dress Comfort Shoes

51 items found

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TOMS - Navi Oxford Dress Casual. Color Oatmeal Heavy Twill/Suede. On sale for $29.98. MSRP $99.95. 70% off. 4.6 out of 5 stars

TOMS Navi Oxford Dress Casual

TOMS Navi Oxford Dress Casual

Brand Name: TOMS
Product Name: Navi Oxford Dress Casual
Gender: Men's
Color: Oatmeal Heavy Twill/Suede
Price: $29.98MSRP: $99.95

TOMS - Navi Oxford Dress Casual. Color Pavement Grey Heavy Twill/Suede. Low Stock. On sale for $29.25. MSRP $99.95. 71% off. 4.6 out of 5 stars

Low Stock

TOMS Navi Oxford Dress Casual

TOMS Navi Oxford Dress Casual

Brand Name: TOMS
Product Name: Navi Oxford Dress Casual
Gender: Men's
Color: Pavement Grey Heavy Twill/Suede
Price: $29.25MSRP: $99.95

Kenneth Cole - Frank. Color Black Leather. On sale for $132.14. MSRP $184.95. 29% off.

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Black Leather
Price: $132.14MSRP: $184.95

Dockers - Elmer. Color Chestnut. On sale for $45.00. MSRP $90.00. 50% off. 3.0 out of 5 stars

Dockers Elmer

Dockers Elmer

Brand Name: Dockers
Product Name: Elmer
Gender: Men's
Color: Chestnut
Price: $45MSRP: $90

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

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

ECCO - Classic Moc 2.0 Slip-On. Color Coffee. Low Stock. On sale for $89.97. MSRP $99.95. 10% off. 3.8 out of 5 stars

Low Stock

ECCO Classic Moc 2.0 Slip-On

ECCO Classic Moc 2.0 Slip-On

Brand Name: ECCO
Product Name: Classic Moc 2.0 Slip-On
Gender: Men's
Color: Coffee
Price: $89.97MSRP: $99.95

Kenneth Cole - Mike. Color Black. On sale for $89.05. MSRP $98.95. 10% off. 3.7 out of 5 stars

Kenneth Cole Mike

Kenneth Cole Mike

Brand Name: Kenneth Cole
Product Name: Mike
Gender: Men's
Color: Black
Price: $89.05MSRP: $98.95

Cole Haan - Bedford Plain-Toe Oxford. Color British Tan. On sale for $97.80. MSRP $120.00. 19% 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: $97.80MSRP: $120

Cole Haan - Grand Remix Apron Toe Oxfords. Color Black. On sale for $126.00. MSRP $140.00. 10% off. 4.0 out of 5 stars

Cole Haan Grand Remix Apron Toe Oxfords

Cole Haan Grand Remix Apron Toe Oxfords

Brand Name: Cole Haan
Product Name: Grand Remix Apron Toe Oxfords
Gender: Men's
Color: Black
Price: $126MSRP: $140

Dockers - Elmer. Color Cognac. On sale for $45.00. MSRP $90.00. 50% off. 3.0 out of 5 stars

Dockers Elmer

Dockers Elmer

Brand Name: Dockers
Product Name: Elmer
Gender: Men's
Color: Cognac
Price: $45MSRP: $90

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 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

Clarks - Steadwell Mid. Color Black Leather. Low Stock. On sale for $99.00. MSRP $110.00. 10% off.

Low Stock

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $99MSRP: $110

Kenneth Cole - Paco. Color Dark Red Leather. On sale for $97.43. MSRP $149.95. 35% off.

Kenneth Cole Paco

Kenneth Cole Paco

Brand Name: Kenneth Cole
Product Name: Paco
Gender: Men's
Color: Dark Red Leather
Price: $97.43MSRP: $149.95

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

Deer Stags - Bangor. Color Black/Black. On sale for $63.00. MSRP $90.00. 30% off. 3.9 out of 5 stars

Deer Stags Bangor

Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $63MSRP: $90

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $49.50. MSRP $90.00. 45% off. 3.9 out of 5 stars

Deer Stags Bangor

Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $49.50MSRP: $90

Kenneth Cole - Tully Cap Toe Oxford. Color Dark Grey Leather. On sale for $111.96. MSRP $159.95. 30% off. 3.0 out of 5 stars

Kenneth Cole Tully Cap Toe Oxford

Kenneth Cole Tully Cap Toe Oxford

Brand Name: Kenneth Cole
Product Name: Tully Cap Toe Oxford
Gender: Men's
Color: Dark Grey Leather
Price: $111.96MSRP: $159.95

Kenneth Cole - Paco. Color Black Leather. On sale for $106.00. MSRP $149.95. 29% off.

Kenneth Cole Paco

Kenneth Cole Paco

Brand Name: Kenneth Cole
Product Name: Paco
Gender: Men's
Color: Black Leather
Price: $106MSRP: $149.95

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

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $135.04. MSRP $194.95. 31% off. 4.0 out of 5 stars

ECCO Metropole Milan Chukka Boots

ECCO Metropole Milan Chukka Boots

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $135.04MSRP: $194.95

Kenneth Cole - Stan. Color Black. On sale for $71.51. MSRP $98.95. 28% off.

Kenneth Cole Stan

Kenneth Cole Stan

Brand Name: Kenneth Cole
Product Name: Stan
Gender: Men's
Color: Black
Price: $71.51MSRP: $98.95

Kenneth Cole - Stan. Color Cognac. On sale for $66.76. MSRP $98.95. 33% off.

Kenneth Cole Stan

Kenneth Cole Stan

Brand Name: Kenneth Cole
Product Name: Stan
Gender: Men's
Color: Cognac
Price: $66.76MSRP: $98.95

Kenneth Cole - Estate Belt Oxford. Color Dark Grey. On sale for $68.12. MSRP $108.95. 37% off. 5.0 out of 5 stars

Kenneth Cole Estate Belt Oxford

Kenneth Cole Estate Belt Oxford

Brand Name: Kenneth Cole
Product Name: Estate Belt Oxford
Gender: Men's
Color: Dark Grey
Price: $68.12MSRP: $108.95

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 - Theme Bit Detail Driver. Color Black. On sale for $97.22. MSRP $144.95. 33% off.

Kenneth Cole Theme Bit Detail Driver

Kenneth Cole Theme Bit Detail Driver

Brand Name: Kenneth Cole
Product Name: Theme Bit Detail Driver
Gender: Men's
Color: Black
Price: $97.22MSRP: $144.95

Kenneth Cole - Theme Bit Detail Driver. Color Cognac. On sale for $108.71. MSRP $144.95. 25% off.

Kenneth Cole Theme Bit Detail Driver

Kenneth Cole Theme Bit Detail Driver

Brand Name: Kenneth Cole
Product Name: Theme Bit Detail Driver
Gender: Men's
Color: Cognac
Price: $108.71MSRP: $144.95

Born - Ryker. Color Brown (Wood). On sale for $90.00. MSRP $150.00. 40% off. 1.0 out of 5 stars

Born Ryker

Born Ryker

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Brown (Wood)
Price: $90MSRP: $150

Calvin Klein - Fasa. Color Black Patent. On sale for $74.80. MSRP $110.00. 32% off.

Calvin Klein Fasa

Calvin Klein Fasa

Brand Name: Calvin Klein
Product Name: Fasa
Gender: Men's
Color: Black Patent
Price: $74.80MSRP: $110

Johnston & Murphy - Jenson Longwing. Color Tan Italian Calfskin. Low Stock. On sale for $250.75. MSRP $295.00. 15% off. 4.1 out of 5 stars

Low Stock

Johnston & Murphy Jenson Longwing

Johnston & Murphy Jenson Longwing

Brand Name: Johnston & Murphy
Product Name: Jenson Longwing
Gender: Men's
Color: Tan Italian Calfskin
Price: $250.75MSRP: $295

Nunn Bush - Chase Moccasin Toe Slip-On Lightweight Contemporary Loafer. Color Navy Multi. Low Stock. On sale for $67.50. MSRP $90.00. 25% off. 4.5 out of 5 stars

Low Stock

Nunn Bush Chase Moccasin Toe Slip-On Lightweight Contemporary Loafer

Nunn Bush Chase Moccasin Toe Slip-On Lightweight Contemporary Loafer

Brand Name: Nunn Bush
Product Name: Chase Moccasin Toe Slip-On Lightweight Contemporary Loafer
Gender: Men's
Color: Navy Multi
Price: $67.50MSRP: $90

Cole Haan - Originalgrand Cityspectre Wholecut Oxfords. Color Dark Chocolate/Dark Natural/Silver Birch. On sale for $133.00. MSRP $190.00. 30% off.

Cole Haan Originalgrand Cityspectre Wholecut Oxfords

Cole Haan Originalgrand Cityspectre Wholecut Oxfords

Brand Name: Cole Haan
Product Name: Originalgrand Cityspectre Wholecut Oxfords
Gender: Men's
Color: Dark Chocolate/Dark Natural/Silver Birch
Price: $133MSRP: $190

Cole Haan - Originalgrand Cityspectre Wholecut Oxfords. Color Truffle Nubuck/Dark Natural/Angora. On sale for $133.00. MSRP $190.00. 30% off.

Cole Haan Originalgrand Cityspectre Wholecut Oxfords

Cole Haan Originalgrand Cityspectre Wholecut Oxfords

Brand Name: Cole Haan
Product Name: Originalgrand Cityspectre Wholecut Oxfords
Gender: Men's
Color: Truffle Nubuck/Dark Natural/Angora
Price: $133MSRP: $190

Cole Haan - Zerogrand Remastered Wing Tip Oxford Unlined. Color Dark Chocolate/Irish Coffee. On sale for $175.57. MSRP $220.00. 20% off. 4.1 out of 5 stars

Cole Haan Zerogrand Remastered Wing Tip Oxford Unlined

Cole Haan Zerogrand Remastered Wing Tip Oxford Unlined

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Wing Tip Oxford Unlined
Gender: Men's
Color: Dark Chocolate/Irish Coffee
Price: $175.57MSRP: $220

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $102.69. MSRP $115.00. 11% off. 4.2 out of 5 stars

Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $102.69MSRP: $115

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

Frye - Barrett Lace Up. Color Cognac. On sale for $173.60. MSRP $248.00. 30% off. 5.0 out of 5 stars

Frye Barrett Lace Up

Frye Barrett Lace Up

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Cognac
Price: $173.60MSRP: $248

Frye - Barrett Lace Up. Color Black. On sale for $223.20. MSRP $248.00. 10% off. 5.0 out of 5 stars

Frye Barrett Lace Up

Frye Barrett Lace Up

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Black
Price: $223.20MSRP: $248

Calvin Klein - Fayze. Color Black Patent. Low Stock. On sale for $71.94. MSRP $115.00. 37% off. 5.0 out of 5 stars

Low Stock

Calvin Klein Fayze

Calvin Klein Fayze

Brand Name: Calvin Klein
Product Name: Fayze
Gender: Men's
Color: Black Patent
Price: $71.94MSRP: $115

Nunn Bush - Centro Flex Wing Tip Oxford. Color Brown Crazy Horse. On sale for $83.39. MSRP $110.00. 24% off. 4.3 out of 5 stars

Nunn Bush Centro Flex Wing Tip Oxford

Nunn Bush Centro Flex Wing Tip Oxford

Brand Name: Nunn Bush
Product Name: Centro Flex Wing Tip Oxford
Gender: Men's
Color: Brown Crazy Horse
Price: $83.39MSRP: $110

Cole Haan - Judson Grand Wingtip Oxfords. Color Raven Suede/Dark Natural. On sale for $172.82. 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: $172.82MSRP: $225

Cole Haan - Judson Grand Wingtip Oxfords. Color Black Scotch Grain/Black. On sale for $172.78. 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: $172.78MSRP: $225

Calvin Klein - Obexx. Color Black Leather. On sale for $84.00. MSRP $140.00. 40% off.

Calvin Klein Obexx

Calvin Klein Obexx

Brand Name: Calvin Klein
Product Name: Obexx
Gender: Men's
Color: Black Leather
Price: $84MSRP: $140

Johnston & Murphy - Flynch Braided Strap Loafer. Color Black Italian Calfskin. On sale for $278.80. MSRP $328.00. 15% off.

Johnston & Murphy Flynch Braided Strap Loafer

Johnston & Murphy Flynch Braided Strap Loafer

Brand Name: Johnston & Murphy
Product Name: Flynch Braided Strap Loafer
Gender: Men's
Color: Black Italian Calfskin
Price: $278.80MSRP: $328

Stacy Adams - Corvell Slip-On Driver Loafer. Color Black. Low Stock. On sale for $45.00. MSRP $90.00. 50% off. 2.0 out of 5 stars

Low Stock

Stacy Adams Corvell Slip-On Driver Loafer

Stacy Adams Corvell Slip-On Driver Loafer

Brand Name: Stacy Adams
Product Name: Corvell Slip-On Driver Loafer
Gender: Men's
Color: Black
Price: $45MSRP: $90

Stacy Adams - Gabardo Bike Toe Lace-Up. Color Blue. On sale for $105.10. MSRP $115.00. 9% off. 4.8 out of 5 stars

Stacy Adams Gabardo Bike Toe Lace-Up

Stacy Adams Gabardo Bike Toe Lace-Up

Brand Name: Stacy Adams
Product Name: Gabardo Bike Toe Lace-Up
Gender: Men's
Color: Blue
Price: $105.10MSRP: $115

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $85.75. MSRP $104.95. 18% off. 4.6 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: $85.75MSRP: $104.95

Stacy Adams - Corvell Slip-On Driver Loafer. Color Navy. Low Stock. On sale for $79.95. MSRP $90.00. 11% off. 2.0 out of 5 stars

Low Stock

Stacy Adams Corvell Slip-On Driver Loafer

Stacy Adams Corvell Slip-On Driver Loafer

Brand Name: Stacy Adams
Product Name: Corvell Slip-On Driver Loafer
Gender: Men's
Color: Navy
Price: $79.95MSRP: $90

Stacy Adams - Prentice Slip-On Loafer. Color White. Low Stock. On sale for $39.00. MSRP $130.00. 70% off. 3.5 out of 5 stars

Low Stock

Stacy Adams Prentice Slip-On Loafer

Stacy Adams Prentice Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Prentice Slip-On Loafer
Gender: Men's
Color: White
Price: $39MSRP: $130