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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Stretch Chelsea Boots

15 items found

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Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. Low Stock. On sale for $34.50. MSRP $115.00. 70% off. 4.2 out of 5 stars

Low Stock

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: $34.50MSRP: $115

Marc Joseph New York - Austin. Color Truffle Washed Grainy. Low Stock. On sale for $58.50. MSRP $195.00. 70% off. 4.1 out of 5 stars

Low Stock

Marc Joseph New York Austin

Marc Joseph New York Austin

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Truffle Washed Grainy
Price: $58.50MSRP: $195

Birkenstock - Highwood Deep Blue. Color Black. On sale for $136.50. MSRP $210.00. 35% off. 4.2 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Black
Price: $136.50MSRP: $210

Eastland 1955 Edition - Herman. Color Brown. Low Stock. On sale for $79.97. MSRP $135.00. 41% off.

Low Stock

Eastland 1955 Edition Herman

Eastland 1955 Edition Herman

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Brown
Price: $79.97MSRP: $135

Merrell - Moab Adventure 3 Chelsea Wp. Color Black. On sale for $126.99. MSRP $170.00. 25% off. 2.9 out of 5 stars

Merrell Moab Adventure 3 Chelsea Wp

Merrell Moab Adventure 3 Chelsea Wp

Brand Name: Merrell
Product Name: Moab Adventure 3 Chelsea Wp
Gender: Men's
Color: Black
Price: $126.99MSRP: $170

Blundstone - BL558 Classic 550 Chelsea Boot. Color Black. Low Stock. On sale for $134.00. MSRP $209.95. 36% off. 4.5 out of 5 stars

Low Stock

Blundstone BL558 Classic 550 Chelsea Boot

Blundstone BL558 Classic 550 Chelsea Boot

Brand Name: Blundstone
Product Name: BL558 Classic 550 Chelsea Boot
Gender: Unisex
Color: Black
Price: $134MSRP: $209.95

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Cognac. Low Stock. On sale for $107.68. MSRP $145.00. 26% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Maury Cap Toe Chelsea Boot

Stacy Adams Maury Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Cognac
Price: $107.68MSRP: $145

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. Low Stock. On sale for $97.50. MSRP $145.00. 33% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Maury Cap Toe Chelsea Boot

Stacy Adams Maury Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Chocolate
Price: $97.50MSRP: $145

Deer Stags - Argos. Color Black/Blue. On sale for $48.00. MSRP $100.00. 52% off. 3.7 out of 5 stars

Deer Stags Argos

Deer Stags Argos

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Black/Blue
Price: $48MSRP: $100

Eastland 1955 Edition - Herman. Color Black. Low Stock. On sale for $59.97. MSRP $135.00. 56% off.

Low Stock

Eastland 1955 Edition Herman

Eastland 1955 Edition Herman

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Black
Price: $59.97MSRP: $135

Steve Madden - Noah. Color Taupe Suede. Low Stock. On sale for $43.99. MSRP $79.99. 45% off. 4.3 out of 5 stars

Low Stock

Steve Madden Noah

Brand Name: Steve Madden
Product Name: Noah
Gender: Men's
Color: Taupe Suede
Price: $43.99MSRP: $79.99

Birkenstock - Highwood Deep Blue. Color Graphite. On sale for $140.00. MSRP $200.00. 30% off. 4.2 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Graphite
Price: $140MSRP: $200

Stacy Adams - Finney Cap Toe Chelsea Boot. Color Navy Multi. Low Stock. On sale for $128.33. MSRP $160.00. 20% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Finney Cap Toe Chelsea Boot

Stacy Adams Finney Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Finney Cap Toe Chelsea Boot
Gender: Men's
Color: Navy Multi
Price: $128.33MSRP: $160

Birkenstock - Highwood Deep Blue. Color Chocolate. On sale for $157.50. MSRP $210.00. 25% off. 4.2 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Chocolate
Price: $157.50MSRP: $210

Birkenstock - Highwood Deep Blue. Color Dark Tea. On sale for $136.50. MSRP $210.00. 35% off. 4.2 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Dark Tea
Price: $136.50MSRP: $210