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Boots on Sale $50 & Under

Shop Boots Deals

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Medium Size Slip-On Leather Dress On Sale Products

28 items found

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Bruno Magli - Santino. Color Brown. On sale for $158.00. MSRP $395.00. 60% off. 1.0 out of 5 stars

Bruno Magli Santino

Bruno Magli Santino

Brand Name: Bruno Magli
Product Name: Santino
Gender: Men's
Color: Brown
Price: $158MSRP: $395

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

Kenneth Cole - Theme Bit Detail Driver. Color Black. On sale for $94.25. MSRP $144.95. 35% 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: $94.25MSRP: $144.95

Kenneth Cole - Theme Bit Detail Driver. Color Cognac. On sale for $94.25. MSRP $144.95. 35% 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: $94.25MSRP: $144.95

Johnston & Murphy - Sullivan Bit. Color Black Brush-off Houndstooth Calfskin. On sale for $129.99. MSRP $199.00. 35% off.

Johnston & Murphy Sullivan Bit

Johnston & Murphy Sullivan Bit

Brand Name: Johnston & Murphy
Product Name: Sullivan Bit
Gender: Men's
Color: Black Brush-off Houndstooth Calfskin
Price: $129.99MSRP: $199

Stacy Adams - Aiden Moc Toe Slip-On Loafer. Color Black. Low Stock. On sale for $78.00. MSRP $130.00. 40% off. 4.4 out of 5 stars

Low Stock

Stacy Adams Aiden Moc Toe Slip-On Loafer

Stacy Adams Aiden Moc Toe Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Aiden Moc Toe Slip-On Loafer
Gender: Men's
Color: Black
Price: $78MSRP: $130

Florsheim - Renegade Moc Toe Penny Loafer. Color Cognac Multi. On sale for $108.75. MSRP $145.00. 25% 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: $108.75MSRP: $145

Stacy Adams - Winstead Saddle Slip-On. Color Black. Low Stock. On sale for $108.07. MSRP $125.00. 14% off.

Low Stock

Stacy Adams Winstead Saddle Slip-On

Stacy Adams Winstead Saddle Slip-On

Brand Name: Stacy Adams
Product Name: Winstead Saddle Slip-On
Gender: Men's
Color: Black
Price: $108.07MSRP: $125

Stacy Adams - Marlowe Penny Slip-On Loafer. Color Black Leather. Low Stock. On sale for $93.60. MSRP $114.95. 19% off. 4.6 out of 5 stars

Low Stock

Stacy Adams Marlowe Penny Slip-On Loafer

Stacy Adams Marlowe Penny Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Marlowe Penny Slip-On Loafer
Gender: Men's
Color: Black Leather
Price: $93.60MSRP: $114.95

Kenneth Cole - Paco. Color Black Leather. On sale for $105.00. MSRP $149.95. 30% off.

Kenneth Cole Paco

Kenneth Cole Paco

Brand Name: Kenneth Cole
Product Name: Paco
Gender: Men's
Color: Black Leather
Price: $105MSRP: $149.95

Kenneth Cole - Paco. Color Dark Red Leather. On sale for $105.00. MSRP $149.95. 30% off.

Kenneth Cole Paco

Kenneth Cole Paco

Brand Name: Kenneth Cole
Product Name: Paco
Gender: Men's
Color: Dark Red Leather
Price: $105MSRP: $149.95

Florsheim - Forecast Waterproof Bike Toe Slip-On. Color Cognac Smooth. Low Stock. On sale for $101.50. MSRP $145.00. 30% off. 4.2 out of 5 stars

Low Stock

Florsheim Forecast Waterproof Bike Toe Slip-On

Florsheim Forecast Waterproof Bike Toe Slip-On

Brand Name: Florsheim
Product Name: Forecast Waterproof Bike Toe Slip-On
Gender: Men's
Color: Cognac Smooth
Price: $101.50MSRP: $145

Frye - Hauser Roper. Color Saddle/Dark Brown. Low Stock. On sale for $149.00. MSRP $298.00. 50% off. 3.0 out of 5 stars

Low Stock

Frye Hauser Roper

Frye Hauser Roper

Brand Name: Frye
Product Name: Hauser Roper
Gender: Men's
Color: Saddle/Dark Brown
Price: $149MSRP: $298

Frye - Hauser Roper. Color Tan/Faded Denim. On sale for $149.00. MSRP $298.00. 50% off. 3.0 out of 5 stars

Frye Hauser Roper

Frye Hauser Roper

Brand Name: Frye
Product Name: Hauser Roper
Gender: Men's
Color: Tan/Faded Denim
Price: $149MSRP: $298

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

Stacy Adams - Corvell Slip-On Driver Loafer. Color Tan. Low Stock. On sale for $59.67. MSRP $90.00. 34% 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: Tan
Price: $59.67MSRP: $90

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $31.48. MSRP $104.95. 70% 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: $31.48MSRP: $104.95

Stacy Adams - Paragon Suede Slip On Loafer. Color Navy Suede. Low Stock. On sale for $31.48. MSRP $104.95. 70% off. 4.8 out of 5 stars

Low Stock

Stacy Adams Paragon Suede Slip On Loafer

Stacy Adams Paragon Suede Slip On Loafer

Brand Name: Stacy Adams
Product Name: Paragon Suede Slip On Loafer
Gender: Men's
Color: Navy Suede
Price: $31.48MSRP: $104.95

Stacy Adams - Prentice Slip-On Loafer. Color Black. Low Stock. On sale for $93.85. MSRP $130.00. 28% 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: Black
Price: $93.85MSRP: $130

Stacy Adams - Starleigh Rhinestone Slip-On. Color Black/Silver. On sale for $69.97. MSRP $90.00. 22% off. 4.5 out of 5 stars

Stacy Adams Starleigh Rhinestone Slip-On

Stacy Adams Starleigh Rhinestone Slip-On

Brand Name: Stacy Adams
Product Name: Starleigh Rhinestone Slip-On
Gender: Men's
Color: Black/Silver
Price: $69.97MSRP: $90

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Black Tumbled. 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: Black Tumbled
Price: $34.50MSRP: $115

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. Low Stock. On sale for $69.00. MSRP $115.00. 40% 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: $69MSRP: $115

Kenneth Cole - Frank. Color Black Leather. Low Stock. On sale for $139.42. MSRP $184.95. 25% off.

Low Stock

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Black Leather
Price: $139.42MSRP: $184.95

Stacy Adams - Starleigh Rhinestone Slip-On. Color Black/Gold. On sale for $69.97. MSRP $90.00. 22% off. 4.5 out of 5 stars

Stacy Adams Starleigh Rhinestone Slip-On

Stacy Adams Starleigh Rhinestone Slip-On

Brand Name: Stacy Adams
Product Name: Starleigh Rhinestone Slip-On
Gender: Men's
Color: Black/Gold
Price: $69.97MSRP: $90

Stacy Adams - Starleigh Rhinestone Slip-On. Color Black. Low Stock. On sale for $69.97. MSRP $90.00. 22% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Starleigh Rhinestone Slip-On

Stacy Adams Starleigh Rhinestone Slip-On

Brand Name: Stacy Adams
Product Name: Starleigh Rhinestone Slip-On
Gender: Men's
Color: Black
Price: $69.97MSRP: $90

Stacy Adams - Corvell Slip-On Driver Loafer. Color Navy. Low Stock. On sale for $76.54. MSRP $90.00. 15% 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: $76.54MSRP: $90

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

Johnston & Murphy - Harrison Bit. Color Taupe Suede. On sale for $119.99. MSRP $175.00. 31% off.

Johnston & Murphy Harrison Bit

Johnston & Murphy Harrison Bit

Brand Name: Johnston & Murphy
Product Name: Harrison Bit
Gender: Men's
Color: Taupe Suede
Price: $119.99MSRP: $175