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Boots on Sale $50 & Under

Shop Boots Deals

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Medium Size Leather Loafers

36 items found

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Cole Haan - American Classics Bit Loafers. Color Raven Nubuck/Dark Latte. On sale for $152.87. MSRP $175.00. 13% off. 5.0 out of 5 stars

Cole Haan American Classics Bit Loafers

Cole Haan American Classics Bit Loafers

Brand Name: Cole Haan
Product Name: American Classics Bit Loafers
Gender: Men's
Color: Raven Nubuck/Dark Latte
Price: $152.87MSRP: $175

Cole Haan - Pinch Prep Penny Loafer. Color Dark Chocolate BOX Brush Off/Black. On sale for $119.96. MSRP $140.00. 14% off. 3.9 out of 5 stars

Cole Haan Pinch Prep Penny Loafer

Cole Haan Pinch Prep Penny Loafer

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Dark Chocolate BOX Brush Off/Black
Price: $119.96MSRP: $140

Cole Haan - Pinch Weekender Penny. Color Black/Angora. On sale for $116.47. MSRP $120.00. 3% off. 4.2 out of 5 stars

Cole Haan Pinch Weekender Penny

Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: Black/Angora
Price: $116.47MSRP: $120

Cole Haan - Pinch Weekender Venetians. Color China Blue Suede/Ivory. Low Stock. On sale for $65.00. MSRP $130.00. 50% off.

Low Stock

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: China Blue Suede/Ivory
Price: $65MSRP: $130

Cole Haan - Pinch Weekender Venetians. Color Dark Chocolate/Angora. On sale for $65.00. MSRP $130.00. 50% off.

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: Dark Chocolate/Angora
Price: $65MSRP: $130

Calvin Klein - Crispo. Color Black Leather. Low Stock. On sale for $98.00. MSRP $140.00. 30% off. 3.5 out of 5 stars

Low Stock

Calvin Klein Crispo

Calvin Klein Crispo

Brand Name: Calvin Klein
Product Name: Crispo
Gender: Men's
Color: Black Leather
Price: $98MSRP: $140

Cole Haan - Pinch Prep Penny Loafer. Color Birchbeige Suede/Dark Chocolate. On sale for $120.51. MSRP $130.00. 7% off. 3.9 out of 5 stars

Cole Haan Pinch Prep Penny Loafer

Cole Haan Pinch Prep Penny Loafer

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Birchbeige Suede/Dark Chocolate
Price: $120.51MSRP: $130

Cole Haan - Pinch Weekender Penny. Color British Tan/Angora. Low Stock. On sale for $108.00. MSRP $120.00. 10% off. 4.2 out of 5 stars

Low Stock

Cole Haan Pinch Weekender Penny

Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: British Tan/Angora
Price: $108MSRP: $120

Cole Haan - Harmon Grand Penny Loafers. Color Black Waterproof/Black/Black. Low Stock. On sale for $153.00. MSRP $180.00. 15% off.

Low Stock

Cole Haan Harmon Grand Penny Loafers

Cole Haan Harmon Grand Penny Loafers

Brand Name: Cole Haan
Product Name: Harmon Grand Penny Loafers
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $153MSRP: $180

Cole Haan - Brower Penny Loafers. Color Black/Black. On sale for $149.29. MSRP $160.00. 7% off.

Cole Haan Brower Penny Loafers

Cole Haan Brower Penny Loafers

Brand Name: Cole Haan
Product Name: Brower Penny Loafers
Gender: Men's
Color: Black/Black
Price: $149.29MSRP: $160

Cole Haan - American Classics Casual Loafer. Color Truffle Nubuck/Ivory. Low Stock. On sale for $133.20. MSRP $148.00. 10% off. 5.0 out of 5 stars

Low Stock

Cole Haan American Classics Casual Loafer

Cole Haan American Classics Casual Loafer

Brand Name: Cole Haan
Product Name: American Classics Casual Loafer
Gender: Men's
Color: Truffle Nubuck/Ivory
Price: $133.20MSRP: $148

Cole Haan - American Classics Casual Loafer. Color Midnight Moon Suede/Ivory. On sale for $103.60. MSRP $148.00. 30% off. 5.0 out of 5 stars

Cole Haan American Classics Casual Loafer

Cole Haan American Classics Casual Loafer

Brand Name: Cole Haan
Product Name: American Classics Casual Loafer
Gender: Men's
Color: Midnight Moon Suede/Ivory
Price: $103.60MSRP: $148

Cole Haan - American Classics Casual Loafer. Color Spiced Brown Suede/Ivory. Low Stock. On sale for $111.00. MSRP $148.00. 25% off. 5.0 out of 5 stars

Low Stock

Cole Haan American Classics Casual Loafer

Cole Haan American Classics Casual Loafer

Brand Name: Cole Haan
Product Name: American Classics Casual Loafer
Gender: Men's
Color: Spiced Brown Suede/Ivory
Price: $111MSRP: $148

Cole Haan - Hawthorne Penny Loafer. Color Black. Low Stock. On sale for $133.20. MSRP $148.00. 10% off. 3.7 out of 5 stars

Low Stock

Cole Haan Hawthorne Penny Loafer

Cole Haan Hawthorne Penny Loafer

Brand Name: Cole Haan
Product Name: Hawthorne Penny Loafer
Gender: Men's
Color: Black
Price: $133.20MSRP: $148

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

Cole Haan - Grand 4-Eye Loafers. Color Black Nubuck/Pavement. On sale for $111.95. MSRP $130.00. 14% off.

Cole Haan Grand 4-Eye Loafers

Cole Haan Grand 4-Eye Loafers

Brand Name: Cole Haan
Product Name: Grand 4-Eye Loafers
Gender: Men's
Color: Black Nubuck/Pavement
Price: $111.95MSRP: $130

Calvin Klein - Jay. Color Black 1. On sale for $98.10. MSRP $109.00. 10% off. 5.0 out of 5 stars

Calvin Klein Jay

Calvin Klein Jay

Brand Name: Calvin Klein
Product Name: Jay
Gender: Men's
Color: Black 1
Price: $98.10MSRP: $109

Cole Haan - Grand 4-Eye Loafers. Color Spiced Brown Suede/Silver Birch. On sale for $106.52. MSRP $130.00. 18% off.

Cole Haan Grand 4-Eye Loafers

Cole Haan Grand 4-Eye Loafers

Brand Name: Cole Haan
Product Name: Grand 4-Eye Loafers
Gender: Men's
Color: Spiced Brown Suede/Silver Birch
Price: $106.52MSRP: $130

Cole Haan - Brower Penny Loafers. Color Woodbury/Gum Water Resistant. Low Stock. On sale for $144.00. MSRP $160.00. 10% off.

Low Stock

Cole Haan Brower Penny Loafers

Cole Haan Brower Penny Loafers

Brand Name: Cole Haan
Product Name: Brower Penny Loafers
Gender: Men's
Color: Woodbury/Gum Water Resistant
Price: $144MSRP: $160

Cole Haan - Grand 4-Eye Loafers. Color British Tan/Angora. On sale for $109.63. MSRP $130.00. 16% off.

Cole Haan Grand 4-Eye Loafers

Cole Haan Grand 4-Eye Loafers

Brand Name: Cole Haan
Product Name: Grand 4-Eye Loafers
Gender: Men's
Color: British Tan/Angora
Price: $109.63MSRP: $130

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Sea Stone/Natural/Ivory. On sale for $157.84. MSRP $170.00. 7% off.

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Sea Stone/Natural/Ivory
Price: $157.84MSRP: $170

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Black/Brit Tan/Ivory. On sale for $93.50. MSRP $170.00. 45% off.

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Black/Brit Tan/Ivory
Price: $93.50MSRP: $170

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Navy Blazer/Brit Tan/Ivory. Low Stock. On sale for $122.69. MSRP $170.00. 28% off.

Low Stock

Cole Haan Zerogrand Remastered Stitchlite Loafer

Cole Haan Zerogrand Remastered Stitchlite Loafer

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Stitchlite Loafer
Gender: Men's
Color: Navy Blazer/Brit Tan/Ivory
Price: $122.69MSRP: $170

Cole Haan - Originalgrand Energyweave Venetian Loafers. Color Ironstone Nubuck/Paloma/Paloma. On sale for $137.13. MSRP $160.00. 14% off. 5.0 out of 5 stars

Cole Haan Originalgrand Energyweave Venetian Loafers

Cole Haan Originalgrand Energyweave Venetian Loafers

Brand Name: Cole Haan
Product Name: Originalgrand Energyweave Venetian Loafers
Gender: Men's
Color: Ironstone Nubuck/Paloma/Paloma
Price: $137.13MSRP: $160

Cole Haan - Pinch Weekender Venetians. Color Black/Angora. Low Stock. On sale for $65.00. MSRP $130.00. 50% off.

Low Stock

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: Black/Angora
Price: $65MSRP: $130

Cole Haan - Originalgrand Energyweave Venetian Loafers. Color Navy Blazer/Paloma/Gum. On sale for $130.61. MSRP $160.00. 18% off. 5.0 out of 5 stars

Cole Haan Originalgrand Energyweave Venetian Loafers

Cole Haan Originalgrand Energyweave Venetian Loafers

Brand Name: Cole Haan
Product Name: Originalgrand Energyweave Venetian Loafers
Gender: Men's
Color: Navy Blazer/Paloma/Gum
Price: $130.61MSRP: $160

Cole Haan - Davies Grand Penny Driving Loafers. Color China Blue Suede/Gum. Low Stock. On sale for $75.00. MSRP $150.00. 50% off. 5.0 out of 5 stars

Low Stock

Cole Haan Davies Grand Penny Driving Loafers

Cole Haan Davies Grand Penny Driving Loafers

Brand Name: Cole Haan
Product Name: Davies Grand Penny Driving Loafers
Gender: Men's
Color: China Blue Suede/Gum
Price: $75MSRP: $150

Cole Haan - Originalgrand Energyweave Venetian Loafers. Color New Caramel/Irish Coffee/Truffle. On sale for $144.00. MSRP $160.00. 10% off. 5.0 out of 5 stars

Cole Haan Originalgrand Energyweave Venetian Loafers

Cole Haan Originalgrand Energyweave Venetian Loafers

Brand Name: Cole Haan
Product Name: Originalgrand Energyweave Venetian Loafers
Gender: Men's
Color: New Caramel/Irish Coffee/Truffle
Price: $144MSRP: $160

Cole Haan - Pinch Weekender Venetians. Color British Tan/Angora. Low Stock. On sale for $65.00. MSRP $130.00. 50% off.

Low Stock

Cole Haan Pinch Weekender Venetians

Cole Haan Pinch Weekender Venetians

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: British Tan/Angora
Price: $65MSRP: $130

Calvin Klein - Oliver. Color Light Grey. On sale for $70.05. MSRP $99.00. 29% off. 3.0 out of 5 stars

Calvin Klein Oliver

Calvin Klein Oliver

Brand Name: Calvin Klein
Product Name: Oliver
Gender: Men's
Color: Light Grey
Price: $70.05MSRP: $99

Calvin Klein - Jameson. Color Medium Brown. Low Stock. On sale for $95.24. MSRP $125.00. 24% off. 5.0 out of 5 stars

Low Stock

Calvin Klein Jameson

Calvin Klein Jameson

Brand Name: Calvin Klein
Product Name: Jameson
Gender: Men's
Color: Medium Brown
Price: $95.24MSRP: $125

Calvin Klein - Oliver. Color Black 1. On sale for $69.99. MSRP $105.00. 33% off. 3.0 out of 5 stars

Calvin Klein Oliver

Calvin Klein Oliver

Brand Name: Calvin Klein
Product Name: Oliver
Gender: Men's
Color: Black 1
Price: $69.99MSRP: $105

Cole Haan - American Classics Bit Loafers. Color Dark Chocolate BOX Brush Off/Black. On sale for $156.76. MSRP $175.00. 10% off. 5.0 out of 5 stars

Cole Haan American Classics Bit Loafers

Cole Haan American Classics Bit Loafers

Brand Name: Cole Haan
Product Name: American Classics Bit Loafers
Gender: Men's
Color: Dark Chocolate BOX Brush Off/Black
Price: $156.76MSRP: $175

Cole Haan - American Classics Bit Loafers. Color Midnight Moon/Oat. On sale for $146.07. MSRP $175.00. 17% off. 5.0 out of 5 stars

Cole Haan American Classics Bit Loafers

Cole Haan American Classics Bit Loafers

Brand Name: Cole Haan
Product Name: American Classics Bit Loafers
Gender: Men's
Color: Midnight Moon/Oat
Price: $146.07MSRP: $175

Calvin Klein - Magnus. Color Black/Black/Weave Emboss Action. On sale for $87.10. MSRP $88.99. 2% off. 2.3 out of 5 stars

Calvin Klein Magnus

Calvin Klein Magnus

Brand Name: Calvin Klein
Product Name: Magnus
Gender: Men's
Color: Black/Black/Weave Emboss Action
Price: $87.10MSRP: $88.99

Cole Haan - American Classics Bit Loafers. Color Dark Chocolate Suede/Truffle. On sale for $157.50. MSRP $175.00. 10% off. 5.0 out of 5 stars

Cole Haan American Classics Bit Loafers

Cole Haan American Classics Bit Loafers

Brand Name: Cole Haan
Product Name: American Classics Bit Loafers
Gender: Men's
Color: Dark Chocolate Suede/Truffle
Price: $157.50MSRP: $175