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Boots on Sale $50 & Under

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Size 8.5 Round Toe Comfort Loafers

51 items found

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Nunn Bush - Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On. Color Black. On sale for $59.97. MSRP $100.00. 40% off. 1.5 out of 5 stars

Nunn Bush Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On

Nunn Bush Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On

Brand Name: Nunn Bush
Product Name: Luca Moccasin Toe Penny Loafer Lightweight Comfortable Slip-On
Gender: Men's
Color: Black
Price: $59.97MSRP: $100

Propet - Edsel. Color Black. Low Stock. On sale for $84.95. MSRP $107.49. 21% off. 4.0 out of 5 stars

Low Stock

Propet Edsel

Propet Edsel

Brand Name: Propet
Product Name: Edsel
Gender: Men's
Color: Black
Price: $84.95MSRP: $107.49

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Black Suede. Low Stock. On sale for $34.50. MSRP $115.00. 70% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Ravelle Moc Toe Bit Slip-On

Stacy Adams Ravelle Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Ravelle Moc Toe Bit Slip-On
Gender: Men's
Color: Black Suede
Price: $34.50MSRP: $115

Born - Laken. Color Black. On sale for $90.00. MSRP $100.00. 10% off.

Born Laken

Born Laken

Brand Name: Born
Product Name: Laken
Gender: Men's
Color: Black
Price: $90MSRP: $100

Steve Madden - Kolt. Color Navy Suede. On sale for $49.99. MSRP $120.00. 58% off.

Steve Madden Kolt

Steve Madden Kolt

Brand Name: Steve Madden
Product Name: Kolt
Gender: Men's
Color: Navy Suede
Price: $49.99MSRP: $120

PIKOLINOS - Berna M8J-3150. Color Cuero. Low Stock. On sale for $108.00. MSRP $195.00. 45% off. 4.6 out of 5 stars

Low Stock

PIKOLINOS Berna M8J-3150

PIKOLINOS Berna M8J-3150

Brand Name: PIKOLINOS
Product Name: Berna M8J-3150
Gender: Men's
Color: Cuero
Price: $108MSRP: $195

Rockport - Ellworth. Color Medium Natural Leather. On sale for $97.46. MSRP $129.95. 25% off. 3.0 out of 5 stars

Rockport Ellworth

Rockport Ellworth

Brand Name: Rockport
Product Name: Ellworth
Gender: Men's
Color: Medium Natural Leather
Price: $97.46MSRP: $129.95

Deer Stags - Infinity. Color Brown. On sale for $44.97. MSRP $64.99. 31% off. 4.7 out of 5 stars

Deer Stags Infinity

Deer Stags Infinity

Brand Name: Deer Stags
Product Name: Infinity
Gender: Men's
Color: Brown
Price: $44.97MSRP: $64.99

Bruno Magli - Arlo. Color White. Low Stock. On sale for $217.25. MSRP $395.00. 45% off.

Low Stock

Bruno Magli Arlo

Bruno Magli Arlo

Brand Name: Bruno Magli
Product Name: Arlo
Gender: Men's
Color: White
Price: $217.25MSRP: $395

Eastland 1955 Edition - Baldwin. Color Black. Low Stock. On sale for $50.00. MSRP $125.00. 60% off. 3.0 out of 5 stars

Low Stock

Eastland 1955 Edition Baldwin

Eastland 1955 Edition Baldwin

Brand Name: Eastland 1955 Edition
Product Name: Baldwin
Gender: Men's
Color: Black
Price: $50MSRP: $125

Rockport - Liam. Color Dark Brown Leather. On sale for $64.97. MSRP $129.95. 50% off. 4.3 out of 5 stars

Rockport Liam

Rockport Liam

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Dark Brown Leather
Price: $64.97MSRP: $129.95

Nunn Bush - MAC Moccasin Toe Slip-On. Color Brown. On sale for $76.85. MSRP $100.00. 23% off. 4.4 out of 5 stars

Nunn Bush MAC Moccasin Toe Slip-On

Nunn Bush MAC Moccasin Toe Slip-On

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Slip-On
Gender: Men's
Color: Brown
Price: $76.85MSRP: $100

Born - Laken. Color Dark Brown (Castagno). Low Stock. On sale for $65.00. MSRP $100.00. 35% off.

Low Stock

Born Laken

Born Laken

Brand Name: Born
Product Name: Laken
Gender: Men's
Color: Dark Brown (Castagno)
Price: $65MSRP: $100

Steve Madden - Abott. Color Black. On sale for $113.18. MSRP $130.00. 13% off.

Steve Madden Abott

Steve Madden Abott

Brand Name: Steve Madden
Product Name: Abott
Gender: Men's
Color: Black
Price: $113.18MSRP: $130

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

Johnston & Murphy - Taylor Bit. Color Black Italian Calfskin. On sale for $208.60. MSRP $298.00. 30% off.

Johnston & Murphy Taylor Bit

Johnston & Murphy Taylor Bit

Brand Name: Johnston & Murphy
Product Name: Taylor Bit
Gender: Men's
Color: Black Italian Calfskin
Price: $208.60MSRP: $298

Dr. Scholl's - Feel Engaged. Color Black Leather. Low Stock. On sale for $97.50. MSRP $130.00. 25% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Feel Engaged

Dr. Scholl's Feel Engaged

Brand Name: Dr. Scholl's
Product Name: Feel Engaged
Gender: Men's
Color: Black Leather
Price: $97.50MSRP: $130

Dr. Scholl's - Feel Engaged. Color Dark Tan Leather. On sale for $78.81. MSRP $130.00. 39% off. 5.0 out of 5 stars

Dr. Scholl's Feel Engaged

Dr. Scholl's Feel Engaged

Brand Name: Dr. Scholl's
Product Name: Feel Engaged
Gender: Men's
Color: Dark Tan Leather
Price: $78.81MSRP: $130

Steve Madden - Norphius. Color Taupe Fabric. On sale for $79.95. MSRP $100.00. 20% off.

Steve Madden Norphius

Steve Madden Norphius

Brand Name: Steve Madden
Product Name: Norphius
Gender: Men's
Color: Taupe Fabric
Price: $79.95MSRP: $100

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 - 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

Steve Madden - Colter. Color Navy Suede. On sale for $76.95. MSRP $120.00. 36% off. 4.0 out of 5 stars

Steve Madden Colter

Steve Madden Colter

Brand Name: Steve Madden
Product Name: Colter
Gender: Men's
Color: Navy Suede
Price: $76.95MSRP: $120

Steve Madden - Colter. Color Sand Suede. On sale for $74.18. MSRP $120.00. 38% off. 4.0 out of 5 stars

Steve Madden Colter

Steve Madden Colter

Brand Name: Steve Madden
Product Name: Colter
Gender: Men's
Color: Sand Suede
Price: $74.18MSRP: $120

Steve Madden - Frankk. Color Cognac Suede. On sale for $39.99. MSRP $100.00. 60% off. 5.0 out of 5 stars

Steve Madden Frankk

Steve Madden Frankk

Brand Name: Steve Madden
Product Name: Frankk
Gender: Men's
Color: Cognac Suede
Price: $39.99MSRP: $100

Steve Madden - Gramada. Color Taupe Nubuck. On sale for $111.05. MSRP $130.00. 15% off.

Steve Madden Gramada

Steve Madden Gramada

Brand Name: Steve Madden
Product Name: Gramada
Gender: Men's
Color: Taupe Nubuck
Price: $111.05MSRP: $130

Steve Madden - Abott. Color Taupe Suede. On sale for $109.26. MSRP $130.00. 16% off.

Steve Madden Abott

Steve Madden Abott

Brand Name: Steve Madden
Product Name: Abott
Gender: Men's
Color: Taupe Suede
Price: $109.26MSRP: $130

Johnston & Murphy - Lewis Venetian. Color Tan Full Grain. Low Stock. On sale for $74.50. MSRP $149.00. 50% off. 4.3 out of 5 stars

Low Stock

Johnston & Murphy Lewis Venetian

Johnston & Murphy Lewis Venetian

Brand Name: Johnston & Murphy
Product Name: Lewis Venetian
Gender: Men's
Color: Tan Full Grain
Price: $74.50MSRP: $149

PIKOLINOS - Berna M8J-3150. Color Blue. Low Stock. On sale for $126.75. MSRP $195.00. 35% off. 4.6 out of 5 stars

Low Stock

PIKOLINOS Berna M8J-3150

PIKOLINOS Berna M8J-3150

Brand Name: PIKOLINOS
Product Name: Berna M8J-3150
Gender: Men's
Color: Blue
Price: $126.75MSRP: $195

Stacy Adams - Gill Saddle Slip-On Loafer. Color Mushroom Multi. Low Stock. On sale for $83.24. MSRP $104.95. 21% 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: $83.24MSRP: $104.95

Nunn Bush - Otto EZ Moccasin Toe Slip-On Easy On Loafer. Color Tan. Low Stock. On sale for $71.75. MSRP $90.00. 20% off. 3.5 out of 5 stars

Low Stock

Nunn Bush Otto EZ Moccasin Toe Slip-On Easy On Loafer

Nunn Bush Otto EZ Moccasin Toe Slip-On Easy On Loafer

Brand Name: Nunn Bush
Product Name: Otto EZ Moccasin Toe Slip-On Easy On Loafer
Gender: Men's
Color: Tan
Price: $71.75MSRP: $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

Clarks - Gessler Step. Color Mahogany. On sale for $82.14. MSRP $95.00. 14% off. 3.0 out of 5 stars

Clarks Gessler Step

Clarks Gessler Step

Brand Name: Clarks
Product Name: Gessler Step
Gender: Men's
Color: Mahogany
Price: $82.14MSRP: $95

Deer Stags - Infinity. Color Black. On sale for $54.99. MSRP $64.99. 15% off. 4.7 out of 5 stars

Deer Stags Infinity

Deer Stags Infinity

Brand Name: Deer Stags
Product Name: Infinity
Gender: Men's
Color: Black
Price: $54.99MSRP: $64.99

PIKOLINOS - Avila M1T-3205. Color Cuero. Low Stock. On sale for $146.25. MSRP $195.00. 25% off. 5.0 out of 5 stars

Low Stock

PIKOLINOS Avila M1T-3205

PIKOLINOS Avila M1T-3205

Brand Name: PIKOLINOS
Product Name: Avila M1T-3205
Gender: Men's
Color: Cuero
Price: $146.25MSRP: $195

Florsheim - Motion Moc Toe Slip-On. Color Mushroom Nubuck. Low Stock. On sale for $84.00. MSRP $120.00. 30% off. 4.3 out of 5 stars

Low Stock

Florsheim Motion Moc Toe Slip-On

Florsheim Motion Moc Toe Slip-On

Brand Name: Florsheim
Product Name: Motion Moc Toe Slip-On
Gender: Men's
Color: Mushroom Nubuck
Price: $84MSRP: $120

Samuel Hubbard - Frequent Traveler Loafer. Color Black. $285.00. 4.5 out of 5 stars

Samuel Hubbard Frequent Traveler Loafer

Samuel Hubbard Frequent Traveler Loafer

Brand Name: Samuel Hubbard
Product Name: Frequent Traveler Loafer
Gender: Men's
Color: Black
Price: $285

COACH - Reagan Loafer. Color Black. Low Stock. On sale for $139.00. MSRP $250.00. 44% off. 5.0 out of 5 stars

Low Stock

COACH Reagan Loafer

COACH Reagan Loafer

Brand Name: COACH
Product Name: Reagan Loafer
Gender: Men's
Color: Black
Price: $139MSRP: $250

Cole Haan - Pinch Prep Penny Loafer. Color Birchbeige Suede/Dark Chocolate. On sale for $120.55. 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: $120.55MSRP: $130

Calvin Klein - Ellard. Color Black. On sale for $73.78. MSRP $110.00. 33% off.

Calvin Klein Ellard

Calvin Klein Ellard

Brand Name: Calvin Klein
Product Name: Ellard
Gender: Men's
Color: Black
Price: $73.78MSRP: $110

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Green Suede. Low Stock. On sale for $105.79. MSRP $115.00. 8% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Ravelle Moc Toe Bit Slip-On

Stacy Adams Ravelle Moc Toe Bit Slip-On

Brand Name: Stacy Adams
Product Name: Ravelle Moc Toe Bit Slip-On
Gender: Men's
Color: Green Suede
Price: $105.79MSRP: $115

Eastland 1955 Edition - Scarborough. Color Beige. Low Stock. On sale for $50.00. MSRP $125.00. 60% off. 5.0 out of 5 stars

Low Stock

Eastland 1955 Edition Scarborough

Eastland 1955 Edition Scarborough

Brand Name: Eastland 1955 Edition
Product Name: Scarborough
Gender: Men's
Color: Beige
Price: $50MSRP: $125

Columbia - Landroamer™ Camper. Color Mud/Warp Red. $80.00. 3.9 out of 5 stars

Columbia Landroamer™ Camper

Columbia Landroamer™ Camper

Brand Name: Columbia
Product Name: Landroamer™ Camper
Gender: Men's
Color: Mud/Warp Red
Price: $80

Dunham - Waves. Color Stone Nubuck. $159.95. 3.5 out of 5 stars

Dunham Waves

Dunham Waves

Brand Name: Dunham
Product Name: Waves
Gender: Men's
Color: Stone Nubuck
Price: $159.95

Kenneth Cole - Theo. Color Black. $139.95.

Kenneth Cole Theo

Kenneth Cole Theo

Brand Name: Kenneth Cole
Product Name: Theo
Gender: Men's
Color: Black
Price: $139.95

Kenneth Cole - Theo. Color Cognac. On sale for $125.95. MSRP $139.95. 10% off.

Kenneth Cole Theo

Kenneth Cole Theo

Brand Name: Kenneth Cole
Product Name: Theo
Gender: Men's
Color: Cognac
Price: $125.95MSRP: $139.95

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 $122.77. 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: $122.77MSRP: $170

Cole Haan - Zerogrand Remastered Stitchlite Loafer. Color Sea Stone/Natural/Ivory. On sale for $157.37. 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: $157.37MSRP: $170

Cole Haan - American Classics Bit Loafers. Color Midnight Moon/Oat. On sale for $145.00. 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: $145MSRP: $175

Cole Haan - American Classics Bit Loafers. Color Raven Nubuck/Dark Latte. On sale for $147.05. MSRP $175.00. 16% 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: $147.05MSRP: $175

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