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    Penny Loafer Ankle Boots

    Penny Loafer Ankle Boots

    Men's Thom Browne Penny Loafer Ankle Boots - Black - Casual boots 100% Calfskin Leather, 100% Rubber. Made in Italy. more

    $1,229.00 $707.90

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    Ronny Penny Loafer

    Ronny Penny Loafer

    Men's To Boot New York Ronny Penny Loafer - Black - Loafers A traditional penny keeper and moc toe lend timeless sophistication to a supple suede loafer grounded by a cushioned footbed for long-lasting wear. Cushioned footbed with arch support Leather... more

    $450.00

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    Best Seller
    Tesoro Penny Loafer

    Tesoro Penny Loafer

    Men's To Boot New York Tesoro Penny Loafer - Brown - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

    $399.00

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    American Eagle Outfitters Shoes | American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 | Color: Gray | Size: 8

    American Eagle Outfitters Shoes | American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 | Color: Gray | Size: 8

    American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 Gently Used more

    $25.00

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    J. Crew Shoes | J Crew Superior Boots & Shoes Ludlow Penny Loafers Men's Size 11 D Brown | Color: Brown | Size: 11

    J. Crew Shoes | J Crew Superior Boots & Shoes Ludlow Penny Loafers Men's Size 11 D Brown | Color: Brown | Size: 11

    J Crew Superior Boots & Shoes Ludlow Penny Loafers Men's Size 11 D Brown Size: 11 D Color: Brown Upper Material: Leather Condition: Has Some Wear At The Toe Area more

    $65.00

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    Anthropologie Shoes | Anthropologie Lucky Penny Navy Leather And Suede Ankle Boots | Color: Blue/Red | Size: 8

    Anthropologie Shoes | Anthropologie Lucky Penny Navy Leather And Suede Ankle Boots | Color: Blue/Red | Size: 8

    The Cutest Navy Heel Booties With Argyle Red/Blue Laces - Super Adorable And Unique. Size: 8 Euc. Really Great Condition. Some Minor Wear On Toes. Please See Pics. Soles Look Great! Color: Navy Blue With Red/Blue Laces Side Zip For Easy On Round Toe 3... more

    $50.00

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    Ravello Penny Loafer - Brown - To Boot New York Slip-Ons

    Ravello Penny Loafer - Brown - To Boot New York Slip-Ons

    Men's To Boot New York Ravello Penny Loafer - Brown - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... more

    $399.00

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    Ravello Penny Loafer

    Ravello Penny Loafer

    Men's To Boot New York Ravello Penny Loafer - Black - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... more

    $399.00

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    Ravello Penny Loafer

    Ravello Penny Loafer

    Men's To Boot New York Ravello Penny Loafer - Brown - Loafers A classic penny keeper and moc toe lend sophisticated charm to a burnished leather loafer that will complement your work-to-weekend style. Cushioned footbed with arch support Leather upper,... more

    $399.00

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    Dickerson Penny Loafer

    Dickerson Penny Loafer

    Men's To Boot New York Dickerson Penny Loafer - Black - Loafers A classic penny keeper and sleek leather construction lend timeless sophistication to a polished loafer perfect for any occasion. Leather upper and lining/leather and rubber sole Made in... more

    $425.00

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    Alek Penny Loafer

    Alek Penny Loafer

    Men's To Boot New York Alek Penny Loafer - Brown - Loafers A classic penny strap bridges an Italian-made loafer crafted from soft polished leather with a squared toe and a slightly exaggerated profile. Removable insole Leather upper and... more

    $425.00

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    Reims Penny Loafers

    Reims Penny Loafers

    Men's Paraboot Reims Penny Loafers - Brown 100% Calf Leather. Made in France. more

    $480.91 $415.51

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    Tesoro Penny Loafer

    Tesoro Penny Loafer

    Men's To Boot New York Tesoro Penny Loafer - Gray - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

    $399.00

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    Jaydon Penny Driving Loafer

    Jaydon Penny Driving Loafer

    Men's To Boot New York Jaydon Penny Driving Loafer - Gray - Loafers A classic penny keeper and moc toe add timeless appeal to a leather loafer grounded by a cushioned footbed and segmented driver sole that wraps up the heel. Cushioned footbed with arch... more

    $350.00

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    Ronny Penny Loafer

    Ronny Penny Loafer

    Men's To Boot New York Ronny Penny Loafer - Brown - Loafers A traditional penny keeper and moc toe lend timeless sophistication to a supple suede loafer grounded by a cushioned footbed for long-lasting wear. Cushioned footbed with arch support Leather... more

    $450.00

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    Zenith Penny Loafer

    Zenith Penny Loafer

    Men's To Boot New York Zenith Penny Loafer - Brown - Loafers A woven upper and classic penny keeper create modern dimension on an Italian leather loafer grounded by a cushioned footbed for comfortable wear. Cushioned footbed with arch support Leather... more

    $595.00

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    Tesoro Penny Loafer

    Tesoro Penny Loafer

    Men's To Boot New York Tesoro Penny Loafer - Brown - Loafers Streamlined design showcases the rich leather of a timeless penny loafer built with cushioned arch support and a flexible sole for superior comfort. Cushioned insole with arch support Leather... more

    $399.00

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    Gucci Shoes | Gucci Men's Gg Logo Romance Quebec Loafer Ankle Boots G 12 - Us 12.5 - Eu 46 | Color: Black | Size: 12.5

    Gucci Shoes | Gucci Men's Gg Logo Romance Quebec Loafer Ankle Boots G 12 - Us 12.5 - Eu 46 | Color: Black | Size: 12.5

    Gucci -Condition: Brand New Item With Box + Dust Bag + Card. -All Of Our Items Are 100% Authentic. -Size: Men's Uk 12 - Us 12.5 - Eu 46 (True To Size). -Model: Gg Romance Lace-Up -Code: 663368 -Color: Black. -Gucci Gg Romance Lace-Up Ankle Boots In A... more

    $595.00

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    Anthropologie Shoes | Anthropologie Lucky Penny Buckled Oxford Boots, Sz. 8.5 | Color: Gray | Size: 8.5

    Anthropologie Shoes | Anthropologie Lucky Penny Buckled Oxford Boots, Sz. 8.5 | Color: Gray | Size: 8.5

    These Gorgeous Knee-High Boots By Lucky Penny For Anthropologie Are Made Of Super-Soft Light Grey/Taupe Leather; They Have A Half Zip On The Inside Ankle, A Detachable Fringe Detail At The Ankle/Top Of The Foot, And A 1" Stacked Heel. Very Gently Worn,... more

    $50.00

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    Anthropologie Shoes | Anthropologie Lucky Penny Heeled Boots | Color: Blue/Red | Size: 7.5

    Anthropologie Shoes | Anthropologie Lucky Penny Heeled Boots | Color: Blue/Red | Size: 7.5

    Dark Blue With Red, White And Blue Laces. Leather Upper And Rubber Soles. Some Wear On The Heels As Shown In The Pictures. Medium Width And True To Size. 3" Heels And Inner Ankle Zipper. more

    $28.00

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    Chambers Apron Toe Suede Loafer

    Chambers Apron Toe Suede Loafer

    Men's To Boot New York Chambers Apron Toe Suede Loafer - Blue - Loafers A deconstructed penny strap and squared apron toe distinguish a loafer made of Italian suede with a rubber sole to smartly ground any favorite look. Cushioned insole Leather upper... more

    $399.00

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    Chambers Apron Toe Suede Loafer

    Chambers Apron Toe Suede Loafer

    Men's To Boot New York Chambers Apron Toe Suede Loafer - Brown - Loafers A deconstructed penny strap and squared apron toe distinguish a loafer made of Italian suede with a rubber sole to smartly ground any favorite look. Cushioned insole Leather upper... more

    $399.00

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    Penton Bex Loafer

    Penton Bex Loafer

    Men's Dr. Martens Penton Bex Loafer - Gray - Loafers A classic penny loafer constructed from premium leather offers signature comfort with the brand's AirWair cushioning and a hiking-boot sole. Leather upper/leather and textile lining/synthetic sole... more

    $260.00

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    Free People Shoes | Free People Brady Loafers Pink Brown Suede Leather | Color: Brown/Pink | Size: 39eu

    Free People Shoes | Free People Brady Loafers Pink Brown Suede Leather | Color: Brown/Pink | Size: 39eu

    Free People 39 Ankle Boots Brady Leather Slip On Pink Brown Suede Loafers Shoes Size 39 Style - Ankle Slip On Loafers Suede/Leather Upper Condition: In Good Used Condition. Signs Of Scuffing And Wear On The Suede And Toe/Heel Areas. more

    $45.00

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    Gucci Shoes | Gucci Horsebit Gg Black Velvet Crystal Heel Ankle | Color: Black/Tan | Size: 37.5eu

    Gucci Shoes | Gucci Horsebit Gg Black Velvet Crystal Heel Ankle | Color: Black/Tan | Size: 37.5eu

    Brand-New Designed With The Classic Shape Of The Loafer, The Horsebit Ankle Boot Bridges The Past To The Present. Defined By A Slim Silhouette, Is Presented In Gg Velveta Distinctive Fabric Taken From Gucci Archives. Sparkling Rows Of Crystals... more

    $1,001.00

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    Gucci Shoes | Gucci Mister Gg Monogram Horsebit Velvet Crystal Embellished Boots-Black-Eu 36.5 | Color: Black | Size: 6.5

    Gucci Shoes | Gucci Mister Gg Monogram Horsebit Velvet Crystal Embellished Boots-Black-Eu 36.5 | Color: Black | Size: 6.5

    Gucci Mister Gg Monogram Horsebit Velvet Crystal Embellished Boots-Black-Eu 36.5. ~$1550 Brand New In Box Product Details Style 525242 9jt20 1000 Designed With The Classic Shape Of The Loafer, The Horsebit Ankle Boot Bridges The Past To The Present.... more

    $999.00

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    Mitchum Driving Shoe

    Mitchum Driving Shoe

    Men's To Boot New York Mitchum Driving Shoe - Brown - Loafers Smart suede construction elevates a clean-cut Italian driving shoe topped with a crisp penny strap. Suede upper/leather lining/rubber sole Made in Italy Men's Shoes. more

    $325.00 $195.00

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    Madewell Shoes | Madewell Leather Booties In Cognac | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell Leather Booties In Cognac | Color: Brown/Tan | Size: 8

    Madewell Leather “Brady” Ankle Boots/Loafers In The Cognac Color. Silky-Smooth Leather Features Elastic Stretch Angle And Chunky Heel. Excellent Quality Boot In Like-New Condition Aside From Slight Imperfections On The Right Shoe. Wish They Had Fit Me! more

    $60.00

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    More information about Men's Shoes

    Best prices on Penny loafer ankle boots, Leather in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.