Men's Shoes › uptown penny loafer

L'Asola Suede Penny Loafer

Men's Zegna L'Asola Suede Penny Loafer - Gray - Loafers Named for the buttonholes in finely tailored menswear, this iconic leather loafer from the Italian label features a clean, classic silhouette. Leather upper, lining and sole Made in Italy Men's... more

Morgan Moc Toe Penny Loafer

Men's Gordon Rush Morgan Moc Toe Penny Loafer - Brown - Loafers Fine craftsmanship shines through on this refined penny loafer in Italian leather set on a flexible rubber sole that provides enhanced traction. Removable OrthoLite® insole Leather upper... more

Leather Penny Loafers

Men's Santoni Leather Penny Loafers - Black burgundy calf leather smooth grain almond toe moc stitching penny slot slip-on style stacked sole branded leather insole leather lining Size: 6. Gender: Male. Material:Rubber/Calf Leather/Calf Leather. more

Soft Suede Penny Loafers

Men's John Lobb Soft Suede Penny Loafers - Gray John Lobb loafers in suede/leather and rubber Stacked heel Round moc toe Notched vamp Penny keeper strap Leather lining Non welted Made in Italy more

Suede Driver Penny Loafers

Men's Giorgio Armani Suede Driver Penny Loafers - Green Giorgio Armani driver loafers in soft calf suede Flat heel Round moc toe Notched vamp with keeper strap Slipon style Leather footbed Leather lining Rubber driver outsole Made in Italy more

Gommino Round Toe Penny Loafers

Men's Tod's Gommino Round Toe Penny Loafers - Brown 100% Calf Leather, 100% Rubber, 100% Calf Suede. Made in Italy. more

Alexis Penny Loafer

Men's Mephisto Alexis Penny Loafer - Black - Loafers Breathable comfort and support are the name of the game with this classic penny loafer shaped from smooth leather. Removable, cushioned insole with arch support Leather upper and lining/rubber sole... more

Classic Dan Leather Tassel Penny Loafers

Women's Sebago Classic Dan Leather Tassel Penny Loafers - White Sebago "Dan" made of smooth corrected grain leather to stand the test of time and handsewn with the finest craftsmanship, these 4 seasons slip on beefroll penny loafer mocs come with upper... more

Slip-on Penny Loafers

Men's Santoni Slip-on Penny Loafers - Brown Dimensions: Heel: 3cm, Sole: 1.5cm 100% Calf Leather. Made in Italy. more

Royce Kiltie Brushed Leather Penny Loafers

Men's Stuart Weitzman Royce Kiltie Brushed Leather Penny Loafers - Brown Weitzman "Royce Kiltie" penny loafers in brushed calf leather 0.75 in / 20 mm stacked heel Almond toe Notched vamp Leather outsole Lining: Goat leather Slipon style Made in Italy more

Athens Penny Driving Loafer

Men's Johnston & Murphy Athens Penny Driving Loafer - Green - Loafers Sleek and sporty, this loafer made of Brazilian leather features a classic penny strap and foam cushioning set atop a lugged driver sole that wraps up the heel. Removable memory foam... more

Newman Leather Penny Loafers

Men's Allen Edmonds Newman Leather Penny Loafers - Black Allen Edmonds "Newman" penny loafers in premium calfskin leather with an antique finish Comfortable, handsewn construction 0.50 in / 15 mm stacked heel Round moc toe Penny keeper strap Padded... more

Brown Classic Penny Loafers

Men's Thom Browne Brown Classic Penny Loafers - Black Buffed calfskin loafers in brown. more

Ettore Penny Loafer

Men's Bruno Magli Ettore Penny Loafer - Black - Loafers Step out in classic style with this traditional loafer crafted from smooth Italian leather with a padded sock liner for additional support. Cushioned insole Leather upper and lining/rubber sole... more

Soho Suede Casual Penny Loafers

Women's Stuart Weitzman Soho Suede Casual Penny Loafers - Brown Stuart Weitzman "Soho" suede casual penny loafers 2.36 in / 60 mm chunky heel; 1.25 in / 30 mm platform Round apron toe Notched vamp with keeper strap Slipon style Rubber outsole Lining:... more

Le Loafer Penny Slippers

Men's Saint Laurent Le Loafer Penny Slippers - Black - Loafers Penny loafers with Saint Laurent embossed back tab and saddle decorated with the cassandre on the front. more

Thom E Shearling Penny Loafers

Men's Thom Browne Thom E Shearling Penny Loafers - Black Calfskin suede loafers in black. more

Temple Leather Penny Loafers

Men's Officine Creative Temple Leather Penny Loafers - Brown brown black calf leather polished finish penny slot almond toe branded leather insole flat sole Size: 42 1/2. Gender: Male. Material:Calf Leather/Calf Leather/Calf Leather. more

Berkly Penny Loafer

Men's Dune Berkly Penny Loafer - Brown - Loafers Pull together your look with the effortlessly polished style of this contemporary take on a classic penny loafer. Leather upper/synthetic lining and sole Imported more

Aalto Penny Loafer

Men's ALDO Aalto Penny Loafer - Black - Loafers A herringbone-textured vamp lends a contemporary touch to this leather penny loafer set on a flexible sole. Leather upper/recycled-polyester, textile and synthetic lining/rubber sole Imported more

Penny Loafer Slingback Sandal

Men's Thom Browne Penny Loafer Slingback Sandal - Loafers Thom Browne continues to redefine wardrobe classics with this smooth leather slingback sandal boasting the cutout shell of a traditional penny loafer. Adjustable slingback strap with buckle... more

Leather Penny Loafers

Men's Santoni Leather Penny Loafers - Brown brown leather penny slot round toe branded leather insole flat leather sole Size: 6. Gender: Male. Material:Leather/Leather/Suede. more

Smooth Leather Penny Loafers

Men's Tod's Smooth Leather Penny Loafers - Black Tod's penny loafers in smooth calf leather Stacked heel Round moc toe Penny keeper strap Tongue with stamped monogram Pebbled rubber outsole Slipon style Clean with a soft bristled brush Made in Italy more

Penny Slot Suede Loafers

Men's Kiton Penny Slot Suede Loafers - Gray calf suede rubber sole almond toe penny slot piped-trim detailing embroidered logo to the rear Size: 41. Gender: Male. Material:Rubber/Calf Leather/Calf Suede. more

Woven Suede Penny Loafers

Men's Jo Ghost Woven Suede Penny Loafers - Blue Jo Ghost penny loafers in extremely soft and flexible woven suede and napa leather Stacked heel Round toe Notched vamp Lining: leather Slipon style Made in Italy more

Moca Penny Loafers

Men's Santoni Moca Penny Loafers - Black Highlights. Black. Leather. Almond toe. Leather lining. Branded insole. Low block heel. Made in italy. Composition. Sole: rubber 100%. Outer: leather 100%. Lining: leather 100%. Designer style id :... more

Penny Slot Suede Loafers

Men's Kiton Penny Slot Suede Loafers - Brown cedar brown suede almond toe whipstitch detailing penny slot branded leather insole leather lining flat rubber sole slip-on style Size: 8. Gender: Male. Material:Calf Leather/Rubber/Calf Suede. more

Townee Penny Loafer

Men's VINNY'S Townee Penny Loafer - Brown - Loafers Smooth, glossy leather adds a refined touch to a timeless penny loafer you can wear from office hours to happy hour. Leather upper, lining and sole Made in Portugal Black Owned/Founded more

Vinny’S ’S Townee Leather Penny Loafers

Men's VINNY'S Vinny’S ’S Townee Leather Penny Loafers - Black Known for its dress shoes crafting history, the Danish brand, Vinny, presents its interpretation of iconic Penny loafers. Made from polished leather, they feature soft footbeds that offer... more

Alvin Penny Loafer

Men's Stuart Weitzman Alvin Penny Loafer - Black - Loafers A classic penny keeper and apron toe add timeless sophistication to a leather loafer grounded by a treaded rubber sole. Leather upper and lining/rubber sole Made in Italy more

Supersport Moc Toe Penny Loafer

Men's Allen Edmonds Supersport Moc Toe Penny Loafer - White - Loafers This hand-sewn penny loafer offers complete comfort with contoured support, shock absorption and stability. Memory foam cushioning Leather upper and lining/rubber sole Imported more

Andes Penny Loafer

Men's Born Andes Penny Loafer - Brown - Loafers Distinguish yourself from the rest with the smooth leather upper of the Andes slip-on driving loafer from Born. Leather or suede upper. Slip-on. Penny keeper pocket. Synthetic outsole. more

Penny-Slot Loafers

Men's Doucal's Penny-Slot Loafers - Gray chocolate brown grained texture almond toe penny slot branded leather insole low block heel rubber sole slip-on style Size: 42.5. Gender: Male. Material:Rubber/Calf Leather/Calf Leather. more

Wakith Penny Loafer

Men's ALDO Wakith Penny Loafer - Blue - Loafers Perk up your laidback outfit with the Aldo Wakith loafer. Be it the timeless penny slot or the classy leather upper, you can never go wrong with this round-toe slip-on. Leather upper. Slip-on. Round moc... more

Davis Penny Loafer

Men's Blake McKay Davis Penny Loafer - Brown - Loafers Look steezy in formal and casual attires by donning the Davis loafer from Blake McKay. The Italian leather loafer, designed with a penny slot, displays timeless fashion. Matching stitch accents... more

Webb Grained-Effect Penny Loafers

Men's Bally Webb Grained-Effect Penny Loafers - Black Black leather Webb grained-effect penny loafers from Bally featuring an almond toe, a slip-on style, a branded insole and a rubber-injected leather sole. Size: 44. Gender: Male.... more

Logo-plaque Slip-on Penny Loafers

Women's Miu Miu Logo-plaque Slip-on Penny Loafers - Blue Dimensions: Heel: 1cm 100% Calf Leather, 100% Rubber, 100% Calf Suede. Made in Italy. more

Zayna Water Resistant Penny Loafer

Women's Vaneli Zayna Water Resistant Penny Loafer - White - Loafers Strut your stuff rain or shine in this water-resistant leather penny loafer set on a platform lug sole and outlined with a studded welt. 1 1/4" heel Water-resistant Removable cushioned... more