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| Best Seller  | Men's J.Crew Alden For Suede Penny Loafers - Brown Founded in Massachusetts by Charles H. Alden in 1884, the Alden Shoe Company is now in its fourth generation and is the oldest shoemaker in New England. This exclusive-to-J.Crew take on the classic... ... more | go to store |
 | Alden For Straight-Tip Cordovan Boots Men's J.Crew Alden For Straight-Tip Cordovan Boots - Black - Casual boots Founded in Massachusetts by Charles H. Alden in 1884, the Alden Shoe Company is now in its fourth generation and is the oldest shoemaker in New England. This handsome boot is... ... more | go to store |
| Best Seller  | Founded In Massachusetts By Charles H. Alden In 1884, The Alden Shoe Company Is Now In Its Fourth Generation And Is The Oldest Shoemaker In New England. These Classic, Made-In-The-U.S. Penny Loafers Feature Soft Suede Uppers With A Goodyear Welt, Which... ... more | go to store |
 | Gently Worn 3x Max! Women's Leather Lug Sole Loafer A Lug Sole Horsebit Loafer With Blue Rosebud Print Lining On The Insole. A Mainstay In Gucci History Since The '50s, The Classic Horsebit Loafer Bridges The Past To The Present. A Homage To The... ... more | go to store |
 | Men's Alden Penny Loafer - Gray - Loafers Cut from smooth leather and set on a lightweight, flexible sole with a Goodyear welt, this sophisticated penny loafer is meticulously handcrafted in the USA. Leather upper and lining/leather and rubber sole... ... more | FREE shipping go to store |
 | Men's Alden Milkshake Penny Loafer - White - Loafers Crafted from supple suede, this handsome penny loafer features classic detailing for a timeless look and is supported by a sturdy sole. Leather upper, lining and sole Imported ... more | FREE shipping go to store |
 | Men's Alden Penny Loafer - Blue - Loafers Crafted from supple suede, this sophisticated penny loafer is made in the USA with contrast stitching and a lightweight, flexible sole. Leather upper, lining and sole Made in the USA Designer Shoes ... more | FREE shipping go to store |
 | Men's Alden Leisure Penny Loafer - Black - Loafers This penny loafer hand sewn from soft calfskin has been stained and polished to a classic patina, a hallmark of Alden of New England. A cushioned footbed and flexible, lightweight sole provide all-day... ... more | FREE shipping go to store |
 | Men's Christian Louboutin Penny Leather Penny Loafers - Brown Upper: leather. Lining: leather. Sole: leather insole, rubber sole. Toe shape: almond toe. Made in Italy. Includes: shoe box, dust bags. Designer color name: Rhea. ... more | FREE shipping go to store |
 | Le Loafer 15 Cassandre Moccasin Penny Loafers Men's Saint Laurent Le Loafer 15 Cassandre Moccasin Penny Loafers - Black Saint Laurent "Le Loafer 15" penny slippers in nappa calf leather Stacked heel Round moc toe Leather penny keeper strap with Cassandre hardware Leather sole Slipon style Made in... ... more | FREE shipping go to store |
 | Le Loafer Leather Penny Loafers Men's Saint Laurent Le Loafer Leather Penny Loafers - White Upper: leather. Lining: leather. Sole: leather insole and sole. Toe shape: round toe. Made in italy. Includes: dust bag, shoe box. Designer color name: pearl. ... more | FREE shipping go to store |
 | Alden For Cordovan Tassel Loafers Men's J.Crew Alden For Cordovan Tassel Loafers - Black Founded in Massachusetts by Charles H. Alden in 1884, the Alden Shoe Company is now in its fourth generation and is the oldest shoemaker in New England. We partnered with the brand for this... ... more | go to store |
 | Alden For Suede Tassel Loafers Men's J.Crew Alden For Suede Tassel Loafers - Brown Founded in Massachusetts by Charles H. Alden in 1884, the Alden Shoe Company is now in its fourth generation and is the oldest shoe and boot maker in New England. We partnered with the brand for this... ... more | go to store |
 | Men's Bruno Magli Tonio Penny Loafer - Black - Loafers Classic style meets everyday comfort in this moc-toe penny loafer fashioned from rich Italian leather. Cushioned footbed Leather upper and lining/leather and rubber sole Made in Italy ... more | FREE shipping go to store |
 | Men's Tod's Deconstructed Penny Loafer - Black - Loafers Designed for all occasions, this timeless penny loafer is rendered in smooth leather and stamped with the Tod's monogram for subtle signature style. Leather upper, lining and sole Made in Italy... ... more | FREE shipping go to store |
 | Men's G.H.BASS Larson Leather Penny Loafer - Brown - Loafers This classic penny loafer boasts handsome moc-stitching and classic beefroll details that pair equally well with crisp suits and casual shorts. Leather upper, lining and sole Imported ... more | FREE shipping go to store |
 | Men's Adieu Colorblock Penny Loafer - Black - Loafers A crepe-rubber sole with good traction grounds this colorblocked penny loafer that borrows from traditional menswear and the '60s music scene. Removable insole Leather upper and lining/rubber sole... ... more | FREE shipping go to store |
 | Handsewn Leather Penny Loafers Men's Peter Millar Handsewn Leather Penny Loafers - Brown Peter Millar penny loafers in luxurious leather with a rich matte finish Chunky heel Handstitched round moc toe Penny keeper strap Innovative foam insole Sheepskin lining Welted sole... ... more | FREE shipping go to store |
 | Men's VINNY'S Yardee Penny Loafer - Black - Loafers Enjoy the feel of luxurious Italian suede in this finely stitched penny loafer set atop a soft cushioned footbed. Cushioned footbed Leather upper, lining and sole Made in Portugal Black Owned/Founded ... more | FREE shipping go to store |
 | Men's Ferragamo Men Penny Loafer - White - Loafers A classic revised: gentlemen's penny loafer made of the softest italian calfskin. The leather is worked by artisans to achieve a natural shade and rich finish. Punctuated by a raised seam around the... ... more | FREE shipping go to store |
 | Men's Paul Stuart Hart Penny Loafer - Brown - Loafers Crafted from soft suede in a timeless silhouette, this dapper penny loafer is a must-have cornerstone of your formal wardrobe. Leather upper/synthetic lining/rubber sole Made in Italy ... more | $395.00 $256.75 FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | Men's Manolo Blahnik Perry Suede Penny Loafers - Brown Upper: leather. Lining: leather. Sole: leather insole and sole. Toe shape: round toe. Handmade in Italy. Includes: shoe box, dust bag. Designer color name: 2023 Dbrw. ... more | FREE shipping go to store |
 | Men's Brooks Brothers Greenwich Penny Loafer - Brown - Loafers Diversify your professional wardrobe with the Brooks Brothers Greenwich penny loafer. Crafted from supple leather, this pair sports a classic silhouette that pairs well with a myriad of... ... more | FREE shipping go to store |
 | Men's Bruno Magli Tonio Penny Loafer - Black - Loafers Classic style meets everyday comfort in this moc-toe penny loafer fashioned from rich Italian leather. Leather upper and lining/leather and rubber sole Made in Italy ... more | FREE shipping go to store |
 | Men's Thom Browne Varsity Penny Loafer - Black - Loafers Supple calfskin leather throughout ensures comfort and flexibility as it also elevates this handsome Italian loafer with a bit of branding on the heel loop. Leather upper, lining and sole Made in... ... more | FREE shipping go to store |
 | Men's Johnston & Murphy Baldwin Penny Loafer - Black - Loafers Supple sheepskin leather and a memory foam-cushioned footbed ensure all-day comfort in a handsome penny loafer. ... more | $195.00 $146.25 FREE shipping go to store |
 | Men's Johnston & Murphy Baldwin Lug Penny Loafer - Green - Loafers A penny keeper strap and moc toe add a classic touch to this dapper leather loafer grounded on a lightweight, flexible sole with grippy lugs. Water-resistant Cushioned footbed with arch... ... more | FREE shipping go to store |
 | Men's Vintage Foundry Thomas Penny Loafer - Black - Loafers Give a perfect finishing touch to your sophisticated look with the Thomas penny loafer from Vintage Foundry Co. This leather slip-on is designed with a cushioned footbed to improve underfoot... ... more | FREE shipping go to store |
 | Men's Mezlan Galeno Penny Loafer - Black - Loafers A suede upper and classic penny keeper bring office-ready polish to a Spanish-crafted loafer finished with a streamlined apron toe. 1" heel (size 11) Leather upper, lining and sole Made in Spain ... more | FREE shipping go to store |
 | Gisborne Leather Huarache Penny Loafers Men's Rodd & Gunn Gisborne Leather Huarache Penny Loafers - Brown Rodd amp; Gunn huarachestyle penny loafers made from soft, supple leather with expert handwoven lasercut detailing Flat heel Round toe Penny keeper strap Leathercovered molded footbed... ... more | FREE shipping go to store |
 | Men's Saint Laurent Le Loafer Penny Mone Sizeles - Black - Loafers Penny loafer mules with a hand-stitched apron-toe construction. ... more | FREE shipping go to store |
 | Men's Scarosso Raimond Slip-on Penny Loafers - Blue Dimensions: Heel: 2.5cm, Sole: 0.5cm 100% Calf Leather, 100% Suede, 100% Leather. Made in Italy. ... more | $403.35 $259.99 FREE shipping go to store |
 | Men's Florsheim Rucci Weave Penny Loafer - Black - Loafers Amp up your formal ensemble with the Rucci Weave penny loafer from Florsheim. Intricate woven patterns bring unique charm to the classic design of this leather slip-on. Soft lining, fully... ... more | FREE shipping go to store |
 | Men's Boss Derreck Penny Loafer - Brown - Loafers Rich calfskin leather elevates an Italian-crafted penny loafer that will make the perfect addition to your everyday office wardrobe. Leather upper and lining/leather, rubber and synthetic sole Made in... ... more | $299.00 $194.35 FREE shipping go to store |
 | Thom E Shearling Penny Loafers Men's Thom Browne Thom E Shearling Penny Loafers - Black Calfskin suede loafers in brown. ... more | FREE shipping go to store |
 | Men's Sandro Moscoloni Taylor Moc Toe Penny Loafer - Brown - Loafers Elevate your fit with a moc-toe penny loafer crafted from burnished leather with a cushioned footbed and flexible rubber sole. Cushioned EVA footbed with arch support Leather upper... ... more | FREE shipping go to store |
 | Medusa Coin Penny Driving Loafer Men's Versace Medusa Coin Penny Driving Loafer - Natural - Loafers Set on a segmented driver sole with Greek-key tread, this calfskin-suede loafer features a Medusa-head 'coin' inserted in the keeper strap. Removable insole Leather upper and... ... more | FREE shipping go to store |
 | Ron Haydon Weatherproof Penny Loafer Men's Ron White Ron Haydon Weatherproof Penny Loafer - Brown - Loafers A classic penny keeper and supple suede upper lend timeless sophistication to a luxe loafer grounded by a cushioned footbed and slip-resistant lug sole. Multilayered,... ... more | FREE shipping go to store |
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