Penny Loafers

Originating as a Norwegian fisherman's shoe, the penny loafer found its way into the American fashion sphere in 1936 (largely credited to designer G.H.BASS). According to style legend, the nickname harkens back to the practice of Ivy League students tucking pennies into the top slots of their loafers to use at payphones. And, while the slot is still considered a quintessential part of this preppy silhouette, penny loafers now occasionally feature a horsebit embellishment, tassels, or forego the strap entirely.

Men's Casual Penny Loafers. With features like edgy lug soles, colorful accents, and moccasin detailing, men's casual penny loafers transcend seasonal trends and style pigeonholes by catering to a wide range of wardrobes. Made to complement your weekend wanderings, they're a 5-to-9 sartorial staple you can pair with jeans and a T-shirt or chinos and a sweater.

Men's Dress Penny Loafers. On the other end of the spectrum, men's dress penny loafers are an easy way to elevate your workwear and occasion suiting alike. Designers like Bruno Magli, Santoni, and To Boot New York are among many in our collection to nail this sophisticated style--often in timeless neutrals, but occasionally with unexpected takes like bold hues, color-blocking, and basketweave finishes.

Men's Suede Penny Loafers. Inject textural warmth into your look with suede men's penny loafers. Whether you want to invest in literal blue suede shoes or something more understated, suede penny loafers offer a vibe that's slightly relaxed compared to polished leather iterations (but are every bit as dapper).

Men's Designer Penny Loafers & Slip-Ons. When it comes to designer penny loafers, look to the brands you already know, love, and trust, like Gucci, Ferragamo, and so many more. Here, you'll find penny loafers abundant with logo-print jacquard and signature hardware--and plenty of stripped-back, streamlined pairs, too.