The loafer has been around since the 1930s and has spent most of its life being underestimated.
It was the shoe prep school students wore in the 1950s, that Italian men perfected on the terraces of Portofino in the 1960s, and that Gucci turned into a status object with the horsebit in 1953. It disappeared from serious menswear conversation through the 1990s and 2000s, outcompeted by the Chelsea boot and the white trainer, and then came back harder than almost any other shoe in the wardrobe.
Where it Came From
The loafer’s origins trace back to a Norwegian farming shoe called the møkkasin, a slip-on moccasin design that Gucci designer Aldo Gucci encountered while travelling in the 1930s. Bass introduced the Weejun in 1936, a penny loafer with a diamond-shaped slot on the strap, which American students began filling with coins for payphone calls. The coin slot became decorative, the name stuck, and the penny loafer became the default shoe of the Ivy League wardrobe.
Gucci’s horsebit arrived in 1953, hardware borrowed directly from equestrian stirrup design, and it set the template for what a luxury loafer should look like. Gianni Agnelli wore them constantly, often with a suit and invariably without socks, and that image became one of the defining pictures of mid-century European style.
Why it Came Back
The loafer’s return over the last five years is tied to the broader shift in menswear away from structured, formal dressing toward something softer and more relaxed. As suits loosened and the overall energy of men’s fashion moved toward quiet luxury and considered casualness, the loafer became the obvious shoe. It sits between the formality of an Oxford and the casualness of a trainer, works across most outfit categories, and carries genuine history without requiring much explanation.
The Types Worth Knowing
The penny loafer is the most versatile, a round toe and a clean strap, available in dark leather for formal use and tan or suede for casual wear. This is the one to own if you are buying your first pair.
The horsebit is the dressier option, metal hardware elevating it toward formal territory, pairing well with a suit, tailored trousers, or smarter casual dressing. Gold hardware reads as summer. Dark hardware reads as year-round.
The tassel loafer is the American preppy version, traditionally in burgundy or tan leather, working well with chinos and blazers in a smart casual context. The driver moccasin is the most casual of the group, with a rubber pebble sole, suited to warm weather and genuinely relaxed dressing.
How to Wear Them Without Socks
The sockless loafer works in warm weather and in any context where the overall outfit is relaxed enough to carry it. The trouser length matters more than most men realise. A full-length trouser worn sockless creates too much fabric and makes the whole thing look like an accident. Cropped trousers or chinos sitting a couple of inches above the ankle are correct. Rolled jeans work too, as long as the roll is clean and deliberate.
The shoe needs to fit slightly more snugly than one worn with hosiery, since a sock adds volume that bare skin does not. If the heel slips sockless, the shoe is too large. For anyone who wants the look without the practical concerns, a no-show sock in a skin tone sits inside the shoe and remains invisible from outside.
What to Wear With Them
A suede penny loafer in tan or mid-brown with cropped chinos and a plain white shirt is the cleanest casual version. With tailoring, a dark leather horsebit or penny loafer with a navy or grey suit works at a summer wedding, a smart lunch, or a creative office. With jeans, tan or brown suede rolled once at the ankle covers most occasions and is one of the easier combinations to get right.
The ones worth buying
Gucci’s Jordaan horsebit remains the reference at £550 and above. Tod’s Gommino is the classic casual option at a similar price. Loake makes well-constructed penny loafers in the £150 to £200 range. For something more accessible, Massimo Dutti and Mango both carry the silhouette credibly at a fraction of the designer price. Buy leather or suede, avoid synthetics, and rotate with at least one other pair.