Men's Penny Loafers

The name ‘penny loafers’ comes from a style detail that became popular in the 1950s. The classic leather strap across the top of the shoe, known as a saddle, features a small slit – just big enough to fit a penny. American students would tuck a coin into each shoe, supposedly to use for emergency phone calls. Over time, the name stuck, and penny loafers became a timeless footwear staple.

Penny loafers are one of the most versatile shoes you can own. For a polished look, add them to your office-wear rotation and wear them with a three piece suit to add a refined endnote to your everyday tailoring. For smart-casual dress codes, pair with tailored chinos or flannel trousers to show off the shoe. In summer, they pair nicely with linen trousers or shorts, worn sockless or with invisible socks for a clean finish. For a more classic take, stick to darker leather tones like black or brown, while suede loafers give a more relaxed, contemporary look.

Absolutely. While they’re often associated with more formal outfits, penny loafers work just as well in a laid-back setting. Pair them with jeans and a t-shirt for an understated look, or wear them with chinos and a long-sleeve polo for easy weekend style. Suede loafers in particular lend themselves to a more casual feel, especially in neutral tones like tan or navy. Whether dressed up or down, penny loafers bring a refined finish to any outfit.