The Best Penny Loafers at Every Price Point

The penny loafer has been a menswear constant since the 1930s, when Norwegian cobbler Nils Gregoriusson Tveranger adapted a traditional fishing shoe into what became the Aurland loafer. Today, penny loafers span from casual to dressy depending on construction and material.

Under $150: Bass Weejuns. The original American penny loafer, introduced in 1936, remains the entry point. The beef-roll construction gives it a distinctly casual Americana feel. At $110, the Larson model in burgundy or tan is the best value in the category.

$150 to $300: Grant Stone Traveler Penny Loafer offers Goodyear-welt construction at a price that would be impossible from European makers. At $250, these use full-grain calfskin and a leather sole that can be rebuilt.

$300 to $500: Alden Leisure Handsewn Penny Loafer delivers American bench-made quality. The unlined construction creates a flexible, moccasin-like feel, and the chromexcel leather develops a rich patina over time.

$500 and above: Crockett and Jones Harvard loafer and Edward Green Piccadilly represent the English tradition, with a sleeker profile and closer-trimmed sole. Italian makers like Baudoin and Lange produce even sleeker versions at the $600 to $800 level.

Regardless of price, the penny loafer should fit snugly out of the box, since the leather stretches. Go a half size down from your sneaker size. Browse the full range from Grant Stone at https://www.grantstoneshoes.com.

Own at least one pair of penny loafers. They fill the gap between sneakers and dress shoes that nothing else covers as well: polished enough for smart casual, comfortable enough for all-day wear, and timeless enough that you will never look at them and think they are dated.