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.

Construction decides what the shoe is for and how long it lasts. A handsewn moccasin, which is what the Weejun and the Alden LHS are, wraps the vamp by hand, so it flexes like a slipper and always reads casual. A Goodyear welt adds a leather strip stitched to the upper and insole, so the sole can be cut away and replaced without touching the shoe above it. Blake stitching runs straight through to the insole: sleeker and closer-trimmed, but it needs a Blake machine to redo.

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.

Shell cordovan is the upgrade people argue about. It comes from a dense membrane in a horse's hindquarters, Horween in Chicago takes about six months to tan it, and it creases in rolls rather than cracking. It also nearly doubles the price and runs warm in summer. Past about $600 you are paying for a closer-trimmed waist, a finer sole edge and hand finishing. Real craft, no extra mileage.

The money argument for the $400 pair is the resole. A Goodyear-welted loafer takes four to six rebuilds before the welt gives out, at $95 to $160 a time, and Alden runs a factory recrafting service in Massachusetts. A $110 Weejun is cemented and is a two-or-three-year shoe by design. Neither is wrong. Just count the resoles before deciding which one is expensive.

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.

The fit lives in two places: the throat line across the top of your foot and the heel cup. Leather stretches across the width and never in length. If you get heel slip, do not size down again. Ask a cobbler for a tongue pad, a thin felt wedge glued under the vamp, which pushes your foot back into the heel and costs about $15.

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.