Penny Loafers

First originating in the 1930s, penny loafers deviate slightly from the typical, clean, unadorned loafer, as they have a single strap that runs across the instep of the shoe. The strap has a slit in the center, and people hoping to make a fashion statement of their own began to display objects in the tiny pocket. And by the 1950s and 60s, penny loafers had become a symbol of “cool”.

Constructed of heavy black, brown and mahogany leather, with no laces or buckles, these loafers were designed with a strap across the top in the shape of a pair of lips. Soon, wearers were using this decorative feature to carry a small object, most often a penny. By the 1960s, the penny loafer was synonymous with casual fashion, a look that could be dressed up or down and worn by both men and women.

Penny Loafers for Women

Patent Leather Signature Penny Loafer
*Purchase at Cwonder

Softspots ‘Maven’ Penny Loafer
*Purchase at Nordstrom


KG by Kurt Geiger Women’s Lennard Penny Loafer
*Purchase at Amazon


The penny loafer got a boost in popularity when famous people such as actors James Dean, Steve McQueen and Don Johnson were seen wearing them on screen. President John F. Kennedy and singer Michael Jackson wore them in public. Penny loafers have been worn by both sexes since they first appeared, though more often by men. However, women’s penny loafers have many different styles. These versatile shoes were easy to slip on and comfortable for everyday wear. Their versatility has enabled them to make a smooth transition from work to play. The shoe can be worn with almost any attire, including suits, jeans and shorts.

Penny Loafers for Men

Cole Haan ‘Air Monroe’ Penny Loafer
Cole Haan ‘Air Tremont’ Penny Loafer
Cole Haan ‘Air Aiden’ Penny Loafer
*Purchase at Nordstrom


Wearing penny loafer can be just simple to do. For women, pair flat penny loafers with long, skinny jeans for a smart casual look. Wide-leg trousers and pants should lightly brush the ground when standing; pants that are too long or too short can make the shoe stand out and make your outfit look less tailored and sloppier. On the other hand, capri pants and mid-length to knee-length skirts highlight your shoes, so complement your outfit with a penny loafer that is more decorative or dressier. Loafers with sequins, bows or lace or in metallic colors will vamp up your outfit for the night out or for work wear. And for men, classic, simple penny loafers can offer informality and a more casual look when worn with a business suit. Fancier, more decorative styles can add an air of sophistication to casual shorts or a weekend outfit.  As a general rule, white socks or noticeable socks are best avoided when wearing penny loafers, especially when complemented with shorts. If you are wearing slacks or business pants, choose a dark-colored sock that matches the pants color. Simple, classic penny loafers can easily go well with any type of outfit. Penny loafers are a timeless shoe style suitable for any age range and for both genders.