Style Basics

The definitive guide to the loafer

By on July 5th, 2014

Ah, loafers. The often underrated and historical shoe that men have been wearing not only for their slip-on ease, but also their comfort and simplistic style.

In a nutshell, a loafer is a lace-less, low cut shoe with a low heel.

And lots of guys have a bias towards these shoes. Some even avoid them altogether thinking that they are too casual. But if you don’t have a pair of loafers in your closet then you’re missing out. So, I’ve taken it upon myself to provide you a brief guide on the venerable loafer.


It all started back in the 1930s when Norwegians began exporting leisure slippers to neighboring countries in Europe. The shoes were actually originally worn by dairy farmers!

Well traveled Americans started taking note, but it wasn’t until Esquire magazine wrote a feature that their popularity really took off(1).

As with any good story the facts are often disputed. And it’s no different with the story of the penny loafer. These shoes came about when an enterprising man by the name of G.H. Bass put an additional piece of leather across the top of the shoe. The leather was then slit just wide enough to place a penny inside. Apparently, back in the 1930s a phone call at a payphone cost 1 cent. It was young people that would place a penny in their shoes for an emergency phone call should they find themselves stuck on the other side of town.

However, there is a disputing side of the story that claims the penny loafer came about after American prep school students in the 1950s wanted to make a fashion statement(2).

The takeaway here is that now there was a piece of leather – purely ornamental – across the front of the shoe. The loafer was now making it’s way into the fashion scene.

Gucci introduced a metal strap across the front of the shoe and these started to become popular with American businessmen. About the same time, tassels made their first appearance.

Long story short, American men were not only wearing casual loafers at home and on the weekends, but at the office too. Fast forward a few decades and the loafer (penny loafer, or not) is firmly situated among the gray area that is formal/casual.

BE advice

So, what’s a guy to do when shopping for loafers?

Here’s the big thing you need to know – loafers are inherently casual as a result of their background. So no black tie events or weddings. However, that’s not to say that you can’t wear them to the office.

Here are some guidelines.

At the office: Pick a great looking pair of loafers. They should be of a hand-rubbed leather with a great shape and thin soles. No scuffs, no tears. You want a pair of shoes that will command respect and complement your custom suit or sport coat.

The weekend: Now you can choose a pair with thicker soles. The leather shouldn’t be quite as flashy, but more casual looking. Who knows, you may be hitting the pool!? 

Should you wear socks? Well, in the summer time, the BE crew says no. However, for those chilly fall and spring days you are probably OK wearing socks. Especially, if you have a real nice pair of loafers that you are pairing with a suit. And don’t forget to take good care of them by using a shoe tree.

Further reading:

History of a shoe: Penny loafers