Receive a free copy of our magazine when you sign up.

How To Wear Loafers – A Simple Guide To Wearing A Classic

Even wondered how to wear loafers? The classic loafer has been an essential piece of menswear since its invention in Norway in 1930. Its brief history goes something like this:

  • 1930: Nils Gregoriusson Tveranger introduces a new design called the ‘Aurland moccasin’ (later renamed the ‘Aurland shoe’) in Norway.
  • Later 1930s: The Spaulding family in New Hampshire starts making shoes based on Tveranger’s design and calls them ‘loafers.’
  • 1934: G.H. Bass begins making loafers under the name ‘Weejuns’ (as in, Nor-wegians).
  • 1950s: Loafers become a significant part of the men’s casual shoe canon.

And now… Loafers continuously cycle in and out of trendiness, but always remain a menswear staple. Over the years, loafers have become increasingly diverse and inventive, with designers pushing the boundaries of casual footwear and marrying high-fashion fearlessness with classic, comfortable style.

Today we’re showing the loafer a little love, with our essential guide to menswear’s most beloved slip-on shoe.

In Depth: How To Wear Loafers & Loafer Types

As you can probably imagine, when you’ve been around for almost 80 years, you undergo some changes. The loafer has endured update after update, continuously evolving with the changing times. Here are a few styles you may encounter in your search for the perfect loafer:

The Penny Loafer


As classic as classic gets. The penny loafer has a leather strap across the top of the shoe, with a diamond-shaped slot just wide enough to hold a small coin. One theory states that the coin was a fashion statement devised by American prep school students in the 1950s. Another says the change was carried in case the wearer needed to make an emergency phone call. Either way, the style has become a fashion legend.


The Tassel Loafer


The actual origins of the tassel loafer are unclear, but one possible story involves a Hungarian-American actor who owned a pair of Oxfords with tassels at the ends of the laces. The Alden Shoe Company was tasked with making something similar, and came up with a slip-on pattern that used the tassel as a decoration. In 1950 they launched the shoe after experimenting with the design, and the tassel loafer was a hit.


The Snaffle Loafer


You have Gucci to thank for this one. The snaffle loafer – aka the Gucci Loafer – was introduced in 1968. Its distinguishing feature was a golden brass strap in the shape of a horse’s snaffle bit laid across the front. Gucci also turned the traditionally brown loafer black, making it just formal enough to be worn with suits. A loafer revolution was born, and big names like Gianni Agnelli and John F. Kennedy went on to sport the shoes.


The Apron Loafer


Apron loafers are identifiable by visible edges or stitches that finish off the toe (thereby forming a sort of ‘apron’ along the shoe’s front). Also known as moc toe, apron loafers feature a separate piece of leather that extends from the bottom of the top line around the shoe itself. The resulting stitching line gives the impression of a ‘crease’ between the top of the toe and the bottom.


Inspiration & How To Wear Loafers

Knowing the options available is only half the battle. Once you’ve got loafers in your wardrobe, the next step is learning how to rock them with style and swagger.


How To Wear Loafers

How To Wear Loafers

The loafer can replace just about any other shoe in an off-duty outfit, while adding an extra dash of dapper to the look. Casual loafers can be worn with denim and khakis, and sockless with shorts during warm seasons. Go for jeans and a t-shirt if you want to keep things relaxed, and a shirt and chinos if you want something with a little more class.

Smart Casual

How To Wear Loafers

Loafers naturally straddle the divide between formal and informal, making them ideal for a smart casual ensemble. When you’re talking chinos or tailored shorts on the bottom, and blazers and button-downs on top, tasselled loafers are a winning option. A sleek Gucci-style loafer is also a polished choice. Aim for smart first and casual second.



While loafers will never be black tie material, it’s not impossible to wear loafers them with a suit. A hyper-tailored, 3-piece business number is too much for a loafer, but a more casual suit or a blazer/sport coat combination works. Look for dark colours, high-quality materials, a refined shape and minimal distracting details.

The Great Sock/No Sock Loafer Debate


To sock or not to sock? That is the question. The beauty of fashion is that all rules are meant to be broken, and at the end of the day it comes down to personal preference. Socks with loafers are like pocket squares – rock them if you like them, don’t if you don’t. The sockless look has been trendy lately, so consider it if the weather and occasion allow.


Sign up now,
you magnificent bastard.

Access exclusive content, be the first to know about giveaways
and receive news before your mates.