Though the prep sartorial tradition comes and goes in waves in America, it’s never really out of fashion. We often think of critter-laden trousers and boat shoes as typically preppy, and with good reason. Sometimes, though, we overlook a classic shoe that became popular with the preppy set and has since become a household name: the penny loafer.
Penny loafers are laceless shoes with a moccasin-style upper that’s stitched to a separate sole and heel. They have a strip of leather called a “saddle” that sits horizontally across the instep. Nowadays, a broader definition can include any shoe that has such a strap, regardless of its construction.
The saddle is sometimes referred to as a “penny keeper.”
We will refer to this shoe as a “penny loafer,” “penny slip-on,” and “penny” throughout this article. More on that below.
G.H. Bass & American Style
In the mid-1930’s (some records say 1934, others say 1936), G.H. Bass put their own spin on Norwegian slip-on shoes, basically stitching a heel to a moccasin-style upper. They added a strap of leather across the upper vamp (referred to as a “saddle”) and sold them as casual house shoes. They called them “Weejuns” (to sound like “Norwegian”), and the term is still copyrighted by Bass today.
They became known as penny loafers, and they went from being “indoors only” shoes to being a workhorse of many gentleman’s casual wardrobes.
Why Are They Called Penny Loafers?
In the 1950’s, prep school students regularly wore Weejuns with their chinos and sport coats or blazers. The saddles of Weejuns had a diamond cut-out shape in the center, and it was common at the time for young people to put pennies there. It’s not exactly clear why this was a thing, but there are some theories:
- Two pennies were all you needed to make an emergency phone call
- Simply make a fashion statement
- Pennies would bring good luck
The practice of putting pennies in the saddle of Weejuns led to the widespread use of the term “penny loafer.” In fact, Cole Haan, an American footwear brand formed in 1928, sold a penny loafer that came with actual pennies in them back in 2008 for their 80th anniversary. That’s about as #throwbackthursday as it gets.
Different Penny Styles
Not all penny loafers are created equal. Though there are different styles of shoes that incorporate a saddle, we will refer to them as either “penny” or “penny loafer” unless intentionally being more specific.
A blind penny is the same as a penny loafer, except that the diamond cut-out in the saddle’s center is either filled in or non-existent. It is thus “blind.”
This is a classic aesthetic detail typically seen on Weejuns and similar models. The plug (part of a loafer wherein the vamp is stitched to the sides) is exaggeratedly large and takes on the look of a beef roll. It’s a casual, handsome detail that you won’t find on dressier slip-ons that have penny keepers.
You’re probably asking, “Wait, aren’t loafers the same thing as slip-ons?”
Sort of, but not really. The difference hinges on how much influence a moccasin, the prototype for these two styles, has on their construction.
“Loafer” refers to a laceless shoe with a moccasin-style upper stitched to a separate sole and heel. “Slip-on” refers to a laceless shoe whose upper is not constructed like a moccasin. Slip-ons tend to be preferred by businessmen because they can be worn more easily with suits due to their dressier nature. A penny slip-on is simply a slip-on shoe with a penny keeper sewn onto the vamp.
Granted, “penny slip-on” isn’t an industry-wide term, but it’s a distinction that’s worth making. You don’t want to wear a penny loafer with a business suit, but you do want to wear a penny slip-on. Keep in mind that the shoe industry will refer to both styles as a penny loafer regardless of whether or not it’s technically correct to do so.
Another term that doesn’t really exist in the footwear industry but should, a penny moccasin is simply a laceless, heel-less shoe with a saddle across the vamp. Much more casual than the loafer or slip-on version, it’s on par with a driving shoe in terms of dressiness and construction.
How To Wear Penny Loafers
If our conversation includes moccasin, loafer, and slip-on versions, then you can safely wear any style penny with anything except a tuxedo.
- Jeans: Moc or loafer in any color. If jeans are dark and slim, a penny slip-on will work.
- Casual trousers: See jeans
- Suits: If light or more summery, mocs and loafers will work without socks. If it’s a darker business suit, a penny slip-on will work well
- Tuxedo: Don’t wear any style penny with a tuxedo
As penny loafers are available in nearly every color and material imaginable, they can be worn any time of year. Here are some suggestions for styles by season:
- Spring: Loafer or moc in light brown/tan leather or suede, slip-on in British tan
- Summer: Loafer, moc, or slip-on in white or bone-colored suede or nubuck
- Autumn: Dark brown distressed leather loafer, varigated brown slip-on
- Winter: Black or burgundy loafer or slip-on in leather or cordovan
Common Fit Issues
Everyone’s foot is built differently, and most people have some sort of irregularity with their feet. As it relates to penny loafers (or any laceless shoe that doesn’t use elastic in its construction), those with a high instep may have issues.
A high instep describes a foot in which the instep has a protrusion of some sort. This makes fitting certain shoe lasts uncomfortable. As loafers have little give, someone with a high instep will often have trouble wearing these comfortably. The saddle of a penny loafer simply applies more pressure on the instep, exacerbating the problem. The same issue applies to bit loafers.
This isn’t to say that a man with a high instep won’t ever be able to wear a penny loafer. It just means that you’ll have to try on a few pairs from a few different brands, and that may mean ordering a bunch online and returning those that don’t work. It may also mean spending a day out at some shoe stores trying on everything you see until your foot tells you, “Yes, these are the ones.”
Not a bad day, we think!
Who Makes The Best Penny Loafers?
Pretty much every shoemaker makes penny loafers. Here are some firms that we feel do it particularly well:
- G.H. Bass: $110-$325
- Allen Edmonds: $175-$650
- Rancourt & Company: $295-$2800
- Undandy (you can design your own penny slip-on!): $190
Do Pennies Belong In My Closet?
Every man, no matter what his job, age, or social circumstances should own a penny loafer. They are simply so versatile and classic that they offer some of the best return-on-investment that any shoe can offer.
If you don’t wear suits every day, make it one of the first pairs you buy and wear them with nearly everything. If you do wear suits every day, make them the third pair you buy, right after an oxford and a derby. You have to wear something on the weekends!