Although never as big as some of the other more memorable trends of the time, penny loafers were absolutely something you saw people wearing in the 1980s and 1990s. Here’s how a traditional shoe design from the 1950s came to be remembered as an 80s and 90s trend.
When were penny loafers popular?
In interviews with tastemakers in the mid 80s, they described penny loafers with jeans as a hybrid 50s/80s look. And indeed, the penny loafer as we know it today was introduced in the 1950s. But there’s a reason today we associate them with the 80s more than the 50s.
Based on the sheer number of mentions in newspaper advertising, it would seem that penny loafers peaked in popularity in 1989 and 1990, but with similar peaks in 1986, 1992, and 1995. But unlike some 80s trends like, say, jams shorts, penny loafers never faded away. Instead, they seem to have flipped from timeless to trendy a couple of times.
So while penny loafers started out as a throwback look in the 1980s, the look caught on and they became more popular in the 80s than they’d been in the 50s.
What did 80s penny loafers look like?
Traditionally, penny loafers have a decorative slot in the top of the shoe, also called the vamp. In the 80s, it was fashionable put a real penny in that slot in the vamp. I can remember ’80s commercials when someone was having a sale and they wanted to make the point of how low their prices were, they would show someone scrounging for change in couch, cushions and prying the pennies out of their penny loafers. It was contrived, but the point wasn’t lost on us. If we didn’t have a pair of penny loafers ourselves, we knew someone who did.
We typically associate tight rolled jeans with expensive athletic shoes, as a way to call attention to your Air Jordans. But I absolutely remember people tight rolling their jeans with penny loafers. It may have been a matter of practicality. Penny loafers usually cost less than most athletic shoes did, and if you rotated them on alternating days both of them would last longer.
What they cost in the 1980s
As for the cost, it varied. Discount store versions of penny loafers from stores like Target or Venture cost as little as $7 in the mid to late 1980s. Department store versions from stores like Dillard’s, cost more like $60. And I was able to find a modern penny loafer that costs $499, which implies the existence of $199 penny loafers in the 80s.
The main reason I remember penny loafers at all was because there was a kid in my class who would call out anyone whose shoes he knew cost less than his penny loafers. In effect, the penny loafers called attention to his Air Jordans. But since he didn’t seem to get enough attention just from that, he would find ways to point out others whose shoes were less expensive than his, sometimes subtly, and sometimes not so much.
I’m not sure if being snobbish about something called a penny loafer was more of an ’80s thing or a St. Louis thing. It seems farcical and petty now. And don’t get me wrong, the ’80s weren’t all bad. There are definitely things about the 80s I miss. But the pettiness isn’t one of them.
What to wear to an 80s retro party
Penny loafers never completely went out of style and are still available today because of their versatility. They can be casual if you want and they can be dress shoes if you want. If want to know how to dress for a retro 80s party, you can do much worse than a pair of penny loafers and some tight-rolled jeans. Shoving pennies into the slot in the vamp is optional but would add a touch of authenticity.
David Farquhar is a computer security professional, entrepreneur, and author. He started his career as a part-time computer technician in 1994, worked his way up to system administrator by 1997, and has specialized in vulnerability management since 2013. He invests in real estate on the side and his hobbies include O gauge trains, baseball cards, and retro computers and video games. A University of Missouri graduate, he holds CISSP and Security+ certifications. He lives in St. Louis with his family.
In the late 80s/early 90s, in my very “preppy” school district, shoes very similar to this were popular. But I think you would call them “boat shoes”? Leather loafers… no slot, but a small leather knot. I remember there being a very closely associated brand (like how Jansport backpacks were all the rage), but for the life of me I can’t remember what it is. From Knoxville, TN.
I remember getting a pair of leather loafers for work once, and my wife called them boat shoes. First I’d heard the term, my recollection of them matches your description. I’ll have to ask her about it.