To Penny, or Not to Penny?

Few shoes are as essential in the modern menswear landscape as the classic leather loafer. Whether you’re dressing up or dressing down, it is the “the Swiss Army Knife of shoes,” an any-occasion solution to many footwear conundrums. But within the broader loafer genus, one particular species—the penny loafer—includes a divisive design feature: a small, coin-shaped slot in the leather strap “saddle” across the vamp of the shoe.As the lore goes, Ivy Style pioneers and sock-hopping teens in the mid-20th century liked to store a penny in their shoes as “payphone change.” But now that payphones are a thing of the misty-eyed past and the American one-cent penny is no longer minted for circulation, is it still cool to put a penny (or any other coin, or coin-shaped object) in your penny loafers? What is the line between timeless and passé?We invited two of GQ’s most well-heeled staffers, associate grooming and wellness editor Tyler Chin and senior style commerce writer Gerald Ortiz, to ponder the pros and cons of the penny loafer.Mahershala Ali, an ostensible penny proponent, in London on October 19. Getty ImagesIn general, should one wear a penny in their penny loafers? Why or why not?Tyler Chin, associate grooming and wellness editor: Sure! I’ve seen so many guys wearing loafers these days, and yet still haven’t seen any of them harking back to the shoe’s origins with a penny in them. Maybe I’m not looking hard enough or I’m not in circles where they are doing that, but it’s an inoffensive and easy way to accessorize the shoe. Plus, I had an English teacher in high school who did it, and while she wasn’t particularly cool, I did think the sartorial choice was neat.Gerald Ortiz, senior style commerce writer: No. I feel like guys who put pennies in their loafers are either try-hards, or just learned about that particular piece of prep trivia. The only acceptable instance to wear a penny in your loafers is if you’re really about that prep/Ivy style, like Preppy Pete, or the guys who frequent Alfargo’s Market (shout out).Does the coin have to be a penny? Can it be, say, a dime? (Some people use objects too, like buttons, tokens, etc.)TC: I think the penny would be the most boring and obvious choice. If a quarter could fit in there, I think it’d be so funny if you were at a vending machine and short a few cents and settled up with the coin in your shoe. One time, the button on my pants fell off on the street and I lost it, but imagine I had a spare button in my shoe? I could reattach it right there and then! In the hypothetical I’d also need to be toting around a sewing kit, but hey, I’d love to think I could be MacGyver in that scenario.GO: It doesn’t have to be anything at all. But if you’re going to do it, I don’t see why it couldn’t be another coin or object. It could be a Chuck E. Cheese token. Whatever you put in the slot, it would still be wack.What is the coolest type of currency one could wear in a loafer?TC: I just got back from a trip to Tokyo, and I had a lot of leftover yen coins. Two of them—the five and 50 yen—have a hole on them, which differentiates them from your boring American coin. I’d throw one of them in my shoe and be one of those people who never stops talking about their travel abroad.GO: I saw on Instagram someone stick a hundred dollar bill into their loafer and that was funny for a second. Then I scrolled on to the next meme.Should the coin be shiny or have a bit of patina?TC: I’m pretty sure a coin that is that close to the ground will surely have a patina before the end of the day. Also, I can’t remember the last time I’ve seen a shiny new coin—who carries loose change these days anyway?!GO: You know, it might be kind of cool to see a penny completely covered in verdigris slotted into your loafers. But maybe the coin should match the sheen of your loafers. I dunno, just don’t do it and you won’t have to think about it.What is the best outfit to wear with a pair of penny loafers?TC: Everyone I know is very familiar with my love of penny loafers. Lately I’ve been wearing them with bootcut jeans that are just a little longer than usual, so they have a nice drape over the shoe. Top-wise, I’d go with a tucked-in button up, T-shirt, or sweater. Pretty much anything that would go well with sneakers would be equally suited for wearing with loafers. Which is nearly all outfits.GO: Penniless or not, a pair of wide khakis with a clean-to-slight break and a striped button-up is a failsafe outfit. It wouldn’t be very inventive, but it would pass muster for most conceivable situations. Vintage straight-leg jeans with good fades, a fucked-up band tee, and a sportcoat is also a great look. But the best looks are always the unexpected pairings.What do you think of loafers that have a faux penny slot that cannot actually hold a coin?TC: It’s sort of like how guys will go on and on about having functional sleeve buttons on a suit jacket. Is there any situation where you’ll actually need to unbutton those or do you just leave one or two undone to “stunt” on your unimpressed bros? If you really want to put a coin in your shoe for the sake of accessorizing your footwear, then by all means get a shoe with a functioning penny slot and use it! But if you’re doing it just so you can say “Yeah, these joints are the real deal!” and use it as an excuse to talk about the history of the shoe and why yours are superior, then I’d rather you wear lace-ups.GO: I think it’s fine, even preferable to have a faux penny slot. It’s like how jeans still come with the watch pocket. It’s purely vestigial at this point, but would feel incomplete without it.How does the end of the penny factor into this? Does this make the penny more covetable as an accessory?TC: One of these days, I’ll be telling my great-great grandchildren about the origins of the penny loafer and they’ll be confused because they would’ve never heard or seen the one-cent coin before. I’ll whip one out of my shoe and instead of being impressed they’ll chalk it up to another one of Old Man Ty’s tales from his youth, and tuck me back into the nursing home they checked me into.GO: Lol. I guess it’ll make the penny more covetable. But it’ll be a long time before the penny becomes that desirable. That said, I love this British brand Six 95 that’s designing cool pieces using coins, so I can absolutely see more labels farming pennies for their clothes and accessories.TC: Men will break up anything other than a toxic relationship. Loafers did nothing wrong and sometimes it’s just the person wearing them that needs to hit the curb.GO: It makes sense. It’s like any trend, really. Even if they’re as versatile as we’ve been propping them up to be, loafers reached an inflection point where, for some guys, they’re just not the vibe anymore. But I don’t think they’ll dip so low to be thought of as cringe or as an emblem of the 2020s. They’re as classic as it gets and they’ll go through their own ebbs and flows.A hypothetical scenario: You come across an item that costs exactly one cent, and the only money you have on you is the penny in your shoe. What would you buy with that penny?TC: A quarter to increase my net worth 25-fold.GO: A house.