Edition 22: The Perfect Penny Loafers

A desperate request for holy grail footwear

Greetings, friends! And welcome to Caroline Finds It: my weekly newsletter where I reply to submissions from YOU for objects and products you need recommendations for.

I’ve got a long-form deep dive into the Wild World of Penny Loafers for you today. From Julianne in Brooklyn, whose submission is too wonderfully descriptive to not share verbatim:

“Dear Caroline of Caroline Finds It,

My query seems so basic — comfortable and decent quality real leather Penny loafers — but you wouldn’t believe the trouble I’ve had tracking down a pair for myself. I’d like something neither too polished nor refined. No need for a high gloss on them or for pointy toes either. The kind of shoes you could imagine wearing with slacks or jeans, with a classic, slim profile and ever so slightly masculine edge. No flashy hardware, no chunky heel. The kinds of shoes you could slip on and spend a weekend in. 

My primary problems are that I seem to have a wide toe box but a narrow heel, so even ordering the correct length in wide width shoes is no good. At this point I’ve bought too many cheaper options, hoping they’d be fine enough. But oh they’ve been duds. Too stiff and ill-fitting, even after a lengthy breaking in, and pinchy in one spot but loose in another. Where am I not looking?

My real dream loafers are Church’s but I haven’t got the budget for $1,000+ shoes! Though at this point I’ve already spent at least 25% and been disappointed by multiple cheaper brands, including Eastland and J. Crew. 

Help a girl out!

Yours in loafer love,

Julianne

P.S. to add to the pile of duds, I've tried on Cole Haan, & Other Stories, and about a year ago when I last looked it seemed like Bass Weejuns were no longer available. Maybe they’re back? I’d take a classic Weejun if it could fit me!”

Dear Julianne,

There is a loafer out there for you!! I wish more people put more thought and care into their everyday shoes. Kudos to you for embarking on this journey! It’s absolutely worth the effort. Our feet carry us through our every day lives and bear so much of the burden of our physicality and deserve more love than we often give them. Well-fitted, quality, cared for footwear is the first step.

Before we dive into some options for you, how about a brief history of the penny loafer?

Legend has it that the penny loafer was first made in the 1930s. Back then, a call on a pay phone cost 2 cents, so the point was that each shoe securely held a penny so you always had what you needed to make an emergency phone call.

G.H. Bass Weejuns are credited for being the first, and were introduced in 1934. The shiny oxblood Weejun ushered in the penny loafer revolution of the 50s and 60s when they became a hallmark of preppy style but by then, pennies were replaced with dimes for payphone use.

In very recent history, there’s been a lot of restructuring within the century-old G.H. Bass company as they’ve traded in their beach town outlet mall shops for a more upscale offering on their online store. The Weejun has been given a new life and has weaseled its way back into mainstream fashion.

When I was in college, I was in the habit of buying a fresh pair of Weejuns each year, as I had no idea how to care for them and one year of regular use left holes in the leather soles and the heel sagging. My starkest memory from this time was the pain that the break-in process caused. One week of bloody feet was worth a whole year of easy but stylish footwear. And yes, I did put actual pennies in mine because despite the general preference to omit them, it’s part of the charm, in my opinion.

I have no doubt that you’d be perfect satisfied with the recently re-vamped Weejun for a reasonable $155 with a little bit of cobbler intervention, especially because it comes in great colors which you could collect over time. But that’s not why you’re here — you’re here to find something that you don’t already know about. The shoe that is just for you.

The most important thing when buying shoes is to know your foot as well as you can! Are your feet wide? Do you have high arches? As we know about Julianne, she has a narrow heel but a wide toe box. All of these things affect how your shoes are going to feel and how difficult they’ll be to break in. Julianne, in your case — have you tried buying something that fits your heel and then stretching the toe box? Your local cobbler can help you with this, or you can find many techniques to try online. That’s a much better solution than putting adhesive pads in the heel, which will just get sticky and gross and likely not stay in place for long.

I can’t guarantee that any of these will fit you perfectly out of the box, but they’re worth a try, and are high quality enough to be worth sending to the cobbler over and over again. One thing I tried to look for was loafer models that appear to be core styles of the brand that makes them. Nothing is worse than finding your holy grail shoe only to have it discontinued after two seasons.

Scarossa makes gorgeous loafers in numerous styles including a slim, sophisticated penny loafer (the Valeria, as pictured below) and a chunkier more casual version (the Harper). Both are $345 and made with care in Italy. I love these for you because they’re so clean and modern, and also appear to be made from leather that is softer and thus easier to break in than the thick, glossy standard.

Rancourt & Co. shoes are made in Maine! Their Somerset loafer is classic, and affordable at $275. They do make custom shoes at not-totally-outrageous price-point, so if you like the shoe but the fit isn’t quite right, you could inquire about having one made to your exact needs. I think you’ll like this one in classic penny loafer oxblood, but without the sheen.

Tod’s is a brand that’s synonymous with driving moccasins, but their more polished loafers are just as lovely. These ones are a little chunkier than the others, but their grippy rubber soles will serve you well during NYC winter and their special Tod’s coins are a cute touch. At $675, they’re pricy, but likely worth it.

Frēda Salvador makes the sassiest pair I've chosen for you, with cheeky details like the notched welt, and curved heel. They’re $375 and one of the more interesting and less silly-looking “fashion” pairs I’ve encountered. It appears that the toe box on these may be a bit narrow, but it’s hard to tell unless you try them on.

A few wildcards for you:

Paraboot is a lovely French heritage brand that is really really hard to find in the US but is worth seeking out if you ever find yourself traveling in Europe! They have a couple of models I think you’d be interested in.

Céline currently has these deliciously soft looking black beauties, which I’m finding a hard time resisting the urge to purchase.

Maryam Nassir Zadeh is a cool girl go-to, and I was surprised to find this wildly fun periwinkle pair with a stylish slightly square toe.

Notes on loafer maintenance:

If you are a city dweller who spends a lot of time of your feet and buys shoes with a smooth leather sole, PLEASE be kind to them and take them to the cobbler to have rubber soles put on before you even wear them out of the house for the first time. Trust me. They’ll look just the same, last longer and keep you from slipping.

In addition, be sure to inspect your frequently worn leather shoes monthly to make sure that they’re cleaned, conditioned and not in need of a new heel or toe tip. Depending on how you walk, different parts of your shoe will wear down more quickly than others and it’s much easier to fix if you catch it before it gets into the leather structure of the shoe.

In lieu of a favorite product of the week, I would like to share my personal footwear story:

An Ode to the Gucci Loafer

When I first laid eyes on the new version of the Gucci Loafer, named Jordaan (pronounced Jor-dAHn) I was in line behind a very chic woman on intake day at New York County jury duty in 2016. I thought to myself — are those real? Did this woman really wear Gucci loafers with floral print sweatpants to jury duty? How do I become her?

After two years of lusting over a red pair, I was gifted them for my birthday. My very own pair of magic ruby slippers. When I opened the box I was in awe of their craftsmanship and the perfect cherry red of their buttery leather. And then I tried them on. To my horror, my food wouldn’t even go halfway in. Nearly in tears, we took the shoes to the shop and the shopgirl asked me if I’d tried using a shoe horn. Aren’t shoe horns for men’s shoes? I though to myself. She whipped one out of her pocked and handed it to me and voilà — my foot slid right in and I knew within 20 seconds that I’d found my holy grail: a shoe that fit my foot as if it was custom made for me.

I wore them nearly every day until my next birthday, when I decided to buy myself my own pair in a different color. Since then, I’ve begun a tradition of the “birthday loafer” and have grown my collection of my favorite footwear into a rainbow row in my closet. Though the experience of going to the Gucci store is divine, most of the pairs I own were purchased secondhand, but in mint condition, for half the price from websites like Vestiaire Collective and good ol’ eBay.

What I’ve learned from my beloved Jordaan is: it pays to buy less, but to buy things you actually will wear and feel comfortable in. Take care of them as you would anything else that you love and they’ll reward you with years and years of service to your body and personal sense of style.

So Julianne, start trolling the sites for a deal on your dream Church’s. You never know what’s you’ll find.

Is there a product you’re looking for? Submit your request here. See you next week for fresh recommendations! xo Caroline