It is MIGHTY hard to not wear socks with loafers and not veer too prep. No knock against prep, but if you are moving the needle in the Ivy direction and you want to wear loafers and no socks, you probably default to the traditional penny loafer, with its unfortunately named beefroll, wide slot for pennies, and traditional sole. I know I did. Looking back, I realize now how fraught that was, how close to a gingham spread collar shirt with shorts I was. But I see it now.
It is trying too hard. Ivy is irreverent, but always with at least one hand on the wheel. No socks with traditional loafers looks to me like wearing a tie with no shirt. I mean, you CAN do it. But you oughtn’t. The traditional penny loafer is a fall/winter shoe, you want wheat socks, or white socks.
By the way, the penny loafer is so named because… back in the day a phone call on a pay phone was two cents. If you amortize my cell bill, my daughter’s calls come out to about two cents each as well, but only because there is a monthly tally of over a million of them. Still, it is nice to see a tradition continue, right?
But that form. The vamp, the wink towards formality. The penny loafer in structure and aesthetic is exactly pure Ivy, always a dose of tradition and formality, but done by integrating the other values, dignity, appreciation for the value of work and thought, etc. How do you leverage that form, the fulcrum between relaxed and appropriate, without using too much product to slick your hair back?
I found the answer. The Jay Butler Loafer. You can check it out here. (that’s the one I have, it comes in different widths and colors) (and that’s a link, thank you very much – I don’t always include links in the Ivy Notes pieces because by the time you switch back and forth between the four or five things we cover in those, you get Ivy fatigue)
Why is this the answer? Three reasons.
I was afraid of the sole. It is a thinner sole. I had a pair of Sperry driving moccasins that lasted maybe a couple of weeks before I wore the sole out? There is no such thing as an attractive picture of the sole of a shoe after three weeks of wear, so for this, you must take my word. The soles are thin but sturdy, you do not feel like you are walking in a shoe you can’t walk in. Justin Jeffers, the founder of Jay Butler shoes, is as much architect as he is anything else, and he has found a way to make a lighter weight loafer wear like one with soles three times as thick.
Second. No socks is, not to put too fine a point on it, as much of a challenge for the inside of a shoe as the ground is for the outside. Perhaps moreso. Here is what the inside of my loafers look like after pretty much every day wear for three weeks.
I cannot tell you how, but I can tell you THAT Jeffers has built a non-synthetic loafer that looks like it is going to outlive me.
Third, the design. I have discovered after about three days that there is no such thing as a photo of me trying to show you shoes in different clothes that isn’t… off putting. But the design is versatile. I know Jeffers (smartly) markets these shoes as more casual, and of course, jeans, khakis, 100%. But they also go well with slacks. Here. None of these came out good, but this gives you a sense of what they look like with slacks:
While Jeffers does hold the secret of how these shoes hold up so well close to the vest, he does give you a few tips as to why these shoes are so unusual. They are not constructed like loafers, they are constructed like moccasins. THAT’s why they feel the way they do. There is a way they are stitched, and they are handmade by Cordwainers (just buy them because Jeffers knows the word “Cordwainers”) in Leon, Mexico. Wanna see how they are made? Click here.
Finally, let’s talk money. These shoes cost $195. They are gonna last, that you know. But what you may not know is what kind of savings that is. Valesca’s Meister (with that jagged tongue thing?) – $295. The Rake’s Barbenera (closest comparison I could find in look, but still does not compare in feel… Jay Butler are moccasins for crying out loud) – $450. That’s more than double, if the math isn’t speaking to you yet. Gucci Penny Loafers – if you shop hard, you can find them at $880. Jay Butler… $195. Did I mention, moccasins?