The Weejun, resoled and in action
Some years ago now, while looking for information on suits, I stumbled on the Ask Andy About Clothes forum and an obsession was born.
There are sub-obsessions, and for the last two years mine has been finding the right penny loafer. I was loafer-resistant: the concept seemed pretty sissified to me, and I still won't even consider a tassel. Very gradually I warmed to the idea of a loafer at all via the boat shoe. From the battered Topsider it's a fairly short stretch to the Weejun, the famous penny loafer made by Bass.
I tried a pair from the outlet store in Lee, Mass. My first mistake was buying them too big. I was under the impression loafers should be the same size as one's other shoes. Maybe for other guys, but not me. I need one that is shorter, otherwise it just flops around.
The second mistake was buying the Weejuns from the outlet at all. The typical Bass loafer available at outlets is made of a shiny (and, I learned, cheap) leather called corrected grain. It looks like plastic and feels like it, too. I eventually thrifted a pair of older USA-made Weejuns with the soles falling off, and had them resoled by an outfit called NuShoe. (Oddly, the uppers and interior were fine.)
Back to the forum. I read up on loafers, and the odyssey began.
I discovered that Lands End shoes run big, like their sport jackets. I discovered that the penny loafer as practiced by whoever makes the calfskin ones for Brooks is too pointy. I found that Sebago's corrected grain isn't nearly as obnoxious as that used by Bass, and that by combining black loafers with baggy chinos and a plaid short-sleeve sport shirt with a button-down collar one can recreate the look sported by the young Richard Dreyfuss in American Graffiti. (Not that it comes up often, or ever, but nice to know the option's there.)
And I found it gets tricky when one has a skinny ankle and a wide-ish everything else. I can get the heel right and have too much up front, or it can fit like a glove in the toe box and I'm falling out of them in the back.
But I persevered, and experimented, and spent too much money, and now I have a bunch of penny loafers that are satisfactory or better, to varying degrees.
Sebago Cayman flat-strap penny loafer
The best of them are...
With socks - Allen Edmonds Hanover, Sebago Cayman in brown
Sans socks - Quoddy Trail Company Pennies with camp sole, Allen Edmonds Lawrence with lug sole
Cool - AE Hanovers, black Sebago Classic, Sebago Cayman
Pleasantly stodgy - Bass Weejuns (thrifted pair, resoled, much better leather), Sebago Classic in brown
Strictly utilitarian - Bass Logans, the oiled leather Sebagos, the Quoddys.
Different league - AE Randolphs in shell cordo (I think).
Story behind these - got them on eBay, and noticed the leather just seemed more substantial than anything else I owned. Then I took a spill and managed to scratch the hell out of them. Ruined, I thought. Shoe cream, polish, leather conditioners - nothing helped.
Then I read up on shell cordovan and learned that the oils in this type of leather stay put forever. Should some calamity occur, the best bet is to give the shoes a brisk brushing and leave them alone to allow Nature to take its course.
Which I did, and now the scratches are barely noticeable. (Which is why I think these are shell.)