You know the loafers you wore to work all summer? The vaguely Italian-looking, slightly elongated numbers that most likely appear in some light shade of brown? The ones you even deigned to wear without socks a few times? Yeah, those. They’ve had a really solid four- or five-month run — now put them in the back of the closet and consider a more seasonally appropriate alternative: the burgundy penny loafer.
The original iteration of the shoe, the Bass Weejun, turned up on campus at Yale University in the late 1930s and has ever since been a cornerstone of the traditional Ivy League — eventually known as "preppy" — wardrobe. JFK wore them. Holden Caulfield probably wore them before he ditched Pencey. And, yes, your dad probably wore them. Maybe he still does. And so should you.
The way I see it, there are two acceptable versions of the shoe. First, there's what's often referred to as the "beef roll" loafer (above), which, yes, sounds really disgusting! It gets its name from the stitching on the leather at either side of the vamp, which produces a bunched-up little patch of leather that looks very much like a trussed beef tenderloin. This version works well with a pair of dark denim or some slim-fitting chinos that hit just below the ankle — too much break in your pant leg and you'll wind up aging yourself a good 30 years.
The other version (below) is the slightly more elegant leisure handsewn moccasin, which is characterized by, duh, its handsewn stitching around the vamp and on the penny saddle. These tend to be a bit longer and generally less bulky, and thus do better in a dressier get-up. They practically scream to be worn with a nice, thick pair of gray flannels (consider cuffs) and a real oxford cloth button down — none of those silly short-collar abominations everyone's been selling these past few years. If you want to go all the way and add a repp tie and a blue blazer, I'm not going to stop you.
As for your options, well, there aren't actually all that many. If you're interested in the beef roll, you could very well go with the original Weejun ($110), which, it must be said, is of lower quality than the actual original Weejun. The leather feels a bit plasticky, but considering the low price point and the frequency with which they go on sale, they're certainly a viable option. Up a little higher on the price ladder, at a still reasonable $250, you'll find the Allen Edmonds Kenwood. Go up another step from there, and you've got the Oak Street Oxblood at $342.
Should you be interested in the LHS, you've got the Allen Edmonds Randolph at $395 and the Alden Leisure Handsewn 984 at a cool $536. Personally, I think it's too much to pay, at least for calfskin leather as opposed to cordovan. But then again, Alden's cordovan version will run you $692.
A note on socks: You'll be showing a bit more sock than usual due to the penny's shorter vamp, so you'll have to choose carefully. I say it's best to keep it simple. Solids work well as long as you make sure there's some contrast between them and your pants. Subtle stripes are a good middle-of-the-road option, and argyles work as well, assuming you keep the colors at least somewhat muted.
A note on whether or not to put a penny in the slot: You'll have to take a good long look at yourself and make that decision on your own.