I’m a loafer guy. I love them. All sorts of them. I have a disgustingly large collection of tassels, bits, pennies, Belgians, etc. in all different types of leathers. But bringing it home, the penny loafer is arguably the standard by which all loafers are measured.
Penny loafers generally get a bad wrap. Often they are associated with the old Bass Weejuns we wore to church, complete with faces covered in powdered donuts. But they are so much more… There are options that look great with a suit and shorts (bold, but do-able). There are some that are middle 80% loafers, which pretty much work with anything. And there are plenty of casual options. Now, there are plenty of cost-conscious choices out there, but a good pair of penny loafers will never go out of style. If you’re up for it, here are some options to flex:
You won’t find a finer pair of loafers than the Bostons from Crockett & Jones. They are handcrafted in England, feature a sleek, updated last, and the pebbled leather makes these extremely versatile. These will last you the rest of your life.
The Charles penny loafers from Drake’s are a good option as a second pair. The round penny hole gives these a little side-eye, but it looks good. More unique than the normal opening (not that you’d stock a penny). Finish these off with a pair of purple or hunter green cashmere socks and you are in serious business.
These ‘Italian Penny Loafers’ from Sid Mashburn are a great dress penny loafer. These are a smart choice with a suit or with a sport coat (sans socks). They are a taller penny, in that they wear a little more like a structured dress shoe vs. a busted pair of Bass Weejuns.
The Alden unlined penny loafers should be a go-to in every man’s closet. The snuff suede is extremely versatile, and break in extremely well.
And for the over-the-top guys, the American Alligator Jacob penny loafers from Martin Dingman are right up your alley. These are a work of art – the classic penny loafer silhouette but in exotic leather. Pair these with a good pair of jeans or your Sunday best – either way, these will be the coolest shoes in the room.
What are your go-to pennies?
I wear some type of loafer almost every day. For a more casual look (khakhis, ocbd, blazer) I go for the Cole Haan Dustin loafers. These can also be dressed down with shorts, sans socks of course. For a dressier look I stick with the Cole Haan Pinch Penny Loafer. I’ve tried Johnston and Murphys but their quality isn’t there and don’t seem to last long. After seeing them on Ivy Style, I’m interested in a pair from Jay Butler. Does anybody have any experience with them?
I have a pair of Jay Butler shoes. I ordered my usual size, and they have a decent fit. Very thin sole, more like Venetian/Italian than old-school Americana.
I wear cole Haan penny loafers too. I know people say they aren’t as good as they once were but mine work fine.
My go-to is the AE Kenwood penny which has been discontinued. It’s a classic beef roll loafer with subtle pinking to set it apart.
Oak Street Bootmakers Beefroll Penny Loafer in natural is the workhorse of my loafers, I’ll wear them with pretty much anything other than a “business suit” (they’re fine with a “wedding/horse track suit”).
I have a closet full of ’90s vintage Cole Haans, but Alden, Rancourt, and OSB get the most wear.
Alden cordovan LHS 986 No. 8 and the Rancourt cordovan beefroll penny.
My go-to are Allen Edmonds “Cavanaugh”, which I keep spit-shined and are basically my Sunday shoes. A bit more casual than other AE penny options IMO.
I also keep a pair of beef roll Bass weejuns (complete with pennies in the vamp), which are my knock around shoes for when I don’t feel like wearing camp mocs or drivers.
Might not be for everyone, but I made a custom pair of Quoddy Sport Pennys (well 2 pair). I wear these with shorts often.
One the victims of the pandemic for me were shoelaces. I’ve pretty much moved exclusively to loafers (shoes for the gym excluded). I love my suede loafers from Sid, grab those in the snuff and you can wear them almost year round.
Oak Street makes a great natural “daily driver” penny that I wear all the time. OSB also does some custom work, so I’ve picked up a pair of loden (dark green) and a pair of navy that also get a ton of use.
I picked up a pair of Rancourt penny’s in their last crowdfunding/pre-order in natural with the lactea hevea latex soles. If you do a ton of walking, those are a something to look at. Incredibly comfortable.
Alden cordovan LHS 986 in no8 and black. Like to keep the stitches white rather than polish to color.
Also chromexcel beef rolls from OSB
Between a few great brands- little nuisance in fit matters. Nothing broke in for my foot like the Aldens. (I say in past tense because I don’t foresee having to replace them ever.