I love loafers. I love penny loafers, I love tassel loafers, and love that you're interested in both, Bennett. You bring up a great (and not easy!) question… when to wear which ones?
On the surface, the shoes seem to do the same thing, but there seem to be two very distinct camps: "tassel guys" and "penny guys." In my experience, it seems that penny guys think of tassels as too novel or decorative – too much flourish. And to the tassel guys, the penny loafer can seem dressed-down or staid, like maybe it's missing something. For me, both versions make my list of the 5 dress shoes every guy should own. And for a lot of great reasons.
In more relaxed settings, the short answer is that they're interchangeable. Wear either with jeans, khakis, dress trousers, and pretty much any 5-pockets, like corduroys. Plus both pennies and tassels party well with sport jackets – with or without ties – sport shirts, sweaters, and polos. Again, pretty broad set of possibilities here.
Now, once you start veering into suit territory, things get nuanced. So before sporting a suit with loafers, I like to consider all elements at play, rather than just the tassel vs. penny distinction. Are they Italian or American? Calfskin or suede? Socks or no socks? What's the setting? All communicate slightly different degrees of formality, depending on the type of suit you're wearing. So here are my rules…
In terms of MAKE. Shoes made in England or in Italy can tend to lean dressier than a typical American (handsewn) loafer, Alden notwithstanding. We have a fantastic American penny loafer, which goes real casual real quick… especially in light suede or a Scotch grain. It's got that traditional moccasin toe and the imperfection gives it an easier feel. There's kind of a knockaround vibe to it. On the other hand, our Italian penny feels much sleeker and more refined. This really shines through with the stitching, the leather, and the profile of the sole. So with a suit I'm sticking with Euros, tassel or penny.
For MATERIALS, calfskin (or shell cordovan) is best for dressier suits like sharkskin, and if I'm on the formality fence, I probably would wear them with socks that match my trousers. On the flip side, suede is going to casual-ize the look a bit by adding some texture, and is best for crunchier, less formal suit materials (high-twist wool, for instance) or more seasonal fabrics, like a flannel or a silk-linen. And oftentimes I like to go sockless with suede. Below is a rough spectrum of how we like to think about the tassel vs. penny breakdown… as you can see, it's not quite as much of a binary as you might think. (For simplicity's sake we limited the options to our assortment — we only make tassels in Italy — and skipped the question of socks, which would have added another six data points, and which automatically make your look dressier.)
On the whole, I find that a tassel loafer, even though it is a little more playful or adventurous, is also more refined, and works better with suits than a penny loafer does. The penny is more utilitarian. And with a suit, it can be a cool look! You just want to think about all of your outfit's ingredients before totally going for it.
The beauty of both of these shoes is that outside of the most formal of occasions (black tie, or maybe a super-serious boardroom) you can pretty much wear both almost any time. I think it sort of comes down to your personal preference and the silhouette. I'm more of a tassel guy these days – as are most of the guys in our shop - but ask me again in a few months! I dove a little deep on this one, but you really can't go wrong… and hey, both look good on the pedals of a bike.
If I were you, I'd try 'em both on, and just trust your instinct.
