Tassel vs. Penny: What Kind of Loafer Are You?

The men behind Gilt MANual answer your most pressing style questions.
Photo: Take Ivy

Preppies. In Pennies. At Princeton (circa '64).

Tassels or Pennies? I am in my 20’s and can’t choose between them. Which is better?

The short answer is: Yes, definitely. Both styles of loafer are great options, no matter your age.

The longer answer, my friend, is something of an existential exercise. Just as an artist must find his voice within the context of his craft, every man’s gotta find his sartorial sweet spot; and these types of questions are precisely the way to refine your overall vision. Put bluntly, are you a tassel-y type guy or a penny sort of chap? Or both?

Myself, I’m rather more conservative in these matters and tend to err on the side of smoother lines—ergo penny.  Which isn’t to say I’m scared of a couple of flopping bits of fringe on the top of my foot. I’m not ruling either out, and I’m okay with that. The decision, for me, will ultimately come down to a specific shoe, case by case.

And though you are young, you are living in a very exciting time for men’s style, with range of availability and access to good swag at an all-time high. Entire back catalogs of great shoemakers are a click away, as are rather affordable custom and M2M options; not to mention a ridiculously high bar of quality for your average, store-bought, ready-to-wear loafer. You could, for example, collect an entire flight of Ferragamo slipons off eBay (in infinite variations, from moc toe to kiltie; in croc skin, cordovan, or suede; on flat soles or heeled; as penny, tassel, or driver) were you so inclined. There’s no reason you can’t try out inexpensive versions of both styles (found in thrift stores or, you know, on Gilt MAN) while deciding on a favorite.

That being said, the enduring classic Gucci slide is never going to go out of style and might be the perfect gateway loafer for you. ‘Round these parts that type of thing is what we call an essential, and a cornerstone of any great shoe collection. I’ve got a pair in my stable (as I daresay do most, if not all, of my colleagues), and I must admit, all this talking about loafers has me on the hunt for another one. I’ll race you to a new pair. Ready, go.

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  1. null says:

    what’s your take on penny loafers “must” be worn with socks?

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