Not enough attention is paid to the Penny Loafer as it used to be, or as it should be for that matter. Likely every little boy's first shoe, the American classic has been cast into the shadows of more popular trends, similiar to how women's flats have been given the shaft, becoming shunned to the backs of closets by this season's suede and tassled loafers.
The loafer itself was invented in the 1930s, and during that decade payphones only cost two cents per call. The loafer design allowed just enough space for a penny in each shoe, which was the equivalent of one emergency phone call in a phone booth back then. Thus, the creation of the name, "The Penny Loafer."
They can be pegged as the cliche, go-to shoe for the office, but to me they're timeless. Regardless of how much you may love your wingtips, there's value in investing in a good pair of these... they are worth every penny.
Johannes Huebl goes casual with loafers and colored socks.
1. Allen Edmonds: Westchester in 1647 Walnut Calf. It pains me to look at how expensive these shoes are, but all of Allen Edmonds are made in the USA from a factory in Port Washington, WI. As the website states, just because a shoe is called a Penny Loafer doesn't mean that it can't look like a million bucks (or cost that much!). This one is an investment piece, no doubt, but I love the classic, simplistic look of it.
2. Stacy Adams Serafino Penny Loafer in Cognac. More affordable at a mere $70, but harder to pull off. I think these would go over really well in the South. :)
3. Allen Edmonds: Carlsbad in 6622 Walnut Calf. My favorite, favorite, favorite of them all. The woven detail will attract attention, and while it's primarily a spring/summer shoe, it can easily make its way into the fall with khaki, navy and grey attire.
Clark's Charlie Penny in Cognac Leather: Clarks are the way to go for comfort, although you may have to compromise the uniqueness trait (I'm never completely "wowed" by any shoe they make). This loafer is plain and versatile when it comes to matching, and most of all, pretty affordable.
5. Stacy Adams Nathaniel in Cognac Multi: Like #2, this is a tricky shoe to pull off because of the angled point and two-tone colored detail. This choice is a marriage of Penny Loafer and Wingtips, and shoe that will make a statement, I'd start with the shoes and work the rest of your look from there on up!