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Penny Loafers – Five Plus One

Five Plus One is our weekly series of buyer’s guides. We pick a specific category and dig up five great options along with one that’s a little outside the norm.


When penny loafers hit the market in the late 1930s, it cost one cent to make a call from a payphone; it wasn’t long before people began storing pennies in the strap of their loafers, and the true penny loafer was born. From the 1960s to the 1980s, penny loafers really began to surge in popularity — from American prep to being worn with a casual suit, penny loafers were (and still are) everywhere.

Their versatility is one of their best features, not only in terms of formality but in terms of design as well. While classic penny loafers will always remain popular, the design is open-ended enough for different companies to modify their shoes to be truly unique. From sole type to construction method, and from leather type to sole design, it’s astounding how many cohesive penny loafer designs are available today.

1) Carlos Santos: Suede Penny Loafer

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First, is a pair of Suede Penny Loafers from Carlos Santos. This pair is about as standard as they come: brown suede, leather sole, tonal stitching, and a traditional round-toe last. They are constructed using 270-degree Goodyear Welting, and feature an understated strap across the top of the foot.

Available for $325 from Skoaktiebolaget.

2) Edward Green: Duke Penny Loafer

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For those of you who just want to skip ahead to the best, look no further than Edward Green. Their Duke Penny Loafer checks just about every box imaginable. Immaculate stitching, beautiful leather with excellent depth of color, wheeled welt, and oak bark tanned leather soles for maximum durability. Their designs are well refined — even the ornamental design on the strap is more elegant than their competitors. Their attention to detail doesn’t come cheap, but it’s nice to see what the top end of the market has to offer (even if for nothing more than reference).

Available for $1255 from Mr. Porter.

3) Quoddy: Penny Moc

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It can be nice to get the instant gratification of picking up a new pair of shoes, but sometimes it can be worth it to wait for the specifications that you really want — and with Quoddy’s made-to-order program you can do just that. With twelve different leathers to choose from, four colors of thread, four types of soles, and five colors of inner lining, you have your work cut out for you in terms of design. This style of penny loafer is a bit less traditional than some. The wrapped wedge sole gives these loafers a much more casual, campy look but doesn’t fully diverge from traditional penny loafers.

Available for $325 from Quoddy.

4) Alden: Penny Loafer in Black Chromexcel

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Alden is one of America’s classic shoemakers, and as such their traditional designs are spot on. Their Penny Loafer features moc-toe stitching the same way that their Indy Boot does, 360° Goodyear Welting, and their flexible leather sole. In all honesty, I’m not usually a fan of Chromexcel leather; however, seeing as Penny Loafers are traditionally worn without socks, I think that CXL leather is going to offer an incredibly comfortable walking experience — just what you’d want from a loafer.

Available for $530 from Unionmade Goods.

5) Heschung: Suede Penny Loafer

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I’ve been becoming more and more enamored with Heschung over the last several months — maybe it’s the interesting proportions that their shoes always have or perhaps just their novel designs in general. Whatever the reason, their Dark Brown Suede Penny is one of my favorite loafers on the market. With its higher than average heel cup this shoe gives the appearance of having a higher heel than it does, which makes the entire shoe appear to taper at a very interesting angle. It is constructed from calfskin lined waterproof suede, and features 270º Goodyear Welting.

Available for $347 from No Man Walks Alone.

Plus One – Hender Scheme: Slouchy Loafer

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Although mostly known for their sneakers, Hender Scheme has been furthering their non-sneaker offerings as of late — and the products they have released have been phenomenal. This penny loafer is quite different from the competition. It is made of an undyed veg tan so it will darken with age, and it features a Norwegian Split Toe rather than a traditional moc toe. Add in the stitching on the back of the heel and the heel’s lowered height, and you have one truly unique penny loafer.

Available for $579 from Blue Button Shop.