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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, and 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.

The penny loafer’s versatility is one of its best features, not only in terms of formality but in terms of design as well. While classic pennys 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) Rancourt & Co. : Pinch Penny Loafers

Penny-Loafers---Five-Plus-One-2)-Quoddy-Pinch-Penny-Loafers

Quoddy offers some truly fantastic handsewns, including their Pinch Penny Loafers. If you’re looking for a penny loafer that is incredibly comfortable and low profile, these might be just the ticket. They’re made in Maine from Horween Chromexcel which is comfortable by nature, and when combined with Rancourt’s camp-moc sole and the fact that these shoes are unlined means your feet are in a for a treat as they mold to the aforementioned Horween hide. Available in several different Chromexcel colors, these loafers are a classic iteration of this iconic style and a solid entry option if you’re just starting out with the style.

Available for $265 from Rancourt & Company.

2) Grant Stone: Traveler Penny in Storm Kudu

Penny-Loafers---Five-Plus-One-Plus-One---Grant-Stone-Traveler-Penny-in-Storm-Kudu

Grant Stone has really taken the shoe world by storm over the last few years, and their Traveler Penny in Storm Kudu is just one of their more unique offerings. Made from C.F. Stead‘s storm kudu, these penny loafers are sure to be as soft to the touch as they are unique in appearance. While the leather might be a bit different— featuring natural nicks and imperfections picked up in the East African woodlands — it does nothing to stop these shoes from being worn more formally. Personally, I can’t imagine a shoe on this list that would more fun to pair with some slacks.

Available for $360 ($324 for Heddels+ members) from Grant Stone.

3) Löf & Tung: Shell Cordovan Penny Loafers

Penny-Loafers---Five-Plus-One-3)-Lof-&-Tung-Shell-Cordovan-Penny-Loafers

Landing firmly on the more formal end of the penny-specturm is Löf & Tung‘s Penny Loafer. They’re shown here in the Armagnac colorway shell cordovan, a coveted leather that happens to pair beautifully with the split toe and leather sole chosen by L&T. In addition to untold amounts of lustrous sheen, these Spanish-made shoes feature a full leather lining and a Goodyear welt to make them re-craftable after you’ve flexed them at countless weddings.

Available for €609 from Skoaktiebolaget.

4) Alden: Unlined Penny Loafer in Snuff Suede

Penny-Loafers---Five-Plus-One-4)-Alden-Unlined-Penny-Loafer-in-Snuff-Suede

It’s hard to write an article about classic, Americana footwear without including Alden in the mix — even if the original penny loafers weren’t invented in the states. And while Alden offers dozens of penny loafers we could have chosen, there is something special about their Unlined Penny Loafer in Snuff Suede. The hues and rough texture of the snuff suede balanced with the formality of the leather sole make these shoes easy to pair with chinos, shorts, and jeans alike. Just imagine these dropping with some slubby denim for a snuff ‘n’ slub combo – Nuff said!

Available for $620 from Clutch Cafe.

5) Cheaney: Hudson Penny Loafers

Penny-Loafers---Five-Plus-One-5)-Cheaney-Hudson-Penny-Loafers

Cheaney‘s Hudson Penny Loafers are an another excellent choice if you’re unsure if you’ll be wearing your loafers in an formal or informal setting. There isn’t much to say about the pattern other than it’s a nearly perfect interpretation of classic penny loafers. Featuring tonal stitching, calfskin leather, and a leather outsole, Cheaney certainly weren’t reinventing the wheel with these loafers — they’re offering a great version of a traditional shoe, and there’s nothing wrong with that.

Available for $460 from Leffot.

Plus One –

L.L. Bean: Allagash Bison Handsewns

Penny-Loafers---Five-Plus-One 1) L.L. Bean: Allagash Bison Handsewns

L.L. Bean offers great entry-level footwear and clothing, especially if you’re interested in American heritage-inspired clothing. Their Allagash Bison Handsewns are a great example. These shoes are constructed from American bison leather (including a bison leather insert), with a handsewn moccasin toe and a lugged sole. While the style is quite classic, these penny loafers do feature lacing around the throat, which is a non-standard, boat-shoe characteristic which makes it less classic, less formal, but no less Americana.

Available for $149 from L.L. Bean.

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