Which Penny Loafers Should You Buy?

Loafers come in all manner of styles from tassel to Venetian to Belgian, but perhaps the most enduring style with the broadest appeal is the penny loafer.

Originating in Europe, the moccasin-style loafer made its way to the States in the early 1900s. It was adopted by traveling Americans who brought the style back with them to their college campuses where they would pair them with white socks and shorts, chinos and jeans. As for the currency moniker, that was a result of the Ivy set decorating their loafers with pennies inserted into the straps.

If you’re looking for a pair of pennies for yourself, you might be looking at the G.H. Bass & Co. Weejun. The brand introduced it in the 1930s and is responsible for making the style famous. In its wake, countless others tried their hand (or feet) at the style, not the least of which is premier American shoemaker Alden. Their 986 Shell Cordovan Leisure Handsewn Loafers have been praised by menswear aficionados for its quality and style over the decades, making it a staple in a discerning wardrobe. But which one should you get? We compared the two side by side to see which pair is the pair for you.

G.H. Bass & Co. Weejun

Price: $110

Materials: The Weejuns feature a leather upper that is fairly pliable and has a decent sheen to it. The leather itself is a corrected grain leather which is how it gets its sheen.

Construction: As far as construction, the Weejuns are unlined and use a blake stitch technique that stitches the uppers directly to the outsole.

Design: The Weejuns are a classic beefroll penny loafer, named after the stitching at the strap across the top of the shoe where it resembles a cut of beef tied with butchers twine. The toe features moccasin-style stitching and is neither aggressively pointy nor too stubby.

Sizing: I usually opt for a EU41 or a US8.5. However, the sizing of the Weejun is smaller and, while the pair we tried was a EU41 / US8, I needed a whole size up to a EU42/ US9.

Alden Leisure Handsewn Shell Cordovan Loafer

Price: $732

Materials: The shell cordovan upper is absolutely gorgeous. The so-called Color 8 shade of Horween’s infamous cordovan starts out a deep, dark burgundy before giving away to lighter tones and even shades of walnut. It’s tough to break in compared to many shoes and especially paired next to the Weejuns.

Construction: The construction of the Leisure Handsewn loafer is great. It features a Goodyear-welted leather sole with decorative fudging, a leather lining and insole, a cork filling and a steel shank for stability.

Design: Alden’s penny loafers are more refined and sculpted than the silhouette of Bass’s iconic Weejun. They feature a flat strap with a simplified penny cutout. If the Weejun is the icon, Alden’s might be its fraternal twin.

Sizing: Alden’s 986 is a bit wider and my feet fit well into the size 8. For reference, I wear 8.5 in Vans and an 8 in Red Wings.

Which One Is Right for You?

Bass Weejun: The Bass Weejun is the prototypical penny loafer. The design, the silhouette, the name — you can’t get much more authentic than this. It’s more lightweight, more flexible and more affordable than most other pairs.

The construction isn’t anything that will stand out in a shoemaking competition (yes, those exist), but you can still have these resoled. It won’t go as many rounds as a Goodyear-welted pair, but will go a few more than a glued sole. The story is the same with the upper. The corrected-grain leather starts out nice enough but won’t age as well as other uncorrected, full-grain leathers.

Sure, you get what you pay for. And in this case, it’s a fair amount.

Alden Leisure Handsewn: It’s hard to compare a shoe that’s literally seven times as expensive as another shoe. You’re asking for Manny Pacquiao to go toe to toe with a random pedestrian. In terms of construction and materials, it’s no contest. Because of the construction and materials, it’s not just heavy on the wallet — it actually has some substantial heft — and the formidable break-in period can be a turnoff for many.

That said, if you’re looking to have a pair of penny loafers that will last you over a decade, these are it.

G.H. Bass & Co provided this product for review.

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