A Lesson in Buy Once, Cry Once: My 8 Year Old Penny Loafers

Sometimes it pays to pay a little more.

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As a card-carrying prep, I’ve come to understand that no wardrobe is complete without a pair of oxblood penny loafers. What makes the penny loafer a sartorial staple is that it looks keen with damn near any casual, smart casual, or business casual outfit you can throw together: Jeans and a t-shirt, chinos and a button down or a henley, hell you can even rock penny loafers with shorts and no-show socks.

To be clear, I’m not talking about the square-toed, elongated, European-styled wonders that look like a cross between clown shoes and slippers. American penny loafers have a round toe, a leather sole, and a beefroll for a little flare (That’s the little roll of leather on either side of the strap. Oh, and the strap is the part that holds your penny. But don’t actually put a penny in there unless you’re seven-years-old or you’re Andy Bernard).

Anyway, the American loafer as we know it was actually developed by a Norwegian designer and was subsequently made popular in America by G.H. Bass, who introduced the Weejun (get it?).

About eight years ago I’d worn my Weejuns into the ground: the stitching was coming apart, the insole had all but melted away from bare-foot wear (I didn’t know about no-shows), and the leather simply hadn’t aged well after two winters. I had just finished my master’s degree and decided I was going to treat myself by going a step above the Weejun.

Buy Once, Cry Once: Refers to paying more money for a product of higher quality up front, instead of having to continue to pay for the replacements of cheaper, lower quality options. Depending on how much you'll use something, buying the higher quality but more expensive option can be cheaper in the long run.

I scoured the internet, read reviews, and had it whittled down to a few choices. Then I talked to my friend, Kurt, who’s from New England (Kurt’s a true prep). He said, “If you’re looking for a new pair of loafers, Alden is your only choice.”

I’d heard of Alden, but they weren’t actually on my list, so I did a little research. Alden is one of the last remaining American shoe companies. Alden makes shoes out of genuine cordovan leather. And Alden makes the famous Indy Boot (the boot that Indiana Jones wore in the movies). Yeah, ok…Kurt was right.

Mike Henson wearing white henley, green chinos, and brown penny loafers

After eight years of hard wear, I still have my Alden penny loafers. The leather is creased, the insole is worn down, and the outer soles and heels have been thrice replaced. But they’re still kickin’. See, the Weejun is a great shoe, but if you want longevity, I firmly believe that you get what you pay for. And with shoes, sometimes it pays to pay a bit more. I’ll take some credit: I use high-quality shoe polish and a custom-made shoe polisher that can reach every crevice and stitch, but in the end, Alden’s craftsmanship and artistry get the glory.

person using a shoe polisher machine to polish penny loafer shoes

Spending $50-100 on your shoes is no small sum, but if you’re able to make the stretch, the $300-400 range opens up a world of quality and enduring character that may be the step up you’ve been looking for. The model I own has been discontinued by Alden but they have others.

Here are a few loafers to consider…