New Penny Loafers from Jack Erwin

With summer fast approaching, I was in the market for a simple, handsome and elegant slip-on for casual wear. I thought about loafers from Alden and Tods, but an easy everyday shoe that I’d be wearing for walking the dog didn’t strike me as an occasion to splurge. Then I remembered Jack Erwin.


The Archie Penny Loafer from their Sullivan Collection was perfect. Very similar in design to penny loafers from Alden and J.Crew, the Archie had a great-looking shape and silhouette with a Goodyear construction, a full-grain calfskin upper, a full leather lining with a padded insole, a hand-stitched leather outsole and a reinforced stacked heel. Price: $195.


Since I already have a great pair of brown loafers from J.Crew, I pulled the trigger on an alternate pair in black. A few days later, my new black penny loafers arrived. I immediately brought them to my local cobbler for rubber under the soles and taps on the heels.

After wearing them every other day since I got them, they’ve been breaking in nicely, looking great and feeling fantastic. Affordable, handsome, well-made and workable black loafer problem solved.


  1. They look beautiful. What made you decide to do rubber under the soles this time?

    • George Reply

      I anticipate more walking in these. I also wanted to try the rubber option to see if it is preferable to a front tap in any way.

      • Let us know what you think when you come to a conclusion. I enjoy the air of confidence I get from the feel and sound of the Goodyear welt, but there are times I’ve wanted to make a quieter entrance. Maybe the rubber is just what I’m looking for.

  2. I have wanted to purchase (on-line) a pair of Jack Erwin loafers for some time but I have heard/read conflicting reviews regarding the QUALITY of the leather uppers. When I hear “for the price…” red flags go up (I usually wear AE, Bally, Santoni and Testoni’s). I’m sure the construction is fine, but how is the leather, how does it LOOK and FEEL?

    • George Reply

      I addressed the same issue in my original review of the line:
      The simple reality is that one simply cannot get Alden-quality Horween leather and superlative craftsmanship in a $200 shoe. In our “Get it cheaper/get it faster” consumer culture, something’s got to give. For many guys looking for an affordable and well-made option, the leather upper is “good enough.” As you’ll read in the original article, the leather quality isn’t brilliant but it’s not dissimilar to designer shoes I’ve seen for two and three times the price, and it’s definitely an upgrade to the dress shoe leather I see on most men’s feet in NYC.

  3. Seems like a great way to look stylish even when you’re lounging … might have to buy a pair!

  4. George,
    A little late to the party, but my Archie Penny Loafers just arrived and I’m very happy. Solidly built. Very affordable. And my first pair of shoes with a proper Goodyear welt! There’s no going back. Question: they are my correct size but very tight. Is this normal?

    • Thanks, Doug! Wear mine all the time. If they’re too tight, maybe return for 1/2 size up? If memory serves, they’re very reasonable about exchanges.

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