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.