Lamenting On Downed Wingmen…

Lamenting On Downed Wingmen…


It happens every few years.  And when it does, I am an emotional wreck.  That is, when I admit to myself that my go-to Sperry Top Siders ought to be retired and enshrined in my memory for the times they accompanied me for the best of nights at the Box, epic road trips, legendary concerts and other general tomfoolery and ruckus.  Now, this decision is not an easy one and I procrastinate making it more than I did writing any paper in college or high school. It gives me separation anxiety, at a minimum.

My general rule of thumb is to retire them only when I fear they may fall apart on the next wear, or in this case, when my feet run the risk of touching the New York City sidewalk; which is a horrifyingly unsanitary thought.

My current Top Siders have had holes in the big toe part of the sole for about a month now.  Additionally, the sole is no longer attached to the upper around the big toe.  Sloppy, some would say.  No.  They are just lived in.  They are still wearable.  The frugal side in me kicks in; then there’s that, you know, whole prep ethos of the older the better…  The shoes have a story, a personality, a past, a present; but sadly, an unfortunately short future.  They are now flawlessly accustomed to the presence of my foot; and my foot to them.  When I put them on it just feels so right.  I ask myself, will I ever find a pair as good as these again?

I’ll let you know in a few years.


  1. I am 30. I *just* retired a pair of sperry topsiders that I had had since I was 17. They still had pen drawings on the side of the sole that a friend of mine did when we were bored in Calc class senior year of high school. I had them stitched up once or twice by an elderly shoe repairman who told me that they weren’t worth fixing. (PS — Yours look positively pristine compared to the condition mine were in).

    • Matthew,
      That’s awesome. My mom has had the same pair for a few decades as well. She doesn’t wear them near as hard as I do, however. Last weekend I was at a graffiti exhibition in Long Island City and had two of the artists draw on the shoes, now they are wearable art, although I doubt I will wear them going forward. I’ll post some pics up sometime soon.

  2. Boat shoes are overestimated. If you wear them more than a couple hours walking or at concert they just kill your feet. They are good only for the boat and the beach.

    • You obviously haven’t found the right set then, I can, and do, wear mine all day every day. As the post above said, “They are now flawlessly accustomed to the presence of my foot; and my foot to them.”