I have a lot of shoes. Many of them were acquired during my years of work for a place that may be described as a “foot locker” of sorts, but even after my departure for greener pastures, I still find footwear (of the sneaker-ish variety) relatively enthralling.

As a result, I don’t tend to wear any given pair a lot, and so they all reach a point of looking somewhat worn but not completely broken before I move on to the next thing that catches my interest. And that’s why I’m confounded by a pair of Vans I bought 5 years ago.

When I first started wearing the Slip-Ons, I was somewhat skeptical. It’s not that they were uncomfortable by any means; more that I wasn’t sure if I liked how they looked on my feet. But I quickly acclimated to the sight of that solid white strip of sole, and the Vans became my go-to shoes. They’ve been with me to Chicago and Vegas (among other more local places), rehearsals and performances, work and play, and they’re one of the few pairs of shoes I have that remains consistently stylish (I believe the word is “classic”) regardless of what they’re paired with.

It soon became clear that I had found a staple to my wardrobe; I wore the Vans more frequently than any other shoes. Like a great pair of jeans, they got more comfortable and better-looking with age, each little rub and tear adding to a perfect patina. But, paranoid as I am, I knew they wouldn’t last forever, and I knew that I’d want to have a replacement on hand for when that time came. My first second pair of Slip-Ons were the vaunted checkerboard colorway, which were soon joined by a cappuccino pair (both on sale, so why not?).

The thing about Slip-Ons is that they get better with age – the blackened sole, worn down logo on the heel, the weathering of the seams. So when presented with a choice between unbroken new shoes or perfectly-worn not-new shoes, I almost inevitably choose the latter, which is why both of the other pairs are still relatively new-looking. I’ll be honest: I think brand new Vans look a little goofy; it’s only after they start to wear that they look like they should. The problem is convincing myself to push through that goofy phase (it’s kind of like when your hair is too long to be short but too short to be long) instead of just wearing the other pair of shoes that I already like.

But I’ve been feeling for awhile that my favorite pair has been close to critical mass. They’re not as bad as they could be, but it’s time to transition them to semi-retirement status. Fortunately, I think I’ve lined up a suitable replacement (for real this time), and so the cycle begins again.