Reduce, Reuse, Resole
“It’ll be cheaper to buy a new pair”
Sometime in college, probably junior year, I bought a secondhand pair of Sperry Top-Siders on eBay. I couldn’t afford a new pair back then, but the internet provided me an avenue to popular shoe ownership.1
Doing the math, unfortunately, means I’ve had those shoes about 12 years now. I don’t know how much older than that they might be, but I’ve had custody for at least that long. I’ve done quite a lot in these shoes in that time. Perhaps a bit too much. When I was busy dragging branches to the curb after the storm a couple of weeks ago, I noticed a soggy sound coming from my soles. When I was finally done, I took the shoes off and found that part of the outsoles had completely disintegrated.
Well that sucks.
The logical conclusion is to chuck them out and buy a new pair. I’m an adult. I can afford new Sperrys. I can even get the fancy Gold Cup ones now. But I don’t want to do that. I want these shoes. So I asked around with some people who might actually know, and even they said that it’ll probably cost more to get them resoled than just to get a new pair. But it can be done, right?
Walk in my Sperrys and maybe you can see why they’re so special to me.
College
I was not a particularly preppy person before I went to Ole Miss. I was an emo kid in high school, and when I got smacked in the face by boat shoes and Norts and oversized Comfort Colors t-shirts, I really didn’t know how to pull it off. Sperrys were one of my first steps toward redefining my personal style to be more prep/trad and more in line with the aesthetic at school.
I wrote about my dog last week. I love him. He’s one of the most non-destructive animals in the world, but he wasn’t always that way. When he was just a little guy, he chewed up the leather on the heel of the left shoe, and that shoe has carried the scar this whole time. Murray will never be a puppy again and (hopefully) will never chew up another shoe of mine either.
Puppy Murray’s handiwork Riding a motorcycle during college was very convenient in some ways (parking spots actually existed after 7 AM, those parking spots were right next to my classes) and inconvenient in others (motorcycle gear is hot in the summer, carrying around a helmet and gloves and boots and a jacket is annoying). In an effort to reduce the amount of gear I had to carry around on campus, I compromised on ATGATT and wore my Sperrys on the bike, with the rationalization that they were leather, so that’s something, right? The left shoe bears the scuff marks of the gear shift lever.
Feeling like an adult
When we moved back to Dallas after college, these shoes came with me. I have a picture of myself at the dog park one day, watching Murray play with the only dog friend he’s ever had. I was wearing my cool adult boat shoes and cool jeans and a cool plaid shirt and a cool Fossil watch and I felt cool and adult.
These shoes have done a lot of two-wheeled transportation with me. I used to live very close to my first job out of college and was able to ride my extremely heavy mountain bike to work because it was only about three miles. I borrowed from the logic of the motorcycle trips and decided “eh, leather is good” and wore these shoes to the office, in an effort to balance safety and presentability.
Actually being an adult
I’ve gotten into prep/trad style more as I’ve gotten older. I’m copping the old money New England style more and more, and I try to also cop their approach to materialism as well. Namely, buy what you need once, take care of it until it’s falling apart, and then get it fixed until it’s a Shoe of Theseus (just to choose a random example). Part of this has involved learning how to take care of leather shoes properly. Because the Sperrys are my most beater leather shoes, I practiced leather cleaning and conditioning on them first. They don’t look too bad!
We went to Europe last month. I knew I was going to be walking a lot, and I didn’t know what exactly the weather was going to be like given we were going to be both in Greece and Germany. I figured boat shoes would provide a lot of flexibility and I wasn’t wrong. I wore those more than any other shoe I brought, and they were so great. I did notice that the sole was cracking during that trip, but there wasn’t much I could do, so I just kept walking.
That brings us to the storm cleanup when I noticed the insole was wet. There’s not much that can make you feel like a real person with responsibilities like cutting up a giant branch on the house that you own approximately 50% of so that you can try and get to a place with power and get back to doing your silly little email job. I was also able to deal with a complete shitstorm that I wasn’t expecting without being particularly upset, because this is just part of life sometimes, and I’m grown enough now to handle that.
So yeah, I’d like to get them resoled. I’ve become a whole person in these shoes. I’ve joined a sorority and adopted a dog and gotten married and bought a house with these shoes. I’ve gotten and left my first job out of college in these shoes, and visited Paris in these shoes. I’ve done just about everything except go out on a boat in these shoes.
How can I just start over with a new pair? You can’t just transfer all that experience and character into the next pair. It’s a whole fresh slate. And I’m not quite ready to let the person I was when I got those shoes go. So if you’re a cobbler, I’ve got a pair of boat shoes for you. I need them resoled.2
I also got my first pair of Chacos on eBay. They were all the rage back then, and frankly, they’re very comfortable and I don’t care how they look, okay? I have bought another pair since then and they also need to be resoled, but thankfully they have a service for that. I just need to actually stop wearing them long enough to send them in.
When I posted a request on Bluesky to see if anyone actually knew if it was possible to resole Sperrys, someone responded with this great website that lets you find cobblers that will repair your shoes. Shout out to ACME Sales Rep on bsky and Vibram.
So what I can gather is these shoes and their soles carry a big part of your soul in them...