How To Hang On To The Same Outfit Well Beyond Its Expiration Date

You can pry the skate shoes off my cold dead feet

This pile represents roughly a third of my skate shoe collection and if I'm being fully honest with you, dear reader, these are the ones in "good" condition. It gets worse. Much worse.

I’ve always envied cartoon characters, although not for any of the obvious reasons but for a very simple, stylistic one. They never have to think about what they’re going to wear. Remember when Inspector Gadget would open his closet to reveal 45 identical trenchcoats waiting for him? That’s my ideal.

It isn’t that I don’t like fashion or trendy clothing; it’s that once I find something I like I don’t ever want to have to think about it again. I’ve been wearing LL Bean’s tan corduroy pants for going on two decades now. Why? Because I like them, they’re neutral enough to work for most occasions, and I know they will fit. It takes me 30 seconds to find them, purchase them, and go about my day. 

Over the years I established a uniform and it’s remained pretty constant. Ballcap, tee shirt (usually of a band or defunct minor league baseball team), hoodie (when applicable), the aforementioned cords, black ankle-length socks, and sneakers. All of this has remained pretty constant since I was 12, with the exception of the sneakers.

It took me forever to find a pair of sneakers that did the three following things, all of which I consider dealbreakers. 

1) The ability to put them on in under 10 seconds

2) Some level of resistance to water

3) They can’t make me look like an enormous dork

In my experience, there is but one style capable of meeting all three requirements — the chunky skate shoe. When I say “skate shoe” most people will think of Vans slip-ons or Chucks, and while it’s true that folks skate in these, that’s not what I mean. I’m talking about the heavily padded, clunky skate shoes of the 1990s. 

For me, it all started in 1991 when  Airwalk released The One. I got a pair during Back to School shopping and learned the type of sneaker I wanted to wear for the rest of my life. They even had the added advantage of being cheap enough that my parents would buy them for me (around $20). I wore them every single day until the soles fell off and other than when I laced them up and first put them on while sitting on one of those weird little stools with the mirrors on the sides in the middle of a Payless Shoe Source, I never considered those laces again. I just slipped in ‘em and kicked ‘em off when I got home. I became spoiled.

Throughout the ‘90s and early 2000s, every skate shoe company made some variation of what I always call “the chunky skate shoe.” Etnies had dozens of slightly different variations on this theme. DC famously took things to the extreme with the Court Graffik and its aggressively puffy tongue. Vans mostly stuck to the classic Old Skools and slip-ons, but their Geoff Rowley 66/99s were a dream. When Airwalk came out with The Scorch, which looked like it was designed to be Guy Fieri’s signature shoe, I picked up multiple pairs because I too have impeccable style.

The Geoff Rowley 66/99 was the perfect shoe. I have yet to summon the strength required to throw these out and I doubt I ever will.

What I regret is that I didn’t pick up doubles and triples of every skate shoe back then, because by 2010 fashion had moved on. Nike started making skate shoes and everybody else seemed to follow their lead. Shoes got sleeker and started to have a bunch of nonsense on them. And most egregiously, you couldn’t slip them on and off with ease. I became a man without a country.

I was unable to handle this development. I even went through all five stages of grief:

1. Denial  — They just don’t have the styles I want at this store, I can find them elsewhere.

2. Anger — How dare they stop making my favorite shoe! I hope all these companies go out of business.

3. Bargaining — If I find one specific style, stick to it, and buy enough pairs, they won’t possibly discontinue it. Right? 

4. Depression — My feet will never be happy again. Thus, I too will never again feel joy. 

5. Acceptance — Sitting down to tie a pair of Chucks isn’t too terrible, I’ll make do. 

While I was wallowing in my self-dug pit of despair, a glorious development took place — the kids started getting into the ‘90s. The jeans started getting bigger. The shirts started getting bigger. I took notice and a little sprout of hope started growing; maybe the shoes would get bigger too. And they did! A bunch of the aforementioned skate companies started reviving older silhouettes and I fell in love with the Etnies Windrow. 

The Etnies Windrow is what brought me back. This is the third pair of them I've owned and if you look really closely you'll see the piece of duct tape that protects my heel from getting stabbed by the plastic breaking through.

The second I saw the Windrow I knew we were back. It was the perfect balance of chunky skate shoe without being over the top. It was a throwback that people would comment on (“Holy shit, I haven’t seen Etnies in years…”), but it also blended into today’s fashion well enough that an over-the-hill punk like me could pull it off. I bought a pair. Then another. Then the three pairs that sit unopened in my closet. I have become a prepper and when the next shoemageddon comes, I’ll be ready. 

When you open my closet you’ll find countless dark shirts with band logos, a column of tan corduroy pants, and a row of green and white Etnies. OK, that’s a lie, my closet looks like a tornado hit it. But those are the contents. I’ve managed to acquire an Inspector Gadget-esque wardrobe… and I’m working on the organizational skills.