18 Days to 40: What’s the oldest item of clothing you still wear?

Tim Hammill
40 Days to 40
Published in
4 min readOct 3, 2020

I’m a T-shirt guy. If the climate and office culture allowed it, I’d wear a T-shirt every single day. I spend way too much time searching through Homage, my favorite T-shirt brand’s website. I even make and sell my own T-shirts on Threadless.

So it’s no surprise that my answer to the question in the headline above is a T-shirt. Pictured above is my 15-year-old Run-D.M.C. T-shirt. The shirt is one year away from being old enough to drive in some states. It’s been with me for 37 percent of my life. Of course, I still own and wear this shirt that I bought during the second Bush Administration. Look at how glorious that thing is! Yup, that is indeed felt.

I remember where I first met this beauty. It was at a shop in Los Angeles on Melrose Avenue called Workmens on a Friday evening. How do I remember this? Because when I was an account executive at public relations firm located in the Pacific Design Center, I’d treat myself to a new T-shirt right after work every pay day, and Workmens was my spot.

I picked up some incredible T-shirts at this shop, including shirts that prominently displayed my love for: A Tribe Called Quest, DJ Premiere, and DefJam Records. But unfortunately none of those shirts survived. To be fair, it’s a lot to ask cotton or a cotton-poly blend to last that long.

Fortunately, I’m still Raising Hell with my Run-D.M.C. tee. And good thing I never lost it because I had a tough time when I just tried to find it on the internet, where they say you can find anything, including this video of Vanilla Ice destroying a VHS copy of “Ice Ice Baby” while Jon Stewart, Janeane Garofalo, Denis Leary and Chris Kattan do their best to avoid catching shrapnel from the vanilla meltdown. The only thing I found was this Pintrest post with a broken eBay link.

The highlight of me walking this way with my Run-D.M.C. shirt was the time I ran into Darryl McDaniels, the D.M.C. of Run-D.M.C., in the aforementioned Pacific Design Center while wearing this shirt. The building was home to many entertainment industry offices, so running into a celebrity like DMC was not unusual. It was unusual, however, to run into someone famous with a picture of their face on my torso. Unfortunately, I don’t think DMC spotted it because I got no reaction from him whatsoever.

He may not have reacted, but over the years my shirt has earned me many compliments. And that’s kind of the best part of being a T-shirt guy, those times when someone stops making eye contact and looks directly at your chest and says, “nice shirt.” That’s part of the reason why I still wear my Run-D.M.C. shirt.

The other part… because it still fits.

On and off (but mostly on) for the past 15 years and then some, I’ve been wearing the same size t-shirt — XXL. There was one brief stint when I got down to an XL, that would be 2014 when I dropped 60 pounds in four months thanks to my marathon training.

But outside of that, it’s pretty much been nearly two decades of double x’s, or dos equis, if you’re the most interesting man in the world.

And that transitions nicely into my next post where I will weigh in on my weight, which I’ve been considering writing about multiple times in this blog but I keep putting it off because it’s kind of a difficult subject, or in the words of Run-D.M.C., it’s tricky, tricky, tricky.

While you eagerly await my next post, feel free to comment with the oldest item of clothing you still wear.

Tim Hammill is a communications professional in the nonprofit sector. He’s turning 40 on October 20, 2020. He’s writing about the final stretch to this milestone age in 40 Days to 40, a collection of stories, thoughts, reflections and whatever else comes to mind each day. In addition to writing a blog, Tim has also decided to donate his birthday to This Is My Brave, an organization he very recently learned about that brings stories of mental illness and addiction out of the shadows and into the spotlight. If you’d like to support Tim’s birthday fundraiser, go here.

Additionally, there are three other organizations that are close to Tim’s heart: Save the Children, Stand Up To Cancer and the Bridgeport YMCA. Click on each to learn more and to support their work.

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