The Oldest Piece of Clothing You Still Wear

Today a friend who reads my blog and knows me in real life asked me if I was ever going to change the red banner at the top of my blog. I told her that I’d love to, as the photo is quite outdated, but I can’t find where my blog lets me change that section.

The photo there was taken nearly 9 years ago, which is super weird to think about. 9 years!

My friend asked if I still had the shirt I’m wearing in that image. I had to think about it for a second, but not only do I still have that blue dress shirt, but I still wear it on a regular basis. It’s even older than the photo–I got that shirt 12 years ago (2003).

My friend mentioned that she had a wear-around-the-house shirt that she got back in 1996–that’s 19 years ago!

I don’t shop for clothes often, and I keep my clothes for a long time, so I started wondering about the oldest piece of clothing I own that I still actively wear.

The last part is key, because I do have a few funny shirts I got from studying abroad in Japan during the summer of ’97. That’s 18 years. But I don’t actually wear those shirts.

I was about to settle for the aforementioned blue shirt when I realized there was one more candidate: A grey shirt I received the spring of my sophomore year at Wash U for participating in the residential college olympics.

It’s a great shirt. It fits perfectly, and the material is super soft from years and years of washing. It’s over 14 years old. I snapped a photo of it below (Walter is there for scale).

What about you? What is the oldest piece of clothing that you still wear on a regular basis? Why have you hung onto it after all these years?


11 thoughts on “The Oldest Piece of Clothing You Still Wear”

  1. I still wear some flannel pajama bottoms that I made in 7th or 8th grade to sleep. It’s getting to a pretty rough shape. I might turn them to sleeping shorts. Hmmmm… You know how people frame jerseys. I can frame them. The reason they are not in the trash because I made them and I don’t ever want to throw them away.

      • Oh, they are comfy. A little short since I already have to hem them once because they ripped at the bottom. They are the best and they just fit how I like it. Big, baggy loose pants that keeps me warm at night. 🙂

  2. I still wear a black t-shirt from my martial arts classes where I grew up. The phone number is mostly faded, and it’s stretched out a little bit since I first got it as probably a 13- or 14-year-old, so at least 20 years. I keep it because (1) I look like the wrong guy to mess with, (2) I feel like I really earned that t-shirt after 5 years of practice and (3) I want to try calling this number one day to see if it still goes to the dojo.

  3. I love my almost 20 year old shirt– it’s the softest pajama shirt now that it’s finally broken in. I have no idea why I originally kept it, but now that it’s lasted 19.5 years I figure I may as well keep it until it falls apart and is completely threadbare. 🙂

    Here’s a picture of it (with reference cat Hodor):

  4. I got a T-Shirt of the “Tour of the Universe” ride at the CN Tower in Toronto way back in 87 which my other half now wears occasionally!
    I have another T-Shirt from 96, which my first boss did for all the staff in an old overcrowded office – listing things not to do – like turn your back on your chair because someone will take it.
    For an item of clothing I still wear myself, I have a “Don’t Hassle the Hoff” T-Shirt from only 07 – though the printed image/words are pretty worn/broken now, still gets a chuckle from bored TSA agents.

  5. I have a World Cup ’94 t-shirt that’s still in remarkably good condition. Also, since it was “in” to wear clothing that now would be considered too large, the shirt that once swallowed my 13/14-year-old self now fits quite well.

    • 1994! Well done, sir. Yeah, because of my desire to wear oversized clothing in middle school, all shirts from that time would now fit me perfectly.


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