re: What the oldest item of clothing you can still wear?

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The oldest thing I own (but don't wear) is a leather jacket with wool trim from the 1970's. It looks awesome, but I'd have to lose 20 pounds before I could ever squeeze into that thing. It's only a 36 and I usually wear a 40S.

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So you’re disappointed you can’t fit into a child’s jacket

I have a shirt from basketball camp I went to in the 7th grade. I was a fat kid

A Pair of Retro 1 J's and Kobe all-star edition shoes. Both about 12 years old now

I have a couple Ralph Lauren polos that were acquired in the mid 90’s that are still in good shape.

Black Tee with the CAT logo on the front. It’s at least 25 years old. Made a guy give it to me that went double or nothing in darts. He didn’t have a penny on him.

I took a pair of 32 jeans from a dudes house whose wife I was bonking. I can't wear them, but I be he can.

APFT shirts, BDU field jacket issued in 1998. I have stuff that's older I could probably still wear up in the attic. I have a late 1800's era officer's hat that fits.

LL Bean warm up jacket that my mom bought me for Christmas. That thing is 26 years old, Made in USA and has held up remarkably well.
I seriously doubt anything from there now would last that long.

I have an old UF football tshirt from when I was in middle school