That would have to be the Aloha Shirt I’m currently wearing. I don’t know how old it is, but it was a hand me down gift from my Mother. Now the oldest piece of clothing I own just so happens to be an Aloha shirt as well. My Mother actually made it for my Father when they were living in Hawaii back in the 60’s, and now it belongs to me. I don’t have (or want) a lot of stuff that belonged to my Dad, but that shirt is one of my prized possessions.
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It has to be the black one and I think it has metal Kamahamaha buttons. You Dad wore it a lot and I am glad you re still wearing it too.
I’d have to say (embarrassingly) my undergarments. I don’t know about other gals, but I wear them past a reasonable point. You know how there’s a saying about having nice undergarments on when you travel, “just in case”? My comfort would not coincide with the spirit of that statement. 😁