Well, I just realized this post is not new (thanks to a spam post which I removed), but I’m glad it got bumped back up because I missed it the first time around and I enjoyed reading your line of thinking, Celia!
It’s so odd the way situations can imbue a wardrobe item. I have a hard time wearing the coat I wore a year ago when I face-planted riding a Lime scooter (thankfully other than a knot and nasty scrape on my chin and a scraped up hand, I was unhurt). Every time I pull out that coat, the association is there. I haven’t given up on it yet (especially since I’ve not had much occasion to wear it this year anyway), but I sometimes give it the side-eye in my closet.
Conversely, I wore this patterned skirt for the celebration of life party after one of my dearest friends passed away this year. Her family asked us all to dress in bright happy colors, as she loved to do. I wore this skirt with a red sweater. Normally I would expect that associating an item with a memorial would make me sad, but because of the tone of the event, as it was set by her loved ones, the association with that skirt makes me smile and think of her warmth and her smile.
Memories and wardrobe items can be powerful!