It depends. I have absolutely no idea what I was wearing the day that my friend committed suicide 6 years ago. I had worn those clothes many times before, and while most of the details from that day remain vivid, my clothes simply had too many associations attached to them already. I also got dressed that morning without the intention of it being a sad outfit.
However, there was a memorial service of sorts at the school that night, and I remember deciding to wear gray sweats and my brand new green and pink chuck taylors. I wanted to be comfortable and didn't care what I looked like (hence the sweats), and I wanted to be happier, and thought the shoes might bring some joy to an awful day.
The shoes have since become my "happy shoes". I choose to wear them for things that I know are going to be happy (and casual and somewhat goofy, what an absurd pairing of colors!) AND for times that I know are going to be sad or tough and I want some happiness (both from the absurdity of the shoes, and any happiness that has stuck with them from the happy events). I wore them the first time I hung out with my now boyfriend of 4 years!
I think you should do whatever will make you happy about the clothes. If you'll think about the bad news every time you see them, I would donate them or sell them and do something happy with the profit!
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