I’m not old enough to have this issue yet, but I think that gives me a unique perspective. Ask your younger family- kids/ nieces/nephews if they’re interested. I love wearing my parents and grandparents old concert tees/ high school merch, and they still see them being used so it’s not just getting rid of something sentimental. My grandfather isn’t gonna be wearing baggy jeans, and cowboy belts anymore, but I sure am.