I have held onto pieces of clothing that are at least 5 years old, because they still fit me and I loved them 5 years ago, but I never wear them anymore because they no longer fit into my life.
I found a lot of little sequin dresses, studded jeans, rhinestone jeans, stuff that I loved when I first moved to LA and these things were trendy, but they aren't anymore, and even if they were, do I feel like the type of person who would wear rhinestone jeans?
I also don't want to come across as someone who follows every fashion trend (as I actually end to stick to the same kind of clothing vibe), but I do feel like this kind of thought process might be helpful to others trying to cull their closets.
You don't need to keep something that you loved 5 years, was super trendy 5 years ago, and you felt super hot in 5 years ago.