My family has a tendency to hoard things. I am the best at getting rid of things. I think Mo nailed it: does it bring you joy or bring you stress? If you have anxiety about it, then it is a good reason to evaluate why you are collecting and keeping the things you are. My mom has tons of old clothes that are unlikely to be back in style that she is hoarding for future wear. She also has a very small house. I'm working with her to help her get rid of some of those things. So you can imagine, this idea has been on my mind a lot the past few years.
I went through a major closet purge this last spring. I lost weight and was ready to get rid of things that weren't fitting me anymore and things that I had saved (for when I lost that 5, 10, 15 etc. lbs.). I was merciless. It was painful. And at the end, I felt fantastically free. What I'm learning from getting rid of things (and I'm still learning it, believe me) is that things I keep after my love for them fades put a burden on me. I feel the obligation to wear them. While that is helpful sometimes (the moment you remember you have just the right topper in your closet already), it is not most times (the day after day that you drag a joyless item out and wear it instead of the newer thing that you love). I also found that it kept me from really getting the wear that I wanted out of new things that I loved. The old things were stealing my wearing opportunities from my new things.
So the only things that I think it is worthwhile to keep are those that make you happy. When they cease making you happy, you should let them find a better home. If you have a ton of boots and they all make you happy and you wear them (or are willing to save them for 20 years until they become personal vintage), then you are good, even if you have a collection.
