Andrea H, you will be happy to know I read every word you wrote above! I have to agree that what we choose to keep or not may be a very emotional/sentimental choice as opposed to practical and based on some logical advice as imparted by someone. I love that you have kept your gunne sax dresses. Apparently, for whatever reason, also probably the spark of joy, I kept everything that was chocolate brown! I can even recall with clarity every chocolate brown item I decided to give away because it was too worn out to keep. I didn't keep anything olive or eggplant but I had a lot of those. I certainly didn't keep my collection of scrubs much to my children's disappointment at Halloween time, although at one point my dresser was filled with them. In fact I only wore hospital issued scrubs and a lab coat during the week for three years of my life. It made clothes shopping very easy! Shoes were simple too!
One thing I do regret purging are my grandmothers aprons. I'm not even sure I purged them or if they were in a box that went missing during a move. I strangely kept my first purse purchase, a coach bag bought when my DH and I were walking down a street in D.C. We had very little money and I wanted and purchased an expensive purse. It was maybe $200 which was a small fortune for us then. 30 years later, my DD is using the purse, so it might be One of the best purchases of our marriage!
I'm a believer in purchasing quality athletic gear if you use it frequently. Athleta wears like iron. It is expensive, but my Chaturanga leggings last six maybe seven years. I exercise 6 days a week, even with my injured foot. My gear sees heavy washing machine use. I get tired of it faster than it wears out. Seven years in the same exercise togs is a long time! (I only toss it if it rips, overly stained, too faded in color, or becomes see through, etc.).
It's impossible to predict what is going to be useful in advance. I think our intermittently seen friend, Marie Kondo is helpful when it comes to purging. If it still sparks joy, keep it. Even things that are sentimental can spark joy or lose that spark. I have gone back through things I was holding onto and realized they no longer had any pull over me. I tossed them.
It is a hassle to replace something you have once owned before. It's annoying. It's upsetting, etc. However, which is worse? Hoarding things just in case you might some day need it or having to replace a few items? My experience has been that it is often hard to sort through the many items I am trying to keep in order to find the one or two items in question. The more you decide to keep, the harder it is to find stuff.
I also live in a four season location. Even though I have a big closet, and some spare space, I try not to keep anything I am not using, or anything I don't think I want to wear again or that I am not intending to pass on to my DD because it has family significance. For example, I keep my great grandmothers cut crystal bowl that she recieved as a wedding gift, but I gave all the small pieces of crystal that sat in my cabinet unused forever to people who would enjoy it, and I don't keep the chipped crystal wine glasses I recieved for my wedding, I toss them. I will keep my real jewelry, but probably not my costume jewelry, etc. I definitely keep some clothing items, like the chocolate capsule, and certain favorite shoes, however, there is a limit to how much I keep. I also find myself reviewing the items I am keeping, and every once in a while I purge something. I try to keep that collection small.
I am in that sandwhich generation. My mother in law died last August, and my step father last March. They both had a lot of stuff. I don't want to leave too much for my kids or spouse to go through. It took my mom a few months to sort through my step fathers closets. He had four closets filled with clothes! Then there was his study, the basement, the garage, etc. My aunt had so much stuff she had a full storage unit plus her condo. It can be therapeutic to look at someone else's belongings, but it can be emotional, overwhelming and aggravating. Maybe this sounds morbid, but both of my children are autistic. I am always thinking ahead for them, always. If you are still reading, I'm impressed!