I get rid of items if they don’t feel like me anymore or if they look tired or something is wrong with them-condition, fit, etc.
I keep smaller clothes when I gain weight, but I get rid of larger pants. I often can have skirts and tops taken in. I try to discourage weight gain by not having larger clothing but I and am happy to see “old friends” when I lose weight.
I am hard to fit and quite picky, so having clothes to wear without shopping is a plus, especially during Covid. Also, often the quality of the older items is often superior.
My sentimental items that I don’t expect wear are in one spot. Holding zone items are separated into weight loss needed, alterations needed, and thinking about.
I often pull items out of thinking about. I even had a dress that didn’t sell at consignment turn out to be perfect for a wedding guest outfit-after spending a lot of time shopping for the right outfit.
I also don’t purge items if I still like them as I want to use up my clothes instead of shopping for new.
Have you played in your closet with the items you are considering purging. I often find new combinations I really like.
I would keep a few of each type of item or at least think through all the occasions that could happen in the next few years. A wedding guest outfit, a funeral outfit, etc,
Good luck!