I’ve enjoyed the videos made by stylist Alison Bornstein on this topic. She has an unusual system for culling. First step is to make a pile of everything you regularly wear, no matter whether you love it, are proud of it or embarrassed, all of it. Even your sweatpants etc that you wear every morning to walk the dog…all of it. Those all stay (although if you have time, you might see if any of it needs replacing or repair).

Next, a pile of all the things you NEVER wear. Then later you break this down: things you don’t wear because they don’t fit (discard) or you don’t like it anymore (discard). Then things you like but don’t know HOW to wear. Then you work on figuring that out.

Interesting, right? It seems very practical, instead of trying to figure out how you FEEL about each piece.

Welcome to the forum!
How about making a challenge to yourself to wear all of the pieces? If something feels not right on the day you wear it, it'll be a candidate to pass.
Alternately, you could track what you wear, and pass the things you don't reach for.

I have found one way of doing this and having some fun into the bargain- recruit a friend who's sense of style you trust (and who you feel comfortable enougth with that you are willing to allow her/him in your skivies). Set aside a period of time and go through your wardrobe, trying everything on. An objective observer can see more clearly than you sometimes can if something fits, flatters or is worn-out.
The process is more fun if you can arrange child care and a glass or two of wine is involved in the process......

JK, I just watched an Alison Bornstein video and now I want to try that!

I’m always so divided between keeping things I may want to wear again and tossing them. Thinking of them as “HOW?” may be more helpful.

I agree that things that you wear (even if you don't love them) are mostly worth keeping.

For example - my second pair of cycle shorts - I don't love them but on rare occasions when I cycle two days in a row I appreciate the spare pair.

Or the gardening shorts or the basic navy sweater that makes three pairs of pants work.