Caution: long post

I'm struggling with downsizing my wardrobe. It sounds like lots of you are doing pre-season edits so I'm hoping for advice:

My present wardrobe is larger that I'm used to, and I'm having a real struggle editing it. I did a Fall 'try on' this weekend and was hoping the 'spark joy' question would help me cull. Unfortunately, when I applied it, the answer was: pretty much everything. Maybe I'm just easy to please, but everything felt good, had mates for an outfit, and made me happy. I have plenty of wardrobe space, so there's a home for it all, but I feel I have just *too much* stuff. I'm easily overwhelmed by choice. I desperately want to pare down.

Because I worry about looking dated, my typical MO is to get rid of items based on age (I'm a late adopter so if it's 3 years old I'm guessing out of style so I've been passing on). But I've had plenty of regrets with that -- not only is it expensive, I often miss the passed-on items.

To help me stay structured and corral things, I organise my closet by occasion, subset by item type and colour. My wardrobe is heavily skewed to my mostly office life. Still, many items only get worn once a season, sometimes because of maintenance issues (fragile, light coloured, dry clean only). I'm thinking I should perhaps dump these high-maintenance pieces even though I adore them. I've spent the summer trying to analyse whether I gravitate to a few items more often and, except for a couple of basics like white tees, I don't.

I'm currently purging based on age appropriateness, orphan colours, whether I'd buy an item again, and whether it elicits positive comments from others (since I'm often not a good judge for myself).

How do you choose what to pitch? What am I missing here?