I live and die by my spreadsheet, but it seems like I run mine a little differently - since most of my shopping is via thrift stores and similar, I don't really track my costs as much as others.
I track my outfits by date, as shown in the pic, which allows me to pull the data out into another sheet and sort by item or activity - if I want to see how many times I've worn "hot pink maxi," for example, I can sort by that column, and see all the times I've done, and with what - and if I wore it for travel or work, or how often it's been casual outings, and so on. In another page, I keep a log of my purchases, so if I really want to look into those numbers, I can compare them against the wears I find in the above; that part is pretty simple math
1) Sample of data tracked
2) Tabs that I use to collate data across the various sheets
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