I just did my clothes... Was actually a bit harrowing to get rid of some things I loved but were too small. Not surprised I'm fatter than that, but I am surprised I've spent so many years playing second fiddle to some hypothetical thin version of myself. All those clothes I might diet into took space in my wardrobe (and mind) from things I could have, genuinely, been enjoying right now.
This is where you thank the beautiful but obsolete stuff for the good times, get rid of them (and the functional but joyless stuff), and then you can make an unfettered decision about whether you actually need to buy something beautiful that also fits and flatters you now.
As for the functional stuff, I got this much more easily. I have had quite a collection of vests, which I wear all year round, layering them with other tops in winter. Some were a bit small, some had a bit too much stretch, some went baggy after 10 minutes wear, some were a bit cheap and cut off grain... Precisely four were smooth, and pure cotton, and fit nicely, and just the right length, and stop my tops clinging, and every time I rummaged in the bottom of the laundry basket and found one, I thought BINGO! I now have precisely four vests. They are as dull as ever, but they are the ones that bring me joy! If I find I need more than four, I will seek out the same again.