I also liked Audrey's sessions on re-mixing things you have not been wearing. Although she also had a decluttering post saying toss anything you have not worn in a year !
So this will be even more relevant to me going forward as I have moved on from a former major role as a practicing physician. But since I did not have to dress in any super corporate styles, I want to see if some of my items can be repurposed in new roles and in ever advancing age !

I have perhaps said this too many times, but my best "purges" are when I can see something just does not fit. I have to make some exceptions for items that might fit quite well over a 5# weight change, if they seem worth it--some pants fall here due to tailored fits and waistbands.
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What is easier to see even though it is painful that I did not see it or "listen" to my inner voice, are things that are too big in the bust (have still made jacket errors here and usually due to sales goggles), or too tight in the sleeves to be comfortable, too big or too small in the shoulders--things that are harder to tailor or require too much $$ for the result. Or sweaters that are too tight--this is an iteresting line between having some different fits--tailored vs fluid--compared to out of my comfort zone fits--or sweaters that are too fluid/oversized in the wrong way.

These edits plus a lot of re-mixing and some trial runs--even if just to the grocery store--are part of trying to figure out what I want to wear now.

To me, dressing my age has come to mean dressing the body I have today and (sigh) my fussy feet. I (mostly) avoid orthopedic looking footwear as well as prints that I regard as looking "old lady". But, at age 67 I dress to please myself. We won't have in-person church services for at least the next year, so I no longer have to meet the (heightened) expectations from church folk who apparently check out what I'm wearing from week to week.