I find your thoughtful reviews insightful and moving. I'll try to keep mine a reasonable length. TL; DR, I embraced tomboy looks this year; hoodies, sneaks, denim, but kept wearing my "nice" items whenever I felt like it.
I retired (as planned) in July 2021. The previous two years I had tried not to buy anything that I could only wear to work - no blazers, no pumps, etc. I started weeding my closet with hopes of making big donations to Dress for Success. I had a lot of good quality work wear and I'm a 12-14-16, which is very useful for them. But alas, they still are not taking physical donations, so I put them on a monthly $$ donation plan instead. All those pretty blazers and skirts and dresses. *sigh*
I gave away my heavier or fancier necklaces to work friends (this was fun!). I never wear them at home. Jewelry in retirement means earrings and watches and rings.
I beefed up my exercise wear with Title Nine, Athleta, lap suits, and proper shoes for hot and cold hiking. Good gear is expensive!
I wore casual dresses and denim shorts all summer, no change there.
In cooler weather, I wear anything I like that is comfortable,
"dressy" or not. Why not wear a fake fur to the library?! they know me there.
A couple of fails; pants that were really too tight in the waist. They looked great, but were annoying after an hour or two. They're still in my closet, but just for going out, not all day wear.
Another fail; having a million scarves. I don't wear these around the house (like those necklaces) and will probably have to weed some more soon. At least I didn't buy more in the last two years.
The successes; my Ecco high tops in black and in white. The perfect fall shoe. Lighter and more comfortable than boots, plus they make me feel as bouncy as Tigger.
Fun denim! I bought overalls, wide-legs, and destroyed jeans this year, and wear them often. Wide-leg pants in general, really, I found myself suddenly annoyed with skinny pants.
Hoodies! I bought three this year. So soft, comfortable, and they keep my neck warm. Perfect after swimming.