I know what you mean, San! I'm not retired - just unemployed, unfortunately, but what I've started doing is dressing nicer every day, even if I'm just going to the grocery store.
I have quite a few nice jackets from Ann Taylor from my working days, and I love wearing them with jeans. I've just started wearing woven shirts again, so for instance, yesterday I wore a French blue button-down type of shirt, a solid blue jacket (from AT), and jeans. I just ran around and did errands and grocery shopping, and I did feel a tiny bit overdressed, but I didn't care. I felt good. I felt like a person with a life, instead of an unemployed bum!
Of course, when I got home I took off the jacket and put on a sweater, but it still felt good to make that effort during the day. I don't want to keep saving my "good" clothes. I want all of my clothes to be things I wear all the time. We'll see how that goes!