I had a high school reunion in August and because my hometown was pretty much surrounded by forest fires, roads closing, including the whole town shutting down, I decided not to go, as did almost the whole class, only a few showed.
For that occasion, I had chosen one dressy outfit and one casual, head to toe, intentional dressing. Twas so much fun putting it all together. And it motivated me. What I learned is that I need more occasions to dress up for and I do live in a casual environ.
I am retired now. I always dressed well at work, maybe a step up from the norm. Never wore jeans except on non-teaching days when I was in my office grading papers (college teacher).
I'm all for "creating" occasions to dress up for. That act itself instills self-care and keeps us upright!
Angie, my son now lives in Seattle. That is, indeed, a casual city. Even in very nice restaurants, I saw casual wear 70% of the time. When my son suggested going out to eat, I always dressed up a bit. His reaction, "mom, this is Seattle. you're fine." But he seemed pleased when I did. My folks lived in Kingston for years, across the water from you, and they always dressed casually.
When in Rome . . . on a vacation in Crete, however, a lot of people dressed up at night. I loved it seeing people of all ages, wandering the streets, in dresses and skirts, heels as well, even though it was summer and tourist haven.