For simplicity, let’s define “all dressed up” as putting more thought and effort into your attire than for your normal activities, whatever they may be.
Even before I retired, I led a very casual life. Fortunately, the dress code at work permitted me to wear non-blue jean pants and most tops as long as they weren’t revealing or classified as graphic T’s. So dressing up might involve my one dress, or one of a couple of nicer pant suits, and nice loafers or flats instead of sneaks or oxfords - I don’t own any high heels.
Funerals and weddings definitely require nicer attire. On the rare occasions at work when I got an award and I knew there would be photos, I’d step it up a notch from my usual. And once a year when my mom invites us out for a really nice dinner in a fancy-pants restaurant, I’ll pass on the jeans.
I suppose if I got an invite to the White House or something really special, like an appearance on The Daily Show, I might even buy something new. But that’s about it. We don’t go to the opera or to balls or to red-carpet premieres and most of our family events are very laid-back. It’s pretty funny to see me in photos all gussied up as a kid, in a hat and little white gloves and shiny new shoes and purse - I don’t miss the 50s and 60s.