My immediate reaction would be admittedly hypocritical. See I’m of the opinion that, unless the alternative is obscene, dressing up for any kind of occasion is an irrational social construct. This includes wearing black to a funeral or not wearing jeans for a job interview. A “well dressed” person tells you nothing about them other than the fact that they are aware of these social norms.
My reaction would be hypocritical though because I automatically make the conservative assumption that people truly, genuinely care about what other people wear. Which means if I see you with pajama pants in public, my immediate reaction is that you’re one of “them” and that you’re too lazy to put on anything “respectable”.
See I have this theory that 90% of people in this world don’t truly, genuinely care about meaningless aspects of our society like dress code, elbows on the table, and other equally senseless constructs, but we conform out of fear of judgment or reprisal by people we think care, but really don’t.
Then I realize that you might be like me and you just don’t give a tinker’s damn about what you wear as long as it isn’t obscene.
Then there’s the possibility that you live right next to the grocery store and you just wanted some milk. I live right across the street from a grocery store, and whenever I need something I just go in what I’m wearing currently. But I will always put on shorts or pants but only because I don’t want to get my house pants dirty.