In general I only very rarely make any comment on what anyone else is wearing. I find ALL comments on someone’s appearance to be judgy.
And I really dislike judgy, but sometimes if one of my kids has a new outfit and I can see that they are proud of it I will make a compliment, like, “I like your outfit”. Then they will usually tell me from which thrift stores they bought the various pieces. Or if my friend that likes to dress up puts forth a little extra effort for a night out I might say “you look nice” because I can see she took some extra time, but honestly she always looks nice because she IS nice and kind.
So that is where I am coming from with “you do you” a phrase which I really like actually because my weird kids (who embrace the term weird) use it. Be yourself! Don’t let fear of others’ judgment of you hold you back from how you want to dress or express yourself. If you like to dress very conservatively and modestly then do that. If you like to dress like Bettie Page then do that. If you like to dress like Lady Gaga or Elton John or Kim Kardashian then do that.
Honestly, unless the people you gather with are especially catty, I would suspect that most people who say “You’re so dressed up” are actually thinking to themselves, “Should I have dressed up? Did I miss a memo? Have I made a social faux pas?” What they say is often more about them feeling insecure than it is about you.
So in answer to the original question, my 21 year old will be wearing many facial piercings (ears, nose, bridge, cheek), tattoos, and probably all black — black jeans, and a black or grey sweater would be my guess, but a silly holiday sweater is not out of the realm of possibility and Doc Martens or maybe black Toms. My 18 yr old will probably be wearing a dress or skirt either mid-thigh length with fishnets, or possibly ankle length, also probably black, possibly brown or grey. Probably a crop top and a sweater and tattoos and Doc Martens. My husband will probably be wearing jeans and running shoes, and either a button down plaid shirt (not flannel, though) or an athletic synthetic material shirt with a nice black Saucony jacket. I will be wearing some Lucky jeans I got at the thrift store several years ago brand new. They only have a couple of very tiny pulls from cat claws. I will probably be wearing a long sleeve green t-shirt with subtle stripes across it I got from Target. Maybe I’ll wear a necklace, but sometimes they give me a neck-ache. I’ll probably wear some modest hoop earrings. I’ll probably wear my Skechers on my feet since I have a twinge of plantar fasciitis otherwise I would usually wear my black boots that look kinda like motorcycle boots, but not really. That’s us dressed up a little bit.
Oh, their cousins will likely wear t-shirts and jeans. I think one of the girls wore a dress last time we got together. Grandma will wear comfortable slacks, maybe a nice cream colored turtleneck with a pretty necklace and a cardigan.