This is a point that is often raised on here and its one that it easy to consider but hard to do.
It boils down to your age, the location and event that you are doing, be that shopping, having dinner or going to a show. Women (and men) will adjust their garb to suit the environment which they are in, so tend to compliment each other.
Think of doing work on your car as an example, then you would not (intentionally) wear an expensive silk dress with heels and white gloves to change the oil as it would most likely get ruined, however you would not wear greasy overalls and steel toe cap boots to a formal dinner … so you would plan the outfit for the event.
I go shopping, go for days out in the country and dress for the occasion in comfortable shoes and outfit – and then I go to Burlesque and glam up more with retro outfits and heels to match others at the event. However I wouldn’t wear what I wear for burlesque to go shopping during the day as the outfits are just too OTT and would stand out like a sore thumb in the high street!
Having a ‘ladies that lunch meeting’ is a middle of the road event were you would dress to match your peers as it would be more dressy than shopping but not as dressy as going to the theatre or a posh meal out at night.
Sadly I have met some girls who wear inappropriate outfits for the environment, with very high heels, short skirts and shiny material in tescos shopping at 10am… unless you are trying to make a very bold ‘this is me and I’m not afraid of being looked at’ , doing it for a ‘dare’ or part of ‘Rupauls drag race’, then this is not going to end well.
So think about your age, dress according the environment and location, and have a fun time out being yourself.
Again as aways these are jut my thoughts but having been out and about for over 40 yrs I think I have go the hang of its now ..but I’m never too old to learn !