I just wear what I normally do on an every day basis.. because if it goes past a first date they’re gonna see my in my normals anyhow.
Some crazy patterned leggings, my lace up boots, chucks, or weird printed Keds. Some solid tank or tee, with a shawl or some other opened cover with sleeves. (to cover my butt because leggings). That or some skinny jeans, same shoes listed before, and some weird patterned shirt with all my different length necklaces. I’m the queen of matching mismatched stuff together haha.
And nothing that shows off cleavage or short shorts. I like leaving plenty to the imagination. Also maybe a bit of powder and my signature winged eyeliner. I never wore much makeup beyond that.
Edited to add that if they specifically want to go to some super nice uppity restaurant, I’ll step up my game to a dress/skirt and shawl. I don’t own heels or flats so they’ll still get my keds or chucks, haha.