Guys what type of girls do you usually approach? (out of the two)
cute chick in the sweat pants/yoga pants/maybe leggings with a graphic tee or just a shirt that says i'm not a slob but i'm not trying to dress up here.
a bun or pony hair do.
the beautiful chick whos well put together hairs in place and clothes are picked out. in other words the girl who put effort in it
i would say the setting would be casual. somewhere people frequent but its not an invitation only type place