Most Helpful Guy
Cute but not over the top.
I went on dates with women who were clearly virgins but over-dressed and ended up looking like cheap hookers. The "inexperience" was sort of blatant and sort of a turn off.
There is absolutely nothing wrong with going for coffee on a first date wearing leggings and a cute sweater.
Most Helpful Girl
I would say something that reflects your style. I assume you’re in high school, like I, and will not be going to some type of bar or extremely fancy restaurant. So definitely dress casual, semi-casual. I’m a very feminine girl, so I’d likely wear some cropped white jeans, a gooey shirt and low rise converse. Again, let it reflect your style though!