It is so rare for a woman to actually dress like a woman instead of a guy, that I would think she was more of a girlie girl just for wearing a dress. lol I would say that is just casual dress for a girlie girl. Although I don't think chucktalors and a dress would go with each other well.
okay. I prefer dresses over shorts anyday. And anyone who knows me knows that I am not a tomboy.. rather the opposite.
And honestly, converse and dresses are the cuuutest combo ever. Except, there's like.. basic requirements. the dress has to be short- higher then mid thigh, and the converse *should* maybe probably be lo tops. they just look cuter. more delicate. although I don't know if that's the look you're going for..
as for the hair down + no makeup, that's not very tomboyish. its just casual like SnackG said.