I don't think there's a problem with it. I would suggest wearing shorts (like spandex or whatever) under the dress just in case you change your mind and do want to go on a ride so you don't accidentally flash anyone. Otherwise, that's totally fine. =) And, like sikoo31 said, basically wear what you want, and forget the haters. =)
Sounds good. Maybe wear some white or red or black chucks to look more casial and not overdressed...but then again, you can never be too overdressed. Its better being overdressed then underdressed...just do whatever you want :D
But I think a jeansjacked a black dress, black seethrough thights and chucks would look great!