Normal warm day: Cargo shorts, T-shirt (Aeropostale, Nike, whatever really), Nike or And 1 socks, Nikes or Jordans for the shoes. Doesn't matter what underwear really. Usually just regular briefs (this goes for all days.)
Normal cold day: Dark jeans, T-Shirt (same as above), Long Nike Socks, Nikes or Jordans shoes.
Dates really vary tbh. Depending on who it is or how interested also. Most of the time just regular everyday clothes unless I know a certain girl's taste is more towards the casual side. Recently though, I've been dressing nice. Button up shirt, white underneath T-Shirt, cargo shorts or jeans don't matter, shoes are the same and socks are the same.
Like I said, dates really vary.
Also, I've been thinking about shopping for a spice up in my wardrobe. So if that happens I'll probably break away from the cargo shorts and such.