My all time favorite outfit on a man is plain black tee, blue jeans, clean simple sneakers/black boots and a leather jacket.
What's yours preference?
I often hear guys saying they want their girl to dress modest and/or comfortable especially for a casual date, does that mean you should be 100% true to yourself? Are sneakers allowed? Combined with a dress if it's nice outside? Or is it okay to wear something simple but cute like a nice top and jeans that fit you well + them sneakers?
I like to make it more special by other things like curling my hair and putting on some flirty lipstick.