I prefer to wear jeans with nice blouses, shirts and shoes (Sperrrys and boots). Sometimes I will wear a sweatshirt or athletic shirt with sneakers. Do guys, especially preppy guys, prefer girls who wear dresses and heels or do they really not care?
I don’t think most guys necessarily care, but, at least at my school, if you wear a dress then you’re definitely going to get noticed because that’s not like a common thing. As long as they look presentable, that’s all that matters.
So, it seems to be very dependent on the guy
Why do you care if a guy cares what you wear? Wear what makes you happy!