Hee hee - I love it! I wear Punky Brewster socks all the time! I'd do the orange, as long as I wasn't going somewhere like work or someplace important. But I always did that at college. (I don't know where you're at, home, college, work, etc.)
Side story about college and matching/looking "made up:"
In my college experience, you could always tell when high schoolers were visiting the campus. They'd be the ones wearing a ton of makeup, trying to impress the college guys. The university girls would be wearing sweat pants and a T-shirt, and casually chatting with the guys. It was so funny to watch the high school girls checking their compact mirrors and all. Little did they understand about rolling out of bed, and changing into something to get to an 8 am class.