I'm 5'8"...don't care if a woman is taller in heels. Women are more self conscious about height than the average short guy is. If our eyes are closer to your boobs, we're happy.
Honestly though, barefoot with an extra long t-shirt is my favorite look. Maybe a tank top (no bra) and panties with cute socks. Heels are ok but overkill when going to see a lady.
