Positive reinforcement. Let's assume you like when your girlfriend wears dresses, but she only does so for special occasions. >Wow Anon, you look gorgeous in that. I think dresses are so feminine and elegant/sexy/hot [insert adjective your girlfriend would like to identify with most], maybe we should find excuses to dress up more often If she's not worn them in a while and you want to see her in them: >Hey Anon, remember that little purple dress you always used to wear? I miss seeing you in that, it was so cute If she's never worn them get in a setting where the topic can naturally come up in conversation (for instance a clothes store) >Wow, this looks amazing, I bet you'd look great in it and ask her to try it on then call her stunning and visibly check her out.
Obviously if it's not someone you're sexually/romantically involved with you're going to have to adapt this quite a bit to a level appropriate to your familiarity but the same general advice applies.
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