How do I subtly manipulate someone into changing an aspect

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>>16666627
Holding them hostage at gunpoint tends to work out pretty well.

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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.

>>16666627
You tell him abruptly.

>>16666627
You don't. There might be reasons hs/her appearance is how it is. Instead, try to understand why...