The analyses of conversations

Dad: You can't go to school looking like that.
Meg: I'm old enough to decide what to wear to school.
Dad: The only way to prove that to me is by wearing a long skirt or pants.
Meg: Yesterday I was wearing pants and you didn't like that either.
Dad: Those were too tight. Honey, the point is you need to wear something decent.
Meg: The point is you're not a guy my age.

I'd like to know if "looking like that" means "when you look like that."
And I'd like to know if "of" is implied before "my age."
Thank you in advance for your help.