What most naturally follows?

How to dress to meet a boy for the first time
Research where you will be going to meet him.
When you are trying to decide what to where it is helpful to know when and where you will be going. You dress differently for church than you do for school than you do for the club.
In the same way, it is good to know what is considered acceptable for the the place you will meet. Your outfit will be influenced by your surroundings.