You're going to have a lot of fun!
"From what I can tell, best way would probably be to start off with revealing clothes/risky clothes. I thought of something like shirts that fall low or skirts/dresses or clothing that is semi-transparent? "
Robert, you have the right idea here; there is no need for an overly elaborate plan or special event. Take your girl out to a restaurant or bar, have her wear a low cut blouse, a blouse with an extra button or tow undone, or a semi-sheer top (with something over it to be opened later). Nothing underneath. Look for a place with lots of male staff, then during dinner or drinks have her discreetly adjust her blouse to provide a nice view to your server or bartender and enjoy your evening! The key is for her first exposures is to look relaxed, accidental. That can be fun to practice at home so she'll know how much is showing.
If she wears something transparent under a jacket or sweater it's easy for her to open it a little or a lot depending on your surroundings and audience.
Good luck and take photos before, during and after. If you get an interested server and she is feeling bold, have him take your photo at the end of the evening. And of course, let us see!
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