First off I want to say I love your style! Second, I completely understand the power of that moment. When I met my now-husband the first time, he later said that one of the first things he noticed was the button pins on my hoodie
I do think it's important that whatever you wear is something that feels natural to you, because that is what you'll feel the most confident in. If you are too conservative, you might find yourself wondering later if his response, whether yes or no, was because of that. On the other hand, you don't want to feel like you're trying to hard and be self conscious.
I think this outfit is perfect. The tights are feminine and cute, the vest is sassy. I love combat boots with anything!!
Have you thought about accessories yet, hair and makeup?
Can't wait to see the outfit, I hope you post it later