When girls take their glasses off and let down their hair...

Sounds like you could make it both ways but yeah I'd let down your hair and take the glasses off that'd really 'slap him in the face' as you said and he'll probably be blown away because he's never seen you like that. Trust me, it's worked on me before haha.

It sounds like you probably look great both ways. I think that if you let your hair down and wear contacts (if you have them) just the difference of appearance would catch attention, and probably add depth to your personality -- add a sort of sexy, mysterious, deep quality to you.

Skinny jeans and moderately tight t-shirt are hot btw

In general, I think both looks are great, and its hard to say which would look better without seeing pics. To answer your question: If I had to vote, Id vote for hair down, no glasses.