I think the flip flops are fine as long as: 1) your pants have a slim or skinny fit (NO BOOT CUT WITH FLIP FLOPS), and 2) you roll up your jeans a little bit, and 3) your feet are in decent shape.
I would say dress in what you feel you look good in, not what you want to project. I have a unusual sense of style and I always feel most confident if I dress in a way that makes me feel good. Your personality and charm will win the game so get a head start feeling as confident as you can be.
The best advice in this whole thread. Just dress however you want as long as you feel comfortable you will be fine.
yes i would want my guy anyway to dress how they want. don't try and dress to impress or whatever i don't get down like that. like i mean, don't stifle yourself. oh man. i'm imaginin if my date guy or whatever straight up bitched at me in any way for wearin flip-flops or whatever. lol i'd be like bye bitch and sashay away.
I mean, it's whatever floats your boat. If I were you, I would ditch the flip flops and go for some suede shoes or something. Well, that depends on where you plan on going to. I say do what you want. I like everything else though .