I think I decided on my outfit. Maybe it is "too sexy" though ... short flutter sleeve pink, purple and black floral print fitted chiffon top with a tie at the neck and deep v collar, black lace bra underneath, black below the knee rusched pencil skirt, black wide belt at the waist, purple-pink croc pointy toe pumps.
It's not a first date. I haven't seen this guy in awhile and am excited to see him again. I'm not really a casual dresser so this is casual-ish for me. Somehow the outfit looks more relaxed (and not busy) sitting down (it doesn't look as busy as it may sound either), and it really gives me an hourglass shape. Hair will be down or partially down. I like the idea of berry-colored lips ... will try that out, maybe with very neutral eye makeup and a hint of blush.
I want to look pretty, feminine, sweet and uncomplicated, just like the girls he likes.