Let me explain this outfit. I'm going on a date, so I want to feel 'nice', but not overdone. I love the comfort of a pencil dress; I enjoy that my boobs are safely away, nothing can fall down or out (!), but it is essentially tight and 'feminine'.
I don't like to wear heels in the early stages of dating, so I mismatch a smarter outfit with crazily casual shoes (and crazy socks).
I don't wear lipstick at start of dating either, I feel men find it intimating, and its something else to worry about - is it still on evenly, has it smudged etc etc.
My hair is swept and pinned to the side, with some sweet pink flowers at the back, and one row of extensions just to give a bit more length and volume.