Pineapple is so awesome!!
It seems you are doing what I did last week - having a theme. You could pack these few pieces all up in a very small suitcase and be gone for a week's trip. I love that idea.
Overall I think:
1) You don't look that sick.
2) The trench is amazing. Fantastic color, fit, everything.
3) The H&M pin with the necklace (is it attached to the necklace?) is sweet.
4) The silver shoes in the Pineapple photo are wonderful and I want to steal them.
5) The polka dot wedges with the skirt don't bother me. I think it looks quite nice, actually. Gives you a little bit of a lift which is appropriate for skirts, and the polka dots are fun. The vamp is low and the wedge is working. I like! A lot!
6) My only concern is the cords - I am not sure but I think I might like this outfit better with jeans. However, it could be that you are all wet. There is something spring-like about the color of the cords, but the wrinkling bugs me. That could be that you got wet. Hmm, maybe you need white jeans instead?