I have a veeery defined taste on clothes, sometimes to an extreme. I take too seriously my own philosophy about how I prefer my clothes to look timeless, simple, comfortable, elegant yet fresh, maybe a little contrast here or unmatching earrings there to keep it from being too perfect (=old), and how I like my clothes to let my personality take the spotlight. I do not accept for myself  an exposed underwear, an overly patterned piece, something too fashionable that may go out of style quickly, blah, blah, blah...
I would chose the outfit of the second girl everytime because it seems more like my myself (and don't get me wrong, I love it). But it was the first girl who made me think: She is wearing this puffy, orange sweater with a giant zebra (which probably you have noticed). This part-Sonia-Rykiel-part-Janis-Joplin vision made my day. You don't know how grateful I am that not everyone shares my vision on clothing, that they are a few people out there willing to entertain us, to make a statement. 
She gets a trophy because her personality shines through the sweater. She wears the sweater and not the other way around.