The Winner is

Cardigan & Shorts- Thrifted, Blouse- Gift, Shoes- Circa Joan David, Bag- F21

Weirdest shorts of my life. But I think they fit perfectly in certain situations. Like when you go to a random sketchy neighborhood with your equally appropriately dressed friend. Then you both try to buy cheap socks because one overrated pair is just not enough. And hilarious comments are throw at you about your shorts and your friend's raccoon hat. But all ends well when you finally invest in a cheap pitcher for your mixed drinks.