BoyFriend shorts are tricky to wear, but I also think boyfriend jeans are also tricky to wear. They are just so baggy compared to my straight leg or skinny pants that I know and love. The shorts I have on are by William Rast. I love his jeans by the way... But when I bought these shorts I went with my normal size since I had not purchased boyfriend pants before. I quickly learned to always go down a size. But with these shorts I just have to deal since they were a pretty penny. I paired these shorts with a hot pink belt from jcrew, button down top from the LOFT, Fossil watch, (fabulous) Kate Spade purse, and Rainbow leather sandals. I wore this look to go babysit. It was comfy but still cute!