How I felt: I honestly thought this was going to be the hardest outfit to wear, but now I get why Kim Kardashian gave her biker shorts a formal twist by styling them with a tuxedo jacket. My blazer and kitten heels made the biker shorts feel more polished, and I sort of felt like a modern-day princess. I'm not saying I would wear this look every day, but if I'm feeling adventurous, I would wear it out for a dinner in New York.