7. Jamie-Lynn Sigler looking awkwardly unfashionable in L.A. with a bulky scarf over a simple black dress paired with some sexy sandals that just don’t match. If the scarf were with a sweater, the dress with different shoes, or the sandals with skinny jeans, her look would work. Unfortunately, though, it is just all wrong. 9. Jay Mohr, with his pink leashed pup in New York, pulls the quick-fix prep style trick of throwing a sport coat over his football watchin’ attire- and ya know what? It works for him. Jeans, t-shirt, and a blazer is always a safe bet for a dude when making a dash out of the house. His hair, on the other hand, is another story. Hair combs were invented a long time ago folks!