The Rule: Fitted = "flattering."
How I Break It: Fashion magazines and makeover shows love the word "flattering," but what does it mean? Well, 95 percent of the time it's a catch-all term for clothes that make you look thinner (wrap dresses that cinch at the waist, dark-rinse skinny jeans, leg-lengthening "nude" heels). What flattering should mean is "literally anything that makes you feel confident and at ease," which, in my case, is loose dresses (layered over thin turtlenecks when it's cold), oversize sweaters (sometimes from the men's department), and, lately, an enormous fleece jacket. Plus, wearing a fashion sack is like walking around with a tiny force field that ensures strangers give you an extra inch or two of personal space.