If you don't subscribe to the classic Summer-stripes look, then you'll love Nicole Richie's tougher take on it. You might immediately think to grab classic denim shorts and a blue-and-white striped top, but the designer mom — who's been on something of a Summer style streak — might suggest you opt for black denim and a shoulder-baring tank to make a difference. Adding to the edgier vibe, forget your sandals, and look to Fall with walkable Chelsea boots. Likewise, leave your straw tote at home and throw a cool black satchel, à la Nicole's Balenciaga, over your arm. Repeat after us: trendsetter.