After J. Crew president and creative director Jenna Lyons, no one has been more influential in evolving the company’s fashion reputation than Obama, who wore the brand regularly during her husband’s first presidential campaign. In October 2008, amid reports of Sarah Palin’s $150,000 wardrobe budget (and just two months after Cindy McCain caught flak for an Oscar de la Renta outfit estimated to cost $300,000), Obama appeared on the Tonight Show with Jay Leno in head-to-toe J. Crew, a decision seemingly made to emphasize her blue-collar background and appeal with middle-class voters.