Lifestyle Style Jessica Simpson: My Style Timeline From all-American blonde to vixen brunette, Simpson's looks are always evolving. Click through to see her recent styles By People Staff Published on October 30, 2007 06:00 PM Share Tweet Pin Email 01 of 05 MAY 2006 Sara Jaye Weiss/Startraks As one of Hollywood’s best-known blondes, Jessica Simpson shocked the world when she popped up at the American Latino Media Arts Awards in L.A. wearing a tangerine strapless dress and a red wig instead of her signature locks. 02 of 05 AUGUST 2006 AXELLE/BAUER-GRIFFIN A couple of months later, while hosting the Teen Choice Awards, Simpson was back to long, blonde curls. With her ex Nick Lachey in the front row and his new girlfriend Vanessa Minnillo nominated, it’s best not to take any chances and go with what you know. 03 of 05 AUGUST 2006 Bryan Bedder/Getty By the time the VMAs rolled around and news broke that she was dating John Mayer, a confident Simpson was sporting a sassy blonde bob. Paired with a simple – and super short! – little black dress and glamorous earrings, she followed the adage “less is more.” 04 of 05 MAY 2007 BRIAN ZAK/GAMMA As things between Mayer and Simpson were heating up, the brunette singer hit the Metropolitan Museum of Art Costume Institute Gala in a sparkling silver dress with a plunging neckline, and replaced her usually pale lipstick with a bold red hue. 05 of 05 SEPTEMBER 2007 Gregory Pace/BEImages Back on the market and back to blonde, Simpson showed off spiraling curls and an off-the-shoulder gray dress under the tents of Bryant Park at a Michael Kors runway show during New York’s Fashion Week.