BEAUTY EVOLUTIONSerena Williams Loves to Experiment with Hair and Makeupby Chrystin Bunion09.26.16Both on and off the court, legendary tennis player Serena Williams, 35, is one for taking beauty risks. From teal eyeshadow to long blond braids, here’s a look back at her best looks.1March 1999AFP/Getty ImagesAt the age of 17, Serena gained global recognition in the professional tennis world as a powerful player with her sister Venus. Here, she posed fresh faced after winning the Everet Cup wearing her hair styled in her signature braids and beads.2August 2000AFP/Getty ImagesAt the 2000 US Open, Serena Williams wore her hair in a lighter color, and in a braided style. Without the beads, it was an overall more mature look.3August 2001WireImageAt the 2001 Arthur Ashe Kids’ Day, Williams wore her honey blond hair in tight, textured braids.4November 2003FilmMagicThe tennis player began to experiment with her hair and makeup a bit more off the court. At the Rising Stars Gala, she wore bronze eyeshadow, coral blush, and her hair in a new cropped bob.5January 2005Getty ImagesCelebrating her major win at the Australian Open, the tennis star rocked a simple makeup look with a pop of teal eyeliner on her bottom lashes. She switched up her hairstyle once again, now favoring curly, strawberry blonde extensions with bangs.6July 2006FilmMagicWilliams wore her honey-colored hair in soft highlights, and complimented the shade with bronzed makeup.7September 2007Getty Images for IMGWilliams looked mature at the Zac Posen in 2007, thanks to a darker hair color and shorter cut.8October 2008WireImageWilliams turned heads in a simple makeup look with straight, light brown hair at the 17th Carousel of Hope Ball.9September 2010WireImageWilliams looked chic at New York Fashion Week, thanks to sleek, slicked back hair, smoky eyeshadow, rosy cheeks and impeccable contouring.10September 2013Williams opted for a dark, bold cat eye while playing at the 2013 US Open. She looked like a complete rockstar with her thick-wavy locks pulled back into a low ponytail, and secured by aNike headband.11December 2015WireImageAt the 2015 Sports Illustrated Sports Person of the Year Ceremony, Williams wore her hair in a wavy chin-length bob with a side swept bang.12February 2016FilmMagicWilliams’ super straight hair at the 2016 Vanity Fair Oscar Party was flawless, and accentuated her enviable bone structure.