Following her role as the unstoppable and irresistible Elle Woods in the Legally Blonde films, Reese Witherspoon, who had previously starred as slightly more sinister characters in Election and Pleasantville, was quickly appointed as America’s newest sweetheart. Since then, Witherspoon has come even more into her own, showing unpredictable ambition through a diversity of roles. which includes her pinnacle, Oscar-winning work as June Carter in Walk the Line, the self-destructive Cheryl Strayed in Wild, and, most recently, the gleefully short-tempered Madeline Mackenzie on HBO’s Big Little Lies. Off-screen, Witherspoon has garnered even more attention for her powerhouse-producing streak and recent venture, Hello Sunshine, which aims to project female-driven stories across multiple digital platforms. She has also branched out and incorporated her timeless style into a contemporary women’s clothing line, Draper James. Witherspoon’s brand offers pieces reminiscent of her Southern roots; knee-grazing frocks, off-the shoulder tops, scalloped dresses, printed tunics, all with vibrant color. Witherspoon is the company’s best advertisement, frequently pairing her own designs with the likes of Saint Laurent, Christian Louboutin, and Tom Ford for a prim yet modern street style moment. In honor of her 41st birthday, click through for a look back on her best looks, on and off the red carpet.