Tomboy icons through the years

Updated 12:05 PM ET, Tue April 9, 2013
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American actress Katharine Hepburn (1907-2003) was the quintessential tomboy in style and spirit. She wore pants and kept her hair short in an era when it was considered unladylike for women to deviate from dresses, stockings and girdles. She was known for being outspoken and assertive in her career choices, political views and personal life. She famously shunned the press and refused to conform to society's expectations of women when few stars would rebel. Nixon/Express/Getty Images
While French fashion designer Coco Chanel's trademark suit and little black dress are undeniably feminine, she incorporated elements of menswear that made them comfortable and easy to wear, liberating women from the confining garments of the early 20th century. She never married but dated many, including the duke of Westminister, whose wedding proposal she reportedly turned down. She is also said to have derived inspiration from her dates' clothes, supposedly taking their blazers and tailoring them to fit her. Evening Standard/Hulton Archive/Getty Images
American actress Jean Seberg (1938-1979) helped popularize rolled-up blue jeans and French-striped sailor jerseys in the United States. The look became synonymous with tomboy style. Hulton Archive/Getty Images
English actress and singer Jane Birkin is another tomboy in style and substance, "Tomboy Style" blogger Lizzie Garrett Mettler says. To this day, Birkin flouts the glamorous Hollywood look for ripped jeans, sneakers and tousled hair, making "nondescript seem at the same time effortlessly louche and chic." True, one of the most coveted bags in the world is named for her, but it's because an Hermes executive saw her struggling to contain her belongings on an airplane. Birkin claims that she's used her bags over the years and decorated them with stickers before giving them to charity. GERARD FOUET/AFP/Getty Images/file
American actress and director Diane Keaton, pictured here in 1980, made it cool to wear ties and fedoras in the days of disco and punk. Woody Allen is said to have based his eccentric protagonist "Annie Hall" on her personality (and their relationship), including her affinity for men's vintage clothes. Hulton Archive/Getty Images/File
Through her bold sartorial stylings, Deborah Harry, the lead singer of Blondie, showed that tomboys can be sexy, too. Harry wasn't afraid to mix military fatigues with leather, denim or jewelry. She also showed that tomboy style isn't just about wearing men's clothes; it's about being independent, bold and fearless.
The bassist and founding member of the Talking Heads might not seem an obvious choice, but "Tomboy Style" blogger and author Lizzie Garrett Mettler says she has a special place in her heart for women who actually play instruments in the male-dominated field of rock 'n' roll: "There's something to be said for women who hold their own in arenas dominated by men." Tom Hill/WireImage/Getty Images/File
Musician Patti Smith also belongs to the canon of quintessential tomboys in style and substance. Before breaking into New York's male-dominated punk rock scene in the 1970s and achieving mainstream success with the Patti Smith Group, she held a job in a toy factory, dated photographer Robert Mapplethorpe, published a book of poetry and wrote for Rolling Stone. In addition to her musical chops, she taught a generation that it was possible to exude confidence and glamor in jeans, T-shirts and ties. Vittorio Zunino Celotto/Getty Images/Lancia/file
Actress Jodie Foster, left, has played tomboy roles on- and off-screen for most of her life. "She's always played the tough, rebellious roles, even as a child. She was the one who could hang with the guys," Mettler said. Need more proof? She could also ride a skateboard in loafers. Frazer Harrison/Getty Images/File
Grammy Award-winning singer-songwriter Tracy Chapman's typical onstage outfit consists of jeans and T-shirts with the occasional vest or blazer. Offstage, she lends her voice to social activism through a variety of causes related to human rights. Bryan Bedder/Getty Images/File
Actress and singer Charlotte Gainsbourg probably inherited some of her tomboy style and spirit from mother, Jane Birkin. Unlike her mother, who has said she eschews high fashion and does not own a single ball gown, Gainsbourg is a regular on the red carpet and in the front row of Fashion Week shows. But media coverage tends to focus on how little makeup she wears or how she's equally at home in Balenciaga or jeans and a sweater. VINCENZO PINTO/AFP/Getty Images/file
Singer Janelle Monáe's Twitter bio, "I feel myself truly becoming the fearless person I have dreamt of being," embodies what it means to be a tomboy in spirit. The story behind her look: During a November awards ceremony, Monáe said she sticks to her "uniform" of black and white jacket and pants to honor her mother and father, who wore uniforms as a janitor and trash collector. "This is a reminder that I have work to do, I have people to uplift, I have people to inspire," she said. Scott Gries/Getty Images/file
British model, TV host and fashion muse Alexa Chung's penchant for pairing brogues and baby-doll dresses has earned praise from the likes of Anna Wintour, Karl Largerfeld and others who consider the 28-year-old the Kate Moss of her generation. She has inspired Mulberry handbags and helped design a collection for Madewell. "All of my beauty icons are men," she said in a New York Times story. "It's all about effortlessness. It's all about looking underdone." Chris Jackson/Getty Images/file
Solange Knowles is known for DJing parties of the rich and famous, modeling, releasing two albums and writing songs for her sister, Beyonce. She has also earned considerable attention for mixing vintage and high-fashion, bold prints and colors. Jamie McCarthy/Getty Images/Charlotte Ronson/File
Jenna Lyons is credited with giving tomboy style mass appeal as president of J. Crew and through her own style choices. Whether she's on the red carpet or at a runway show, she knows how to dress up boyfriend shirts with printed pants or a silk skirt. Jamie McCarthy/Getty Images/file