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.
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.
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.
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.
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.
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."
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.
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.
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.
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.
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.
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."
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.
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.
Tomboy style icons through the years
Tomboy style icons: Coco Chanel
Tomboy style icons: Jean Seberg
Tomboy style icons: Jane Birkin
Tomboy style icons: Diane Keaton
Tomboy style icons: Deborah Harry
Tomboy style icons: Tina Weymouth
Tomboy style icons: Patti Smith
Tomboy style icons: Jodie Foster
Tomboy style icons: Tracy Chapman
Tomboy style icons: Charlotte Gainsbourg
Tomboy style icons: Janelle Monáe
Tomboy style icons: Alexa Chung
Tomboy style icons: Solange Knowles
Tomboy style icons: Jenna Lyons
STORY HIGHLIGHTS
- Katherine McMillan wanted stylish shoes without the frills, so started making her own
- She's designing for women who blur the line between masculine and feminine
- Tomboy style is no longer a passing fad, "Tomboy Style" blogger says
- Some say the term tomboy is outdated
(CNN) -- All Katherine McMillan wanted in a shoe was style and comfort without the frilly bows or flowers.
She's a working mother who tends to buy men's shirts in small sizes and prefers the kinds of casual shoes made for men -- desert boots, moccasins, chukkas. She'll take a pair of shoes or a jacket in olive green or navy blue over lavender or aqua any day.
"I think a lot of my friends would agree that we don't want to look like an Easter egg when we go out," said McMillan, who lives in Minneapolis, Minnesota. "I'm all for feeling like a girly-girl but there are ways to do it without being a French poodle."
Don't get her wrong, she likes high heels and dresses, but not in pink. So when she couldn't find a pair of shoes she liked, she decided to make her own.
Hers are desert boots, moccasins and chukkas made of leather and suede with a kelly green lining to distinguish them from what the guys wear. She launched her made-to-order collection in fall 2011 under the name Mrs. P. Hicks, a nod to Pierrepont Hicks, the successful menswear accessories brand she and her husband, Mark McMillan, created in 2009.
He runs the business while she is the creative force behind Pierrepont Hicks' collection of neckties, pocket squares and bow ties, which has earned a devoted cult following among menswear bloggers and the people who read them. For Mrs. P. Hicks, McMillan is designing for women who blur the line between masculine and feminine, who gravitate toward styles traditionally associated with men: flat shoes with wide lasts, unembellished blouses and button-up shirts, unstructured sweaters and blazers, jeans and pants lacking unnecessary studs, embroidery or whiskering.
Katherine McMillan was tired of women's shoes with bows and flowers, so she designed her own.
"It's tomboy style, but that doesn't mean it's not feminine or sexy," McMillan said. "I think you feel sexy and stylish when you're wearing something you're comfortable in."
These looks have always been around, cycling in and out with the seasons, but the latest signs show they're more than just a momentary fad. Women are looking for shoes, shirts, even neckties that fit them better than their boyfriend's clothes. Also, brands are popping up to meet those demands, from the artisanal approach of Mrs. P. Hicks to mass-market retailers like Madewell and J. Crew, which have been widely credited with giving "tomboy" fashion broad appeal.
It's easy to forget the time before J. Crew or "boyfriend shirts," times when "nice girls" didn't leave home in pants. Katharine Hepburn and Diane Keaton were trailblazers, female fashion icons whose neckties and pants drew stares.
Modern style mavens Alexa Chung and Jenna Lyons show "tomboy chic" is more than a passing fashion, said Lizzie Garrett Mettler, creator of the popular "Tomboy Style" blog. Just as modern American women have won the right to vote and compete for the same jobs as men, it's nothing special for them to dress up in jeans or don a blazer.
A tomboy is more than a girl in boy's clothing, Mettler says in her blog; it's someone with an "inherent sense of confidence, rebelliousness and adventure." It's part style, part substance.
As brands continue to adapt traditionally masculine styles for the female form, "the new statement on tomboy style is that it's here to stay," said Mettler, author of the 2012 book "Tomboy Style: Beyond the Boundaries of Fashion."
Designer Sadie Beaudet was also drawn to menswear, but she didn't like the boxy fit on her body. She also didn't like how women's fashion was pulled from the racks one season and tossed a few months later, while menswear often had a timeless quality that never fell out of season.
With her fiance, she started Tradlands, a line of tailored women's shirts that incorporate masculine features, she said. It's a small collection of eight button-up shirts with a higher collar that doesn't necessarily lend itself to an exposed collarbone; the shirts have side gusset detail typically found in the workwear of the 1940s for reinforcement and brass snaps. All of their shirts are made in San Francisco, using denim and cotton sourced from the United States.
"We're trying to walk that line with a dash of feminism in the fit but clearly masculine in the details," she said.
Even the necktie is getting a feminine overhaul. What makes a lady tie? The fabric and the width, naturally, said Nashville designer Otis James.
Menswear designer Otis James models a "lady tie" that he created specifically for women.
His hand-stitched ties have earned him nods from publications like GQ and Garden and Gun. When the 29-year-old designer realized that many of his customers were women buying for their significant others, he decided to start creating products they might want for themselves.
"I'm hoping maybe they'll bring in more single women," James said, mostly joking, in an interview in his Marathon Village studio last month. "I think there's definitely a market for them."
Not everybody is comfortable with the word "tomboy." Some say the spirit of progressiveness has rendered the term archaic.
When Carmela Spinelli hears the word "tomboy," a particular look comes to mind: Strong, independent, rebellious. But the chairwoman of the fashion and accessories design department at the Savannah College of Art and Design said the description might need an update.
"To use a term that includes the word 'boy' to describe a state of independence and free-thinking for women seems kind of backward," Spinelli said. "The boundaries have changed. Women are strong and independent and have no sense of preciousness, so why would you use a term like tomboy to describe that?"
Perhaps it's because of the style's close ties to menswear. McMillan's Pierrepont Hicks is better-known, but Mrs. P. Hicks is her passion project. (Plus, she gets to keep the samples, she said.)
From the start, McMillan and her husband decided to keep their products made in the United States. That wasn't hard to do with neckties and pocket square, but it proved much more difficult for women's shoes, because so few manufacturers were equipped to do what she had dreamed up.
McMillan ultimately partnered with Maine-based mens' shoe maker Rancourt and Co., one of few shoemakers in the United States who specialize in classic men's styles similar to the ones she wanted. For her moccasins, she found another family-owned business in rural Minnesota.
With Mrs. P. Hicks approaching the two-year mark, McMillan said she has finally hit a groove and found a market.
"We even get orders from men now," she said. "They say they like the green interior."
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