The Enduring Appeal of Tomboy Chic

The timeless allure of the tomboy – Photograph, Instagram

There’s nothing new about women wearing menswear, but it seems even more appealing than ever as we can’t seem to escape “Barbiecore.” I don’t know about you, but I am officially Barbie-d out.

Quite frankly, I want to go in the opposite direction, which is not a stretch since I’ve long subscribed to a certain “comme des garcons” in my wardrobe. It’s very freeing to find a system for dressing that goes beyond the vagaries of fashion’s ins and outs, suits you perfectly, and takes the guesswork out of the equation.

Photo courtesy of Instagram

Notwithstanding the ongoing gender diversification in fashion and continual blurring of the lines between masculine and feminine, the essential elements of a man’s wardrobe remain as relevant for women as ever, if not more so. There is a timeless appeal that never goes out of style and always looks formally correct and appropriate.

We have Yves Saint Laurent to thank.

“I wanted women to have the same basic wardrobe as men. Blazers, trousers, and suits. They’re so functional. I believed women wanted this and was right.”

Yves Saint Laurent, 1977

Women had worn suits and trousers before Saint Laurent came on the scene, but as Pierre Bergé said in 2008, “Gabrielle Chanel gave women freedom. Yves Saint Laurent gave them power.” When Yves debuted Le Smoking in 1966, it was still controversial for women to wear trousers in public.

Yves Saint Laurent Le Smoking, photograph by Helmut Newton, Vogue Paris 1975, The Helmut Newton Estate Maconochie Photography

Le Smoking was, at its heart, a garment of rebellion, androgyny, and glamour, a challenge to the status quo.

Of course, it’s no longer shocking or rebellious, and you won’t be considered a fashion renegade if you wear a tuxedo, but you will stand out in a room filled with overdressed women in cocktail dresses and ballgowns.

“A fiercely private person who avoided press and public events, Katharine Hepburn’s aversion to ‘glamour’ only made her that much more alluring.”

The Cut

Katharine Hepburn, circa 1947 – Photograph by Haynes Archive for Popperfoto

Katharine Hepburn was one of the early “female adopters of trousers.” Daring to wear wide-legged and roomy pants when her colleagues would stick to dresses with cinched-in silhouettes, Hepburn marked herself as a fierce leading lady with loafers and wide-legged slacks.

Combining androgyny with glamour, Marlene Dietrich wore masculine three-piece suits and an impressive array of hats, from fedoras to berets. The 1960s muse Francoise Hardy was the queen of Parisian chic, friends with Yves Saint Laurent and Paco Rabanne, and described by Mick Jagger as “his ideal woman” – and she did it all with a dash of tomboy style. Her love of Breton t-shirts and winged eyeliner was coupled with mod caps, slouchy trousers, and oversized overcoats.

Jean Seberg – Photo by

Ask any girl with a pixie crop who inspired her to go for the chop, and she’ll probably reference Jean Seberg at least once. The American-born actress was the queen of the French New Wave films in the 1960s, and her style – slouchy, rolled-up denim, striped t-shirts, and oversized knits – was the perfect partner to her boyish crop.

Diane Keaton as Annie Hall, left, and attending the 2014 Golden Globe Awards, Photo by kipperclothiers.tumblr

Diane Keaton’s wardrobe in Annie Hall, which consisted mainly of vintage men’s clothing, including neckties, vests, baggy pants, and fedora hats, made her an unlikely fashion icon of the late 1970s. Soon after the film’s release, men’s clothing became popular attire for women.

“Everything I wear doesn’t put me in the league of women. If I were a boy, I could look a lot prettier than a lot of boys I know”

Jane Birkin

Jane Birkin – Photo by

The queen of 1960s free-spirited style, Jane Birkin, inspired the highly coveted Hermes bag named after her. Still, Jane’s REAL fashion legacy was her bohemian attitude to getting dressed in the morning, favoring shirt and ties, boyish jeans, and caps accessorized with a straw basket.

Kristen Stewart – Photo by

Kristen Stewart is long considered the “Queen of Androgyny,” subjecting her sharp, delicate features to cigarette trousers and oversized suit jackets. Stewart can even take it one step further, scrape her hair back and wear clumpy loafers – her beauty only fuels the irony.

Amy Fine Collins wearing Thom Browne seersucker – Photograph by Matthew Foley

It’s hardly surprising that many of the world’s most iconic fashion figures, style arbiters, and women whose authoritative, sophisticated style I admire routinely borrow from the boys or add a dash of androgyny to their wardrobes.

It stands to reason that many of Hollywood’s most renowned stylists, whose job is to glamorously dress their celebrated clients for the red carpet, adhere to the essentials of a man’s uniform as the basis for their wardrobes.

Julia Roberts and her stylist Elizabeth Stewart, March 23, 2019 – Photo by

Elizabeth Stewart has orchestrated many red-carpet moments for Cate Blanchett, Jessica Chastain, Viola Davis, and Julia Roberts. Still, her personal style is more tailored and unapologetically tomboyish along the lines of Katharine Hepburn, down to her propensity for mannish footwear.

Speaking of Julia, “The Pretty Woman” is known to have a tomboyish side and a penchant for suits, as noted in an article written by Carolyn Twersky for W Magazine, October 14, 2022: “Julia Roberts Continues Her Reign as The Queen of Suits.”

Elizabeth Saltzman – Photograph by Helene Sandberg for

Elizabeth Saltzman is a stylist for some of the best-dressed stars on the red carpet, including Gwyneth Paltrow, Uma Thurman, Julia Garner, Saorise Ronan, and Sandra Oh. The New York-born, London-based stylist, former Vogue fashion editor, and Vanity Fair fashion director is the daughter of Ellin Saltzman, former fashion director of Macy’s and Saks Fifth Avenue.

Like her exceptionally chic mom (both have been inducted into the International Best Dressed Hall of Fame), Elizabeth believes that “great style is elegance and clean lines.”

Elizabeth advocates for “dead-on simplicity” to eliminate the need to waste time getting dressed. She relies on a fuss free, pared-down uniform predicted on menswear essentials: a white shirt, navy blue sweater, black velvet trousers, black velvet blazer, and a wardrobe of coats, which Saltzman cannot have enough of.

The severity of Saltzman’s look is perfectly offset by her enviable, impossibly long, straight Rapunzel-like head of hair, exceptional jewelry, and statement-making shoes and sandals. “I played and played and played, and now I’ve found my uniform. That’s the fun of age: figuring out it’s not about what you wear but who you are as a person.” Touche!

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Marilyn Kirschner

I am a long time fashion editor with 40+ years of experience. As senior market of Harper's Bazaar for 21 years I met and worked with every major fashion designer in the world and covered all of the collections in Paris, London, Milan and New York. I was responsible for overall content, finding and pulling in the best clothes out there, and for formulating ideas and stories.

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