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Hollywood has long influenced mainstream fashion, using film as a powerful medium to introduce bold, new styles. Madge recently had the opportunity to talk with Joan Ammen of In Their Own League in the first installment her series “Women in Business Talk Women in Film”. We discussed classic Hollywood trendsetters who made menswear into the fashion juggernaut that it is today. Of course, we are talking Dietrich, Hepburn, and Keaton. Aka Marlene, Katharine and Diane. Movie stars who pushed the boundaries of traditional women’s fashion with menswear-inspired looks, creating iconic styles that women still emulate today.
We dive into their impact and talk about the silent film pioneers who came first. Plus, no discussion about menswear in film can leave out Audrey Hepburn’s iconic movie scene that made capri pants chic. And finally, Madge uncovers the self-proclaimed inventor of women’s trousers.
Enjoy!
The silent movie era was a time of fashion experimentation, especially in the 1920s, when androgynous looks became popular. British actress Dorothy Mackaill appeared in a tuxedo in “The Crystal Cup” (1927), embracing men’s clothing as an expression of her character’s disdain for men. This moment marked one of the first depictions of menswear on a woman in film.
Greta Garbo also created a stir with her 1929 performance in “The Single Standard“, where she wore trousers to convey her character’s rebellion against societal norms. Off-screen, Garbo preferred tailored suits and trench coats, championing simplicity and clean lines. Her style, deeply influential, brought menswear’s elegance into the mainstream.
Louise Brooks, the flapper icon with the signature bob, contributed to the rise of androgynous fashion as well. In “Beggars of Life“ (1928), she wore boys’ clothing, showcasing a more relaxed, masculine silhouette. Her mix of youthful rebellion and sophistication resonated with the Jazz Age’s evolving style norms.
Marlene Dietrich’s sartorial choices in the 1930s cemented the tuxedo as a symbol of power for women. Working with designers like Paramount’s Travis Banton and later Coco Chanel, Dietrich donned tuxedos in “Morocco” (1930) and “Blonde Venus” (1932). These striking outfits went beyond costume; they were statements of independence and confidence. Her menswear choices enhanced her many roles as a strong, intentional woman. You never saw Dietrich as a wallflower or victim.
Dietrich’s signature look—sharp lines, tailored blazers, and a confident swagger—redefined femininity. Her embrace of menswear-inspired women to experiment with traditionally male attire, reshaping fashion ideals for the modern woman.
Katharine Hepburn’s insistence on wearing trousers both on- and off-screen was revolutionary. In movies like “Christopher Strong“ (1933) and “Sylvia Scarlett“ (1935), Hepburn wore pants with ease and confidence, defying Hollywood’s expectations for women to wear gowns and skirts.
Hepburn’s collaboration with MGM’s chief costume designer, Adrian, helped shape her iconic look. Together, they crafted wide-legged trousers and crisp shirts that allowed her to embody a strong, self-assured character. Hepburn’s style encouraged women to seek comfort and freedom in their clothing, influencing American fashion’s shift toward more casual, practical attire.
Madge’s favorite Hepburn film is “Philadelphia Story“ costarring Cary Grant and Jimmy Stewart. What could be better? Kate sports several casual menswear looks.
While Audrey Hepburn was not known as a menswear icon, her dance scene in “Funny Face“ (1957) left an indelible mark on fashion. Her outfit—black skinny pants, a black turtleneck, loafers, and white socks—became synonymous with beatnik chic. Though initially skeptical, Hepburn later admitted the socks gave the look an extra pop.
Designed by her close collaborator Hubert de Givenchy, this ensemble was both chic and attainable, inspiring women to embrace simplicity. Hepburn’s look in “Funny Face” popularized minimalist style, which soon became a global trend.
Diane Keaton’s own style shone through in “Annie Hall“ (1977), where her mix of vests, ties, oversized blazers, and trousers became iconic. The look, crafted with costume designer Ruth Morley and inspired by Ralph Lauren, resonated with audiences and sparked a menswear-inspired frenzy in the late 1970s.
Keaton’s “Annie Hall” style, quirky and intellectual, offered women an alternative way to express themselves through fashion. The oversized blazers and loose trousers became symbols of nonconformity and creativity, influencing both high fashion and street style. The look proved to be timeless and is right in style today.
The adoption of menswear elements by Hollywood icons did more than just challenge gender norms in fashion; it reshaped the industry itself. By introducing masculine cuts, tailoring, and fabrics into women’s wardrobes, these actresses expanded the definition of femininity. From Garbo’s sleek suits to Keaton’s eclectic layers, menswear-inspired fashion remains a timeless trend, encouraging women to embrace both power and individuality in their style.
At the end of our conversation, Joan and Madge tipped their hat to Miss Fannie Harley, a Portland, Oregon magazine writer. Who, in 1918, strolled down Fifth Avenue sporting a bifurcated dress of her own design in broad daylight! Miss Harley came up with the design to enable more comfortable travel and created both daytime and evening looks. Dubbing them “Harleys”, her efforts created a brief fad that eventually gave way to more conventional trousers by conventional manufacturers
In an interview 30 years later, Miss Harley stilled sniffed at the word “slacks” for her feminine designs. Although Miss Harley disapproved of women dressing like men, she is quoted in the article: “a women shouldn’t be just another skirt”.
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