Celebrating Katharine Hepburn's Bold Fashion Choices

Take a trip down memory lane with "Remember When?", a CNN Style series that explores iconic celebrity outfits from the past.

Katharine Hepburn, a Hollywood legend, challenged gender norms by frequently donning pants in a time when it was uncommon for women to do so. Her bold fashion choices set the stage for future generations of women who prioritize comfort and power in their wardrobe.

Who could forget the iconic outfits worn by Audrey Hepburn in her movie “Woman of the Year” or the casual two-piece look she sported in Life magazine, sitting on an armchair with a carefree vibe?

However, sticking to her own fashion choices wasn’t always smooth sailing for Hepburn, who would later be recognized as a legendary actress known for her boldness. Studio staff once went as far as hiding her pants backstage to prevent her from wearing them (she decided to go without pants until they were returned). Media outlets even criticized Hollywood women who opted for more masculine attire. In 1933, Movie Classic magazine quoted actress Constance Bennett calling women's trousers “incredible, ridiculous, and absurd.” Hepburn faced challenges for her style choices, but she remained true to herself.

The American public was uncertain about Hepburn wearing pants in the 1930s, a time when it was not common for women to do so. World War II would later make it more acceptable for women to wear pants. Hollywood historian William J. Mann noted in his 2006 biography "Kate: The Woman Who Was Hepburn" that Hepburn's choice to wear pants both on and off screen made many critics and the public uneasy and even hostile towards her.

Katharine Hepburn on the set of the 1948 movie "State Of The Union."

Katharine Hepburn on the set of the 1948 movie "State Of The Union."

MGM/Kobal/Shutterstock

In 1934, Hepburn escaped to Paris with her friend Susan Steell. Critics were harsh on her latest film “Spitfire” and her Broadway show “The Lake.” People were put off by her unique views on gender, sexuality, and fame.

Before her trip, Hepburn dressed casually, wore no makeup, and avoided being linked romantically to men. She lived with a woman, sparking rumors of her being a lesbian. She also spoke out about politics, backing Upton Sinclair in the 1934 California governor race and facing accusations of being a communist. Her movies were unconventional, showing a world where single women were in control.

Costume designer Lizzy Gardiner attended the sixty-seventh Academy Awards on March 27, 1995 in Los Angeles, CA. The Oscars, which have been honoring outstanding achievements in filmmaking for almost 75 years, are now the most well-known event organized by the Academy of Motion Picture Arts and Sciences. (Photo by Barry King/Liaison)

Barry King/Hulton Archive/Getty Images

Remember when Lizzy Gardiner stunned the Oscars in a dress made of 254 credit cards?

In the 1933 romantic drama "Christopher Strong," Hepburn portrays the character of aviator Lady Cynthia Darrington, who wears pants and engages in an affair with a married man. The film appears to challenge the traditional institution of marriage, as the neglected wife of Darrington's lover (played by actress Billie Burke) expresses that "Marriage and children make almost any woman old-fashioned and intolerant."

Mann noted Hepburn's evolution from a controversial figure to a national heroine over the years. Despite being criticized as subversive, Hepburn went on to win four Best Actress Oscars for her roles in "Morning Glory" (1933), "Guess Who's Coming to Dinner" (1967), "The Lion in Winter" (1968), and "On Golden Pond" (1981), carefully shaping her public persona throughout her career.

Katharine Hepburn plays a friendly game of tennis at the Merion Cricket Club in Haverford, Pennsylvania.

Katharine Hepburn plays a friendly game of tennis at the Merion Cricket Club in Haverford, Pennsylvania.

Bettmann Archive/Getty Images

She turned herself into “a symbol of true-blue, red-blooded Americana because she had to if she was to survive and prosper,” wrote Mann.

Style trailblazer

Hepburn’s style was part of that story.

One of Audrey Hepburn's strongest supporters in creating a new public image was Gilbert Adrian, the main costume designer at MGM from 1924 to 1941. He famously dressed Hepburn in the iconic goddess gown in "The Philadelphia Story," a look that has influenced other stars like Jane Fonda, Halle Berry, and Cate Blanchett.

Adrian recognized Hepburn's forward-thinking style and supported her preference for wearing pants by showcasing it in her films. Despite the rarity of women wearing menswear at the time, Adrian helped Hepburn break barriers, following in the footsteps of trailblazers like Greta Garbo and Marlene Dietrich, as noted by fashion historian Kimberly Truhler.

Katharine Hepburn decided to wear pants while filming the 1939 Broadway hit "Philadelphia Story." Due to the show's popularity, she was chosen to reprise her role in the movie adaptation released the following year.

In 2014, Truhler, from the fashion history blog GlamAmor, described 'The Philadelphia Story' as revolutionary in its costume design. The movie showcases not just one, but two examples of menswear, and even a third if you count her equestrian outfit. These outfits are prominently featured in the beginning of the film, which was a groundbreaking move. Initially, Hepburn faced objections from producer Joseph Mankiewicz and Louis B. Mayer for wanting to wear pants, especially in the opening scene. However, her agreement with MGM gave her significant control, proving that she was the one who truly wore the pants in their relationship.

Adrian was the designer behind the iconic velvet smoking jacket. Truhler mentioned that this piece would later inspire Yves Saint Laurent. He included the ladies' tuxedo in his collections until 2002 after introducing it in his Fall-Winter 1966 collection.

Audrey Hepburn's stylish pant-led outfits have left a lasting impact. Her combination of blue jeans or high-waisted slacks with button-down shirts is considered a classic "American look." The popularity of trousers today shows that her fashion influence extends beyond the silver screen.

Editor's P/S:

Katharine Hepburn, a true icon, challenged societal norms and embraced individuality through her bold fashion choices. By defying the conventional expectations of women's attire, she paved the way for future generations to prioritize comfort and empowerment in their wardrobe. Her unwavering confidence in wearing pants, despite facing criticism, symbolized her refusal to conform to restrictive gender roles. Hepburn's legacy extends beyond her exceptional acting career; she became a symbol of authenticity and self-expression, inspiring women to embrace their unique styles without fear of judgment.

Hepburn's journey highlights the transformative power of fashion in shaping societal perceptions. Her choice to wear pants, initially met with resistance, gradually gained acceptance during World War II as women took on roles traditionally held by men. This shift illustrates the interconnectedness of fashion and social change. Hepburn's style became a catalyst for redefining gender norms, demonstrating that clothing can be a powerful tool for challenging stereotypes and promoting equality.