Style

Olivia de Havilland’s style evolution: ‘Gone With the Wind’ to ‘The Heiress’

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Olivia de Havilland, star of “Gone With the Wind” and one of the last remaining actresses of Hollywood’s “Golden Age,” died on Sunday at the age of 104. A two-time Oscar and Golden Globe winner, the British-American beauty enjoyed a silver-screen career (and a number of headline-making scandals) that spanned six decades. She was also a bona fide fashion icon, with a particular fondness for the designs of Christian Dior; in 2019, some of her personal haute couture was sold at auction, fetching nearly six figures in total. Ahead, take a look back at some of De Havilland’s most glamorous style moments through the years.
Olivia de Havilland, star of “Gone With the Wind” and one of the last remaining actresses of Hollywood’s “Golden Age,” died on Sunday at the age of 104.

A two-time Oscar and Golden Globe winner, the British-American beauty enjoyed a silver-screen career (and a number of headline-making scandals) that spanned six decades.

She was also a bona fide fashion icon, with a particular fondness for the designs of Christian Dior; in 2019, some of her personal haute couture was sold at auction, fetching nearly six figures in total.

Ahead, take a look back at some of De Havilland’s most glamorous style moments through the years. Getty Images
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In 1935, de Havilland posed in a one-piece swimsuit and heels in Los Angeles.
In 1935, de Havilland posed in a one-piece swimsuit and heels in Los Angeles. Getty Images
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Looking impossibly chic in form-fitting knits in 1935.
Looking impossibly chic in form-fitting knits in 1935. Getty Images
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Squeezing into the backseat of a convertible in full riding gear in 1936.
Squeezing into the backseat of a convertible in full riding gear in 1936. Getty Images
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In 1938, de Havilland posed in a frothy, full-skirted tulle frock.
In 1938, de Havilland posed in a frothy, full-skirted tulle frock. Getty Images
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And made riding a bike in a pencil skirt and heels look downright simple.
And made riding a bike in a pencil skirt and heels look downright simple. Getty Images
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Dripping in feathers during a Warner Bros. portrait session in 1938.
Dripping in feathers during a Warner Bros. portrait session in 1938. Getty Images
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The actress earned the first of her five Oscar nominations for her role as Melanie Hamilton in 1939's "Gone With the Wind." Here, she poses for a publicity still in her character's period costume.
The actress earned the first of her five Oscar nominations for her role as Melanie Hamilton in 1939’s “Gone With the Wind.” Here, she poses for a publicity still in her character’s period costume. Getty Images
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Making the most of her gauzy black gown in 1940.
Making the most of her gauzy black gown in 1940. Getty Images
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Lounging with a cigarette and beer in 1942, clad in a printed silk blouse and towering Mary Jane heels.
Lounging with a cigarette and beer in 1942, clad in a printed silk blouse and towering Mary Jane heels. The LIFE Picture Collection via
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In 1946, de Havilland married author Marcus Goodrich — the first of her two husbands — in a printed dress, elbow-length gloves and an elegant hat.
In 1946, de Havilland married author Marcus Goodrich — the first of her two husbands — in a printed dress, elbow-length gloves and an elegant hat. Getty Images
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The star won her first Best Actress Oscar in 1947 for "To Each His Own," dressed in a strapless pale green gown by Ann Lowe.
The star won her first Best Actress Oscar in 1947 for “To Each His Own,” dressed in a strapless pale green gown by Ann Lowe. Getty Images
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De Havilland later took home the same statuette in 1950 for her work in "The Heiress." At the ceremony, she dazzled in a white embellished gown by Orry-Kelly.
De Havilland later took home the same statuette in 1950 for her work in “The Heiress.” At the ceremony, she dazzled in a white embellished gown by Orry-Kelly. The LIFE Images Collection via G
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The actress donned a Christian Dior wedding dress for her 1956 film "The Ambassador's Daughter."
The actress donned a Christian Dior wedding dress for her 1956 film “The Ambassador’s Daughter.” Gamma-Rapho via Getty Images
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De Havilland never lost her sense of style, seen here beaming in a Dior caftan in London in 1971.
De Havilland never lost her sense of style, seen here beaming in a Dior caftan in London in 1971. Getty Images