The Ultimate Icon: Princess Diana’s Best Looks

The Princess Diaries: As Naomi Watts prepares for her lead role in Diana, we look back at some of the style icon’s best looks. 

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    From her early pre-Windsor days to her glamorous makeovers—after her engagement to Prince Charles and again following their separation—Princess Diana was a style icon to women around the world. She had her favorite designers to guide her along the way, among them Bruce Oldfield, Victor Edelstein, Jacques Azagury, Catherine Walker, but her charm radiated to truly make her fashion royalty. Here, a few of our favorite iconic moments.

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    PHOTO: Tim Graham/Getty Images

    1981

    Diana reinvigorated the now 157-year-old brand when she wore these green Hunter Original Wellington Rain Boots ($140) with a fisherman sweater in her 1981 pre-wedding photos alongside a young Prince Charles. 

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    PHOTO: Jayne Fincher/Princess Diana Archive/Getty Images

    1981

    Her wedding to Prince Charles was epic on every level, and her dress was no exception. Designed by David and Elizabeth Emanuel, the ivory silk taffeta gown with antique lace had thousands of tiny pearls, puffed sleeves, and an attention-grabbing 25-foot train. 

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    PHOTO: Kypros/Getty Images

    1981

    With her princess-ification, Diana embraced the ‘80s shoulder pad trend alongside the Queen Mother in this red statement print and sharp matching hat at the wedding of Nicholas Soames and Catherine Weatherall at St. Margaret’s Church in London. 

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    PHOTO: David Levenson/Getty Images

    1982

    Polka-dot superfan Diana wore this loose green dotted frock when she brought Prince William home from the hospital. Kate Middleton wore a similar-hued Jenny Packham with polka dots—a sweet homage to the mother-in-law she never got a chance to meet—as well when she and Wills brought an infant Prince George home from the hospital early this year. 

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    PHOTO: Jayne Fincher/Princess Diana Archive/Getty Images

    1982

    Only a few months after giving birth to William, Diana wowed in a Bruce Oldenfield drop-waisted, one-shoulder blue crepe-de-chine dress with ruffles at London’s Guildhall. She paired it with a pearl choker and bracelet.

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    PHOTO: Tim Graham/Getty Images

    1995

    This bright tartan suit, accented by a hot pink scarf (and an adorable Prince William), was a cheeky nod to her visit to Aberdeen. 

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    PHOTO: Tim Graham/Getty Images

    1995

    Another of Diana’s one-shouldered stunners, this turquoise dress made waves not only for its tight bodice and bold bow, but for Diana’s creative accessorizing. She turned the diamond and emerald choker—a wedding gift from the Queen—into a bold headband.

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    PHOTO: Jayne Fincher/Princess Diana Archive/Getty Images

    1995

    The perfect gown for a red carpet visit to the premiere of the James Bond film, A View To A Kill, this wide shouldered gold lamé dress was another Bruce Oldfield creation. (It also helped to earn her the nickname “Dynasty Di.”) 

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    PHOTO: Tim Graham/Getty Images

    1988

    A rare casual moment finds Diana in jeans, a British Lung Foundation tee, a blazer, a baseball cap, and funky ‘80s boots at the Guards Polo Club. 

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    PHOTO: Tim Graham/Getty Images

    1989

    The Princess wore this Catherine Walker white silk crepe dress (commissioned for Diana’s official visit to Hong Kong in 1989) to The British Fashion Awards. Because of the fluted collar on the pearl and sequined bolero, this is often referred to as “the Elvis Dress.”

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    PHOTO: Tim Graham/Getty Images

    1990

    This contrasting hued black, red, and white houndstooth suit, which Diana also wore to the christening of Princess Eugenie, was a true fashion moment.  

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    PHOTO: Jayne Fincher/Getty Images

    1994

    Dubbed the “revenge dress” by the press, this off-the-shoulder LBD turned heads at the Vanity Fair party at the Serpentine gallery; designer Christina Stambolian certainly knew she was helping Diana make the ultimate statement.

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    PHOTO: Tim Graham/Getty Images

    1997

    Diana donned this ice-blue beaded Jacques Azagury for the opening of “Swan Lake” at Royal Albert Hall. She paired it with a pearl and diamond necklace by Garrard. (Fun fact: This is the dress Naomi Watts wears on the posters for the film Diana.)

EXPLORE: Bruce Oldfield, Victor Edelstein, Jacques Azagury, Catherine Walker, Celebrity, Princess Diana, celebrity style, Best Of, Celebrity Style
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