All of Princess Diana's best Royal Ascot looks over the years

By Meaghan Wray

June 14, 2021Jun 14, 2021, 10:38 AM GMT+1

Lady Diana Spencer, who eventually became known as the "People's Princess," was revered for many things including her fashion sense. Always starting trends and pushing the envelope, she had an impeccable eye for pattern, colour and detail – and some of her best outfits were spotted on the freshly cut grass at the Royal Ascot.

Often sided by her husband, Prince Charles, and one of her closest friends, the Duchess of York, Diana consistently attended the annual event, with small breaks to welcome her children Prince William and Prince Harry.

Scroll through the gallery – or click through, if you're on desktop – to see her best Royal Ascot looks through the years...

Photo: © Getty Images

1980

Then Lady Diana Spencer attended her first-ever Royal Ascot with her fiancé, Prince Charles, on June 16, 1980. She stunned in a purple-and-white checked dress, paired with lilac heels, a matching wide-brimmed hat and clutch, and white gloves.

The royal couple went on to wed a month later on July 29 at St. Paul's Cathedral in London.

Photo: © Tim Graham Photo Library via Getty Images

The following day, Diana dazzled in a grey belted number, anchoring the look with white heels and topping it off with a white cap to match. Later to be known as the "People's Princess," Diana was accompanied by her bodyguard Graham Smith, who looked handsome in a morning suit.

Photo: © Tim Graham Photo Library via Getty Images

For her third and final day at the 1981 races, Lady Diana closed it out with a fashion bang! The then 19-year-old went with a pale peach skirt and blouse number, boasting a chic white frill around the neck. She jazzed her outfit up with a three-strand pearl necklace, anchoring the look with white shoes, perfectly matching her crisp white accessories.

Photo: © Tim Graham Photo Library via Getty Images

1981

Her second year at the Royal Ascot saw a fiery red beginning! The princess wore a Bellville Sassoon outfit on June 3, 1981.

She paired a red clutch and shoes with a matching hat, and her billowing red-and-white striped sleeves underneath a longline blazer and skirt made the outfit the perfect '80s look.

Photo: © Anwar Hussein/Getty Images

1985

This year marked Diana's first time back at the Ascot since welcoming her children, William and Harry, in 1982 and 1984, respectively.

Diana made her return looking every inch a style star. Her pink outfit – crafted by designer Jan Van Velden – featured a pussy bow tie. She wore a wide-brimmed hat and beige shoes, too, carrying matching gloves in her hands.

Photo: © Tim Graham Photo Library via Getty Images

1986

Polka dots were the name of the game for Lady Diana this year! Joining Princess Anne and the Queen Mother, the Princess of Wales looked chic as ever in a white-and-black polka dot number, paired with a matching saucer hat and pumps.

Photo: © Derek Hudson/Getty Images

1986

In the prime of 80s fashion, Diana was the picture of elegance in a white button-up peplum top, paired with a white pencil skirt, heels, her classic three-stand pearls and a Somerville hat to match.

Photo: © Jayne Fincher/Getty Images

1987

What a stylish trio! Diana was joined by friends Sarah, Duchess of York, and Carolyn Cotterell, who were all decked out for the day.

Diana looked beautiful in a floral skirt suit and white hat, while her close friend Sarah brought some sunshine in a similar skirt suit silhouette, only in yellow-and-white polkadots.

Photo: © Tim Graham Photo Library via Getty Images

The royal friends put their best fashion feet forward for day two, with Diana dazzling in yellow floral print paired with teal hat and pumps, and the Duchess of York looking wonderful in green and white. The two carried umbrellas, just in case!

Photo: © Tim Graham Photo Library via Getty Images

Diana oozed cool in a black-and-white striped suit by Roland Klein and a white hat crafted by Philip Somerville. She was joined by Charles, who looked dapper as ever in a black morning suit.

Photo: © Lucy Levenson/Getty Images

1988

The Princess of Wales went with a more low-key look than her usual, pairing a Catherine Walker coat and dress with a pale blue handbag, gloves and a white Philip Somerville hat.

Perhaps Duchess Kate took after Diana's love for the British designer?

Photo: © Jayne Fincher/Getty Images

1990

The '90s were all about colour blocking, and the princess definitely got the memo.

Diana paired a double-breasted purple-and-pink Catherine Walker skirt suit with purple pumps and a matching hat. Charles wore a grey morning suit and black top hat.

Photo: © Jayne Fincher/Princess Diana Archive/Getty Images

Coordinating friends! Diana and Sarah were thick as thieves in colour-matching outfits.

The Princess of Wales wore her red blazer with a purple skirt and yellow top, while the Duchess of York was dressed in a head-to-toe red ensemble.

1991

Sarah, Duchess of York, and Princess Diana decided to coordinate yet again as they both turned heads in pastels.

Diana wore a beautiful yellow-and-white skirt suit, while Sarah stuck with a cream double-breasted number and large straw hat.

1992

For her seemingly last appearance at the annual races, Diana wore a magenta dress and matching hat as she arrived alongside the Queen Mother.

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