The Striped Skirt Suit
Jayne Fincher/Getty; Tim Graham/Getty Images Just a year after Prince Harry was born, Prince Charles and Princess Diana embarked on their second official tour of Australia in October 1985. Princess Diana wore this striped skirt suit at least twice on the tour to attend events like the Melbourne Marathon, seen here, and on a walkabout to greet local children.
A little over two years later, Princess Diana’s older sister Lady Sarah McCorquodale wore the same suit with a white pussybow blouse underneath to visit their old school in West Health on November 12, 1987.
The Magenta Drop-Waist Dress
Peter Brooker/Shutterstock; Tim Graham/Getty Images In 1986, Princess Diana wore a magenta drop-waist dress with a short strand of pearls to visit the hospice at St John and St Elizabeth Hospital in London.
Sarah Ferguson repurposed the colorful dress as maternity wear when she was pregnant with Princess Beatrice. She’s seen here wearing it with black gloves and long gold necklaces on June 8, 1988, presenting Prince Charles with a prize after a polo match at Windsor Castle. (She wore a similar dress in yellow to the Royal Ascot a few days later.)
The Green Polka-Dot Dress
Princess Diana was a big fan of polka-dots and shared the love of the bold print with her sister. For example, Princess Diana wore a green polka-dot dress when she arrived at King Khalid International Airport in Riyadh, Saudi Arabia on November 17, 1986, for a tour of the Gulf states. She accessorized the dress with a white brimmed hat to keep the sun out of her face and white kitten heels.
Lady Sarah McCorquodale re-wore the dress with sensible white flats when she accompanied her sister as a lady-in-waiting during a royal visit to Nepal. On March 4, 1993, the two sisters were photographed together at the British Gurkha Nepal headquarters—McCorquodale in the green polka-dot dress and the Princess of Wales in a coordinating pink dress with muted green polka-dots.
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The Herringbone Tweed Jacket
Nils Jorgensen/Shutterstock; Jayne Fincher/Getty Images Shortly before she became pregnant with Prince Harry, Princess Diana attended the opening of the Park Lane Fair in December 1983, wearing a puff-sleeved tweed jacket cinched at the waist with a black belt.
At the funeral of their father, the 8th Earl Spencer, in March 1992, the Princess of Wales opted for an all-black ensemble while Lady Sarah McCorquodale re-wore the gray herringbone jacket, buttoned up to the neck with a broad-brimmed black hat for the somber occasion.
The Purple Power Suit
Kent Gavin/Getty Images; Martin Keene/Getty Images Skirt suits were basically everyday wear in Princess Diana’s 1990s wardrobe. In the early '90s, she wore this bold purple suit with a coordinating floral top underneath before giving it away to her sister.
Lady Sarah McCorquodale was later photographed wearing the gold-buttoned purple suit on a walkabout in Nottingham with the Princess of Wales on September 9, 1992. She accessorized the suit with black flats and a black top underneath, while her sister wore a similar suit in cobalt blue.
The Blue Floral Dress
Jayne Fincher/Getty Images; David Levenson/Getty Images Just before her July 1981 wedding to Prince Charles, then-Lady Diana Spencer attended her first Trooping the Colour on June 13, 1981. She wore a blue and pink floral dress with white gloves, a blouse with a frilled collar underneath, and a blue floral hat to top it all off.
She lent the ensemble to her friend Sarah Ferguson (pictured here behind Princess Anne), who wore it four years later to the Royal Ascot Races in 1985 (where she met her future husband Prince Andrew).
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The Blue Skirt Suit
Mirrorpix/Getty Images; Tim Graham/Getty Images On February 21, 1991, Princess Diana took part in a game of lawn bowling at the opening of the Glasgow Centre for the Deaf. She wore a blue skirt suit with a black collar by Catherine Walker and a white top underneath.
A year later, on March 23, 1992, her sister Lady Sarah McCorquodale borrowed the outfit and styled it similarly while on tour in Hungary.
Red Polka Dots
Anwar Hussein/Getty Images; Tim Graham/Getty Images During a walkabout on April 14, 1983, in Melbourne, Australia, Princes Diana wore a cheerful polka-dot dress underneath a red blazer.
Six years later, her sister Lady Sarah McCorquodale wore a very similar dress (if not the same exact one, just tailored differently and styled with a new collar) to her brother Charles Spencer's wedding to Victoria Lockwood on September 16, 1989, where Prince Harry was a page boy.
Lyndsey Matthews is the Destination News Editor for AFAR; previously she was a Lifestyle Editor across all of Hearst Digital Media's brands, and a digital editor at Martha Stewart Weddings and Travel + Leisure.
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