Royals Princess Diana's Style: From Conservative to Chic See how the Princess transformed over the years through style By Melissa Liebling-goldberg Published on June 24, 2011 06:00 AM Share Tweet Pin Email Trending Videos 01 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/Getty The future Princess first appeared to the public in 1980 as a 19-year-old kindergarten teacher, modestly dressed in preppy pastels. 02 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/AP Diane stepped out in a coordinated hat (one of her style signatures) and pale pink suit in 1981 at the Ascot Racecourse. 03 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/AP The Princess looked regal in her Victorian-influenced lace-and-navy velvet gown at a 1981 British Film Institute dinner. 04 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/Getty Showing her support for the British designers, Diana sported a pink Donald Campbell dress with a hat by John Boyd as she visited a hospital in Australia in 1983. 05 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/Getty Conjuring images of a fairy-tale princess, Diana was demure in a chiffon Bellville Sassoon evening gown at the 1984 Royal Variety Performance. 06 of 18 THE CONSERVATIVE YEARS: 1980-1985 Tim Graham/AP The Princess paid homage to the Scots by wearing a tartan plaid dress while disembarking from the royal yacht into Aberdeen with Prince William in 1985. 07 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/AP Diana embraced a major '80s trend in a big way in 1986, turning up in bold polka dots (down to her socks!) at events in England and Japan. 08 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/AP Stepping up her fashion quotient, Diana showed off the year's big runway hit, the pouf skirt, at the Cannes Film Festival in 1987. 09 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/AP The charity-minded Princess made her British Lung Foundation sweatshirt look casually chic, pairing it with tall boots and a structured blazer at a polo match in 1988. 10 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/AP Wearing her signature pearl-and-sapphire choker, Diana showed off her toned arms and a floral gown with an oversized sash at a 1989 film premiere in London. 11 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/Corbis Diana gave a glimpse of the '90s style she would embrace (bold colors, body-conscious silhouettes and shorter locks) at a 1990 event in Hungary. 12 of 18 THE CONFIDENT YEARS: 1986-1992 Tim Graham/AP Always appropriate for the occasion, the Princess gave a nod to naval chic in her double-breasted jacket at the Royal Air Force station in Scampton in 1991. 13 of 18 THE CHIC YEARS: 1992-1997 PA Photos/Landov Wearing a distinctive halter gown, Diana dared to be bold with color at a 1992 Royal Opera performance. 14 of 18 THE CHIC YEARS: 1992-1997 Tim Graham/AP As Diana's self-assurance grew, her hemlines rose. She showed off her long legs in a short pink suit during a 1993 Manchester appearance. 15 of 18 THE CHIC YEARS: 1992-1997 Jayne Fincher/Getty In 1994 Diana cemented a memorable style moment when she entered the Serpentine Gallery in a sexy asymmetrical frock by Greek designer Christina Stambolian – on the same night Prince Charles confessed on TV that he had cheated. It was the first time as a royal that she had worn black to a public event. 16 of 18 THE CHIC YEARS: 1992-1997 Jayne Fincher/Getty The mid-'90s saw a sexier, more relaxed Diana, in dresses like this beaded Catherine Walker halter worn to the Serpentine Gallery in 1995. 17 of 18 THE CHIC YEARS: 1992-1997 Tim Graham/Corbis Diana charmed America on her first official visit since her divorce, attending a charity event in Washington, D.C., in an elegant cream lace gown. 18 of 18 THE CHIC YEARS: 1992-1997 Tim Rooke/Rex USA Setting off her fit physique and dazzling blue eyes, Diana stunned at a 1997 London performance of Swan Lake in a turquoise sheath by Jacques Azagury.