2:41
- style
- Royal Family
- August 31, 2022
Princess Diana's best fashion moments
Experts walk "GMA" through some of the princess of Wales' best fashion moments.
2:41
Speaking further to Diana's wide catalog of fashion moments, Holmes and Moran elaborated on some of her most significant looks and what made them stand out.
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For her 1981 wedding to Prince Charles, Diana wore a show-stopping ivory silk and taffeta gown that included a 25-foot long train, an estimated 10,000 pearls and antique lace passed down from Queen Mary. The dress also featured puffed sleeves and a layered, ruffled collar neckline.
\"The voluminous, frothy confection was every bit the most princess-y dress of the time, and revealed the naivete of the newly 20-year-old girl who wore it,\" Holmes said. \"This sealed the storyline of a fairytale, with the heir to the throne finding his princess.\"
Holmes also said the rapt attention paid to the famed dress may have foreshadowed the prominent role that Diana would come to play in the royal family later on.
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana2-gty-ml-220820_1661004127789_hpEmbed_2x3_384.jpg\")
Diana's famed \"black sheep\" sweater by Warm & Wonderful was a statement-making pick that she initially wore in 1981 to a polo match before her marriage to Charles. However, experts have pointed out that it was her second wear, after she was officially welcomed into the royal fold, that captured everyone's attention.
\"When she wore the same style again a few years later, which was not a repeat, but a replacement as the first sweater was damaged, she was a bonafide global superstar and fashion icon,\" Holmes said. \"It was clear she knew exactly what message she was sending as 'an outsider.' It perfectly sums up her quite clever approach to clothes.\"
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana3-gty-ml-220820_1661004754296_hpEmbed_9x14_384.jpg\")
There's also plenty of significance in what Diana didn't wear during her time in the spotlight, particularly while doing charity work.
During a 1987 visit to an AIDS clinic in London, Diana chose not to wear gloves while shaking hands with people, \"which was a huge deal at the time\" and not in line with royal protocol, Holmes said.
The late princess also refused to wear big showy hats when visiting children, and was famously quoted by Kensington Palace curator Claudia Acott Williams as saying, \"You can't cuddle a child in a hat.\"
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana4-gty-ml-220820_1661005550182_hpEmbed_2x3_384.jpg\")
Diana adored wearing bold colors and jewels when visiting children. On a number of occasions, she was seen in hard-to-miss reds, pinks and more.
Many archives also show her wearing fun necklaces that children could play with while she held them.
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana-split2-file-gty-ml-220823_1661265395981_hpEmbed_8x9_384.jpg\")
\"I loved how Diana repeated and reworked her clothes,\" said Holmes. \"There is so much attention today on 'royal repeats' and Diana was the original repeater.\"
Similar to Kate, the Duchess of Cambridge and Meghan, the Duchess of Sussex, on numerous occasions, Diana either re-wore looks or re-worked them into updated styles.
In 1989, she was photographed while greeting the president of Nigeria wearing a floral-topped Catherine Walker gown that included a full lavender skirt. A few years later, she paired the floral portion of that dress with a slimmed-down pencil-style skirt at a banquet in Seoul, South Korea.
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana-94-gty-ml-220818_1660837088323_hpEmbed_1_8x13_384.jpg\")
In 1994, Diana made major headlines for wearing a striking off-the-shoulder black dress, later known as the \"revenge dress,\" while attending a Vanity Fair party at Serpentine Gallery in London. She wore the head-turning dress on the same evening that Charles admitted in a televised interview that he'd had an affair.
\"It really was the start of a whole new era of dressing for her, unapologetic -- and I wouldn't even say it was rebellious, but it was just her way of saying, 'I call the shots now. I can wear what I want to wear and I can say what I want to say and do what I want to do,'\" said Moran.
\"I think the pure nature of how she wore it and why she wore it is really important,\" she added.
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana5-gty-ml-220820_1661018645055_hpEmbed_3x7_384.jpg\")
After her separation from Charles, experts noted that Diana's style continued to evolve in bold, fearless ways.
Moran mentioned her love for Diana's Versace mini dresses and her \"stripped back '90s minimalism\" moments.
\"It's quite glam and the fit is just insane and she's really showing off her body in a way she never did before, which I think, says so much,\" said Moran.
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana6-gty-ml-220820_1661019457674_hpEmbed_5x9_384.jpg\")
![\"PHOTO:](\"http://a.abcnews.com/images/GMA/diana7-gty-ml-220820_1661019866565_hpEmbed_2x3_384.jpg\")
Moran also made mention of Diana's many laid-back casual looks. During some of her final years before her death, Diana was often spotted wearing everything from sweatshirts and biker shorts with vibrant top coats and sneakers -- reminiscent of the ongoing \"athleisure\" trend of today, a hybrid mix of athletic and business casual wear.
Referring to one of her 1996 looks, where Diana was seen wearing a red coat with sneakers, Moran added, \"It looks like she's wearing nothing under it, which I think is so cool and shows she wanted to be a regular woman.\"
\"In a way, I also think she was quite influenced by American style in her later years and she actually visited the states quite a lot,\" she said, \"so she definitely has this savvy, New York woman image to her.\"
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