Princess Diana’s Popular Royal Looks RankedPublished on March 21, 2019. Updated March 2, 2020
Princess Diana became one of the world’s most influential fashion icons during her time as a Royal and even after her passing she still remains an icon and role model to this day. She constantly had all eyes on her and wasn’t afraid to experiment with bold patterns and shapes, which is why we’ll never forget many of her memorable fashion looks. While we absolutely loved Diana’s tendency to take risks with her fashion, unfortunately, this wasn’t always for the better. Follow along as we rank all of the beloved late Princess Diana’s best and worst Royal looks:
18. Best — October 1989
Princess Diana stepped out in October 1989 at the British Fashion Awards wearing a sleek white beaded dress which she paired with a sharp, bolero style jacket. This glitzy, column-style dress will forever go down as one of Princess Diana’s most memorable and fashionable looks of all time.
17. Worst — February 24, 1981
We have to admit we were a little disappointed by this look that Diana wore for her official portrait with Prince Charles to announce their engagement. There was controversy surrounding the look which claimed that Diana was not recognized by the sales clerk at the store Harrod’s and was redirected to shop off-the-rack. We simply felt underwhelmed and wish she had opted for something more memorable and special for the monumental occasion.
16. Worst — December 1992
Princess Diana stepped out in December 1992 to attend the Jester ball at the Hilton hotel. As much as we love Diana in red, we can’t say this holiday look was one of our favorites. The combination of the bold floral embellishment and heavy velvet texture felt quite overwhelming paired together.
15. Best — January 1988
Princess Diana looked absolutely gorgeous in this light pink and indigo printed dress that she wore in Melbourne on her visit to Australia during the Bicentenary Celebrations. The strapless gown featured flattering ruching along the hip and the rich, contrasting colors worked beautifully to complement her sunkissed skin.
14. Worst — February 1986
We have to admit we weren’t huge fans of this blue embellished dress that Princess Diana wore at a banquet in the Northern Portuguese City of Oporto for the 1986 Royal Tour. Her dress was designed by Catherine Walker but was significantly redesigned in 1987 and reappeared as a sleeveless evening gown with a low neckline, which we definitely preferred.
13. Best — June 1987
In the summer of 1987, Princess Diana was spotted leaving Arundal Cathedral after attending a wedding. For the dressy occasion, she donned a striking black and white polka dot dress which was absolutely iconic, especially with the perfectly coordinating fascinator. Both Meghan Markle and Kate Middleton have polka dot pieces in their current wardrobe, which we could most definitely presume was a style tip they picked up from their late mother-in-law, Diana.
12. Best — November 1992
Princess Diana was known for her beautiful pastel-colored coordinating sets, which became a signature look of her style. We absolutely love this magenta pink set she wore arriving at an Aids Information kiosk in the Latin quarter of Paris. The look felt super feminine but still sophisticated and modest.
11. Worst — April 1985
One of Princess Diana’s unfortunate fashion misses as a Royal was when she visited Pope John-Paul II at the Vatican in 1985. We can definitely appreciate the fact that she wore black as a sign of respect, but the combination of black lace and the dramatic veil felt quite heavy and overly theatrical.
10. Best — March 1985
In March 1985 Diana was photographed attending the Bruce Oldfield fashion show in aid of Dr. Barnardos. For the event, Diana donned a head-turning metallic silver gown that will always be remembered as one of her most iconic looks. It felt true to the ’80s with the structured shoulders but also transcended well as a classic throughout the generations with the elegant pleats and glamorous metallic texture.
9. Worst — August 1987
Princess Diana was spotted in August of 1987 walking at the Rothesay Highland games wearing a Scotland tartan dress. As much as we love that the Royal family dresses to honor the country they are visiting, we have to admit we didn’t love this look. The lace frill and bow along the neckline didn’t seem to fit with the heavy tartan print of the dress.
8. Best — December 1992
In December 1992, Princess Diana was spotted looking absolutely gorgeous at a film premiere for Just Like a Woman at the Odeon Cinema Leicester Square. The crimson off-the-shoulder dress was elegant, glamorous and totally eye-catching.
7. Worst — May 1981
Shortly before she married Prince Charles, Lady Diana was photographed on the royal family’s Balmoral Estate. Her outfit certainly reflected the fact that she wasn’t quite a Royal yet. From the reindeer-embellished sweater to the corduroys, a casual look like this definitely wouldn’t fly once she became an official Princess.
6. Best — February 1996
Princess Diana was spotted in February 1996 leaving Royal Albert Hall for a gala performance of La Boheme in aid of the British Lung Foundation. For the occasion, she donned a striking navy lace dress with sequin detailing throughout. She topped the look with classy pearls around her neck which really brought an air of classiness to the glitzy look.
5. Worst — June 1982
Princess Diana stepped out in June 1982 to present Prince William to the world. While we can definitely appreciate the fact that she opted for a loose-fitting dress post-childbirth, we simply didn’t love the specific dress she opted for. The combination of the bow detail, bright color, and polka dot print all felt like a little much when paired together.
4. Best — November 11, 1985
Princess Diana made heads turn back in November 1985 when she stepped out wearing this sleek one-shoulder number. We absolutely love that despite being a Princess, Diana wasn’t afraid to show a little skin and glitz in the classiest way possible.
3. Worst — May 11, 1989
Princess Diana’s affinity for bold prints and patterns was admired by many, but unfortunately, sometimes her bold style didn’t always work in her favor. This look she wore in May 1989 is the perfect example of that. From the dramatic print on the chest to the awkward ruching on the bodice, this definitely wasn’t one of Diana’s better fashion moments.
2. Best — June 1994
In June of 1994, Princess Diana stepped out in one of her most sultry looks yet in a dress that many dubbed the “revenge dress.” She donned the off-the-shoulder little black dress on the same night that Prince Charles admitted to adultery. This dress was the perfect statement-making look to wear the same evening.
1. Worst — July 29, 1981
Many are conflicted on whether they love or hate Princess Diana’s puff-sleeve wedding dress that she donned back in 1981, but we personally weren’t the biggest fans. From the voluminous sleeves to the full Princess skirt, the slender Princess seemed to get lost in all the fabric.