17 Top Princess Diana Street Style Looks You Have Never Seen

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Princess Diana is a world-renowned personality and one of the most legendary and admired public figures in the world. The late princess of Wales was not only famous for her title, but her dressing style and fashion sense swept its way through the fashion realm and dethroned all other trends in the league. She was one of those popular personalities who not only ruled the British Royal Family but became a trendsetter of street style fashion in the 80s and '90s era. The craze and rage for Lady Diana continues to persist in the hearts of millions of people even today. From going to a polo match to stepping out of the gym to dropping kids to school, every single picture of the icon randomly clicked by the paparazzi then is considered an ideal street-style look which millions of people reckon is worth trying. 

The top 17 street-style looks of Princess Diana will take Gen X and Gen Y back to their memory lane to the time when even a single glimpse of Lady Diana was cherished. To all the Gen Z who couldn’t see the glance of the icon in pictures, newspapers and television when she was alive, these street-style looks of Princess Diana will give them the chance to opt for any similar outfit worn by the late princess. 

Take a sneak peek at Princess Diana’s street-style outfits that are worth trying out!!

The following 17 street-style looks of Princess Diana are most commonly seen and adopted by many people including celebrities. These street style outfits of the late legend are timelessly elegant and sophisticated, and most importantly, loved by many. 

Purple Sweater 

This picture of the late princess was clicked at London Park in 1980. She was seen wearing a light purple button-down top with rolled-up sleeves under a purple sleeveless sweater. She paired it with a flared white midi skirt with patterns on it. The outfit looks comfy and stylish for any outing or stepping out to carry out daily errands.  

 Princess Diana in purple sweater

                                                                                                                      IMAGE: @Amber / PINTEREST

Black Sheep Sweater 

The red color sweater with white sheeps on it looks ethereal and classy. She paired the sweater with a white collared top a small black bow, and white flared trousers. She kept her footwear simple and wore red ballet flats. She wore this outfit to the Windsor Polo Match in 1981. This sweater of Princess Diana is still worn by many people including the famous Hollywood actor Harry Styles.  

Princess Diana in Black Sheep Sweater 

                                                                                                                                                   IMAGE: @People / PINTEREST

Striped Pants 

This is one of the most stunning and sassy street-style outfits worn by the late Princess of Wales. The white button-down loose top with a round collar paired with flared blue-striped pants is perfect for a day out and also one of my favorite outfits. Diana completed the look with her iconic oversized aviator sunglasses, gold stud earrings and bracelet, and a watch. She wore the dress to the Polo match held in Sussex in 1983. 

Princess Diana in Striped Pants

                                                                                                              IMAGE: @Cosmopolitan / PINTEREST

Black And White 

Wearing an outfit with a black and white colour combination seems standard, but the way Princess Diana slayed her looks in a black sweater and white striped pants is unparalleled. She attended a polo match at Guards Club and preferred to wear a white top under a black sweater which had a circle design crossed by a horizontal line on it, and white flared pants with stripes on it. Her footwear was the usual ballet heels which she was often seen wearing back in the day.  

Princess Diana Black And White

Top And Jeans 

This outfit worn by Princess Diana will not only make you fall in love with her style but also with her sympathy and affection towards people suffering from illness. She is seen wearing a sweatshirt provided by the British Lung Foundation, which she has been supporting for a very long time. She paired it with a black coat and denim jeans. She completed the look with brown ankle-high boots and tucked her denim jeans in it. 

Princess Diana in Top And Jeans

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Jacket And Skirt

Lady Diana was seen wearing a dark green Philadelphia Eagles varsity jacket under a black top, and a dark blue pencil skirt with a belt fastening, while dropping her son Prince William and his friend to school. She paired the outfit with black sheer tights and black shoes which perfectly accentuated with her outfit and overall look. 

Princess Diana in Jacket And Skirt

                                                                                                                   IMAGE: @WhoWhatWear / PINTEREST

Yellow Jumpsuit 

Another glimpse of Princess Diana at the polo match, this time walking down with Sarah Ferguson, can be seen. Lady Diana mostly preferred to wear outfits that did not comply with the British Royal family’s rules, but she carried them with confidence. A light yellow jumpsuit, a floral button-down with a white collar, and sunglasses at the top of the head an examples of fearlessness and exude the versatility of the late icon.   

Princess Diana in Yellow Jumpsuit 

                                                                         IMAGE: @POPSUGAR / PINTEREST

Graphic Sweatshirt 

Princess Diana was known for her fearlessness in breaking the royal family’s rule and carrying her favourite outfits with style. She wore a dark blue baggy Virgin Atlantic sweatshirt and peach biker shorts while stepping out from the Chelsea Harbor Club. She completed the look with white joggers.  

Princess Diana in Graphic Sweatshirt 

                                                                                                                       IMAGE: @AMYAMIRAULT / PINTEREST

Puffer Jacket 

The princess was seen in Lech, Austria in 1994, while she was on her skiing holiday. She wore a black turtle-neck top under a red puffer jacket, jeans, and a cap to protect herself from the snowfall and the chilly breezes of the region. She paired the outfit with brown ankle-high boots, sunglasses, and a pair of gold, round-shaped earrings. This look was copied by Elizabeth Debicki as well.

Princess Diana in Puffer Jacket 

                                                                                                                  IMAGE: @WhoWhatWear / PINTEREST

 Polka-Dot Pants 

If you wish to take a glance at one of the most unusual looks of the then member of the British Royal Family, Princess Diana, then this one is just perfect for you. She was seen wearing a jacket with a blue muffler wrapped around her neck, paired with polka-dot pants and knee-high boots. This picture was clicked when she dropped her son Prince William at Mrs Mynor’s Nursery School. 

Princess Diana in  Polka-Dot Pants

Harvard Sweatshirt 

We are all familiar with the fact that Di loved to embrace common people’s lifestyles courageously. Jogging in the streets of London with a Harvard sweatshirt, biker shorts, joggers and sunglasses is clear proof of her boldness and confidence. This sweatshirt of Diana was also seen in the famous Netflix series ‘The Crown’ and was worn by Elizabeth Debicki as she played Diana. 

Princess Diana in Harvard Sweatshirt 

                                                                                                      IMAGE: @Ryan McCandless / PINTEREST

Patterned Pants 

Lady Diana was seen carrying Prince Harry in her lap while wearing a white button-down shirt underneath a pink button-down sweater which looked casual and cute simultaneously. The pink and white checkered pants paired with ballet flats are the right choice for an elegant street-style look. You can copy this look of Diana in winter as sweaters are the best ensemble for the season.   

Princess Diana in Patterned Pants

                                                                                                           IMAGE: @W MAGAZINE / PINTEREST

Polka Dot Skirt 

This outfit of Diana seemed funny but was taken seriously by the British Royal Family. Diana is seen wearing a white sweater, and white skirt with red polka dots paired with matching socks and red ballet heels. Polka dot outfits are worn by British Royal family members very frequently, which includes the late Queen Elizabeth and Kate Middleton. 

Princess Diana in Polka Dot Skirt 

                                                                                                                      IMAGE: @Pinterest

Skirt Suit 

I am sure you must have seen this look of Lady Diana as it elevates the class and royalty of the princess. Most importantly, skirt suits were worn by the princess when she paid a visit to some place and was covered by the paparazzi. She visited The British Lung Foundation in 1997 and wore a pale blue skirt suit with gold buttons, and paired it with gold stud earrings, and ballet flat shoes.  

Princess Diana in Skirt Suit 

                                                                                                                                      IMAGE: @Pinterest

Green Blazer 

Diana was spotted in London and a random click showed her sporting an olive green blazer paired with a white turtle-neck top and pants. The pants were fastened with a black belt. What makes her look more dazzling is the brown and white matching handbag which matches with her shoes. Her iconic squared-shaped sunglasses added a captivating touch to her outfit. 

Princess Diana in Green Blazer

                                                                                                                      IMAGE: @Nguynquang / PINTEREST

All-Black Dress 

As stated earlier that lady Diana was fond of wearing skirt suits during her formal visits or whenever she wanted. She sported an all-black dress, from the top to skirt to leggings to heels, and she covered herself in black. She completed her look with gold earrings which are her go-to at most places. This look of Di looks outstanding and breath-taking. 

Princess Diana in All-Black Dress

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Black Mini Dress

This is one of the most iconic and remarkable outfits of Princess Diana, which added an exquisite and alluring touch to her appearance. This outfit, as shown in the picture, is a black, off-shoulder mini dress with a flowing piece attached to her waist that adds an extra flair to the outfit. She paired the outfit with black sheer tights and black heels. The pearl necklace with a black stone added prominence to her collarbone and defined her silhouette wear. This dress is also called the ‘Revenge Dress’ because she wore it to the Serpentine dinner in 1994, on the same day when Prince Charles publicly announced his affair with Camilla Parkers. 

Princess Diana in Black Mini Dress 

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Wrap Up 

Looking at all the street-style looks and outfits of Princess Diana, I feel that she was not only a Princess of the British Royal Family who ruled by the rule book, rather she preferred to rule by the heart. She was an exemplary personality in terms of embracing her outfits, lifestyle, and personal life choices, courageously and fearlessly. She told the world that you can wear whatever you love which is evident from her outfit collections. As stated earlier, she was not only a Princess but also a fashion icon and a trendsetter for future generations. 

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