It’s been 23 years since Princess Diana tragically passed away, and although she may be gone from this world, her legacy is shining just as bright. What started as a marriage into the British Royal family and a sweep into high society ended up with Diana becoming the people’s princess. She became a national icon whose essence was defined by her compassion, beauty and style. She traveled the world, devoting her time to endless charities and notoriously destigmatizing AIDS, while constantly battling public scrutiny with her crumbling marriage and the harsh British press. All of this was said and done with her flawless style, translating a fashion story of her humility and compassion. Which ultimately won the people over and skyrocketed her into becoming the most notorious member of the royal family. Diana’s style had the ability to express her personality, reflect modern fashion trends, and tell the story of her life. 

In the summer of 1981, Diana wed Prince Charles in what is considered the pinnacle of wedding dresses. Her dress was composed of antique lace and ivory silk taffeta fabric with a 25 foot train, tulle veil, puff pastry sleeves and adorned with pearl embellishments. The dress is often referred to as the “most closely guarded secret in fashion history”, and the reveal was an event of dramatic anticipation. It was not only her grand entrance into becoming a fashion icon, but her grand entrance into the monarchy with her own secrets and troubles to guard. Throughout the fittings Diana suffered from bulimia, resulting in her dropping down four dress sizes. Still an ingenue, Diana was nervous to enter such a public world at the age of 20, which became evident in photographs, as she often bowed her head or appeared shy.

This fairytale wedding gown would be the look that set off Diana becoming the world’s most photographed woman. No matter what the event was, everyone tuned in to see what she was wearing. Diana was a chameleon; she found a way to respect and adhere to royal protocol, yet simultaneously incorporate current trends. Her style reflected the decade, mirroring the more is more approach of the 80s fashion. She was in favor of bold colors, big silhouettes, ruffled collars, and busy prints such as polka dots and florals. She would further accessorize these looks with textured fascinators, royal tiaras, and her plethora of pearl chokers. While she did try to cater to the royal protocol, Diana would break the rules now and then, all with good cause. When it came to her AIDS charities, she chose to not wear gloves as she thought it would interfere with connecting to patients, and it helped destigmatize the disease. She also made sure to wear chunky necklaces and bright colors when visiting sick children at hospitals. She curated her clothes knowing they would be interpreted as a visual text, posing the clothes as metaphors for the various charities she worked for.

One thing that differentiated Diana from the rest of the royals was her timeless street style. Her off-duty looks were relaxed and casual, reflecting her down to earth side. She was still a normal girl deep down, taking care of two children and herself. She took the unconventional royal approach to parenting and would plan their outings together, taking them to Disneyland and McDonalds, and participating in her kids’ school’s Mothers’ Day race. To perform her motherly duties in day to day life,  she chose clothes that were stylish yet practical. Diana preferred looser silhouettes as they were not as restrictive as her royal duty clothing. It was a moment where she could be stripped back and be her authentic self, rather than worrying about maintaining a proper image. This is where her style really stood out.

First things first, Diana loved to wear a jumper. Whether it be oversized, cable knit, branded with a phrase or embellished with farm animals, it was a style staple of hers. Paparazzi would often catch her leaving the gym in oversized sweatshirts, which she paired with biker shorts and chunky dad sneakers. She was doing athleisure before any of these modern influencers. A pioneer in street style, she loved classics such as straight denim jeans and baseball caps. But she would always give her own personal spin on the look with a pair of cowboy boots or yellow overalls. 

Diana’s style journey blossomed even more after her public divorce. In 1994, Prince Charles infamously admitted to his adultery in a documentary. The following day, Diana was scheduled to attend a gala in which she pivoted her previously planned look into the instantly iconic “Revenge Dress.” Again, Diana seized the opportunity for her dress to do the talking. In that moment, she was the pure embodiment of empowerment and sexuality. She sashayed in a tight black velvet off-the-shoulder number, showcasing her long legs in sheer tights. If the dress spoke, it would say “look at me now.” It was a crystal clear message that she was leaving the royal past behind and daringly setting off into her new life. She was previously in such a conservative world, but now, she had the freedom to express herself and stand out. She had control of her own narrative and no longer had to hide.

This era of Diana’s style was absolutely her peak. She truly came into her own element and was always photographed smiling and standing strong; she was a ray of confidence. Diana began to embrace shorter hemlines and form-fitting clothing. Rather than the big and bold 80’s aesthetic she previously rocked, she swiftly and smoothly transitioned into reflecting the 90s’ minimalist aesthetic. Her favorite designer at the time was Versace. This was fitting as Gianni and Diana soon became friends, and formed a fashion tour de force of classicism meets sexuality. Her clothes were chicly tailored and had a sleek appeal, all while giving a whiff of sex appeal. Watching this transition, it became clear that Diana’s personal and fashion confidence grew throughout her lifetime.

Tragically, Diana passed away during a paparazzi car chase at the age of 36. But her legacy lives on and she still remains one of the most popular royals. Even nowadays, when royals Meghan Markle and Kate Middleton are covered, the press always likes to investigate any homage or similarities to Diana. Diana had such an impact on people’s lives that she is constantly referenced for her generational impact on both the world of fashion and British culture, still residing at the forefront of the conversation. In particular, Diana’s style evolution not only reflected the changing times, but also shed a light on her personal change and growth. Her style grew in experimentation and confidence as she endured her own personal struggles and private scrutiny. She was never afraid to tiptoe the lines of royal dress code and incorporate the latest trend that season. She found a way to make everything she wore have a timeless appeal. To me, the key ingredient was that she never let the clothes wear her. Rather she wore them to write her own story, using fashion to give her a voice of empathy and compassion for the world.

Photo 1: W Magazine

Photo 2: Wikipedia

Photo 3: Vogue UK

Photo 4: Vanity Fair

Photo 5: E! Online

Photo 6: People Magazine

Photo 7: PopSugar Australia

Photo 8: Marie Claire

Share this post
Share on facebook
Share on twitter
Share on linkedin
Share on pinterest
Share on email


Spot on Princess Di article! She loved fashion and that shinned through in your article . Great job! The world and myself loved her for an unending list or reasons that stll hold true to this day. We would watch for her flawless fashion expressions no matter what event or outing she was attending. She was not afraid of color and to me that shows confidence. We all waited to see what color gown she would be wearing . With that said though no one has or will come close to looking so effortlessly cool, confident and beautiful coming off a boat in sun glasses a simple black halter top and white shorts holding a pair of white sneakers! Thank you Grace for stirring up exciting memories of a true fashion icon who will never go out of style. Throwing on a little dash of Princess Di before heading out the door or just hanging out on the couch will remind us all how unique and special we all our 🌸

Leave a Reply

You must be logged in to post a comment.