How Princess Diana’s Fashion Has Stood the Test of Time

How Princess Diana's Fashion Has Stood the Test of Time

Princess Diana’s fashion choices continue to be iconic and influential, even decades after her passing. From her bold red knit sweater with white and black sheep to her hand-embroidered wedding gown, Diana broke royal tradition with her unique and expressive style.


The influence of Princess Diana’s fashion style remains dominant over two decades since her unfortunate passing.

The late Lady Diana Spencer, who tragically passed away in August 1997 at the young age of 36, has indelibly influenced pop culture through various shows and films such as “The Crown,” “Spencer,” and “The Princess.” These productions have explored her groundbreaking redefinition of the princess role, her defiance of traditions, and her enduring legacy as a fashion icon.

Eleri Lynn expressed to Vanity Fair in 2017 that “She went beyond fashion trends and epitomized an extraordinary level of chicness and elegance. Her presence overshadowed the clothes, making them secondary to who she was and what she accomplished.”

Just as noteworthy as these iconic outfits are Diana’s: comparable to Marilyn Monroe’s white halter dress from “The Seven Year Itch,” Audrey Hepburn’s black evening gown in “Breakfast at Tiffany’s,” and Jacqueline Kennedy’s pillbox hats and oversized sunglasses.

A few of her iconic ensembles are the notoriously vengeful red carpet gown, her casual biker shorts and oversized sweater, the classic pie-crust blouses, and her black sheep sweater.

I can’t help but be captivated by her impeccable sense of style, where even her accessories leave a lasting impression. She playfully referred to her clutches as “cleavage bags,” skillfully positioning them against my chest whenever she stepped out of a vehicle. Her affinity for chokers and wearing necklaces backward added an intriguing layer to her overall look.

How Princess Diana's Fashion Has Stood the Test of Time

Before earning the title of a trendsetter, one is still in the process of discovering their unique style. The late royal was once known as “Shy Di” due to her earlier modest outfits.

“When I initially encountered Lady Diana Spencer, as recounted to Vanity Fair, she was dressed in her debutante attire from 1979 – an ensemble characterized by its frills, lace, and a significant contrast to the trendsetting persona she would later adopt.”

And yet it’s clear that the more Diana evolved so did her approach to fashion.

As an avid admirer of fashion history, I can’t help but notice how dramatically the frills and ruffles of early romantic style began to fade around the 1980s. The museum curator is absolutely right on this – the silhouette started to streamline and sleek down during that era.

How Princess Diana's Fashion Has Stood the Test of Time

Back in 1980, during a polo match, Diana made a subtle yet powerful statement through her attire. She donned a bright red knit sweater adorned with white and black sheep, sending a clear message to the audience. This thought-provoking outfit was interpreted as Diana expressing feelings of isolation or being the odd one out.

Despite her true intentions behind it, the Warm & Wonderful sweater instantly gained popularity among people. Not long after, the label teamed up with Sperry to incorporate the design onto their footwear, underscoring the enduring influence of the princess.

At her 1981 royal wedding, Diana left onlookers in awe with her stunning 25-foot train adorned with intricate hand-embroidery featuring sequins and pearls.

Designer David Emanuel shared with TopMob News in 2021 that creating a subtle, understated gown for “her” was not feasible. Instead, he recalled the grandeur of the event and the merriment they experienced together.

A noteworthy fashion moment from the ’80s was a blouse featuring bold polka dots and voluminous puffed sleeves with an alluring peek-through neckline. This trendy attire made an appearance at a polo match, and was later revived by the late Virgil Abloh in 2017 for Off-White’s spring/summer 2018 collection, alongside other iconic Diana looks.

The designer expressed to British Vogue at that point, “She had a robust personality. Her unique style deviated significantly from the expected attire. It served as an inspiring source.”

How Princess Diana's Fashion Has Stood the Test of Time

Princess Diana’s appearances may appear familiar to us now, but several of her fashion selections defied royal conventions at the time.

Eleri noted that she was the initial royal family member captured in trousers at evening functions. However, she frequently paired this with tuxedo jackets and bowties, creating an unexpectedly daring and amusing appearance for a princess.

When Diana chose to don a black ensemble, she broke the mold and expanded the boundaries of acceptable attire for royals. Previously, black had been exclusively used during mourning periods.

Certainly, the most memorable black outfit of hers was referred to as the “revenge dress.” This controversial design, which featured a form-fitting silhouette, deep off-the-shoulder neckline, and a short hemline, was rather daring for the era. Additionally, it served as a bold statement towards Prince Charles III (then a prince and her former husband).

At the Vanity Fair fundraiser that very day, she donned the bold Christina Stambolian design despite the revelations of Charles’s scandalous interview about their marital issues and infidelity.

How Princess Diana's Fashion Has Stood the Test of Time

She had another stylish comeback up her sleeve, frequently stepping out of the gym wearing bulky sweaters and cycling shorts to thwart paparazzi from exploiting her images. In her perspective, if she repeated the same look, the worth of those photographs would diminish.

Despite her plan, the off-duty style remains popular among celebrities and influencers. For instance, Hailey Bieber paid tribute to this trend in Vogue Paris 2019, posting on Instagram, “Giving credit and inspiration to the stunningly beautiful and iconically stylish Princess Diana.”

No matter what the situation was, Diana made conscious choices when it came to her attire. At children-centered events, Eleri observed that Diana would wear vibrant outfits to give off a friendly and accessible vibe.

Eleri shared an insight about the woman: “This woman didn’t use gloves when interacting with people for her preference of direct contact. She adorned herself with bulky jewelry that kids could enjoy playing with. Over time, she stopped wearing hats to children’s hospitals due to believing it impedes the ability to give a warm hug.”

The museum guide commented, “During her hospital visits for the visually impaired, she’d usually don velvet to feel warm and to explore its textured surface.”

How Princess Diana's Fashion Has Stood the Test of Time

The fashion influence of Princess Diana, who preceded Kate Middleton and Meghan Markle in the royal family, extends beyond the realm of royality. Notably, Rihanna, Hailey, and Emily Ratajkowski have acknowledged her as their personal fashion inspiration.

In an interview with Harper’s Bazaar in September 2022, Hailey shared her admiration for a woman who stood out as the most-watched and influential figure in terms of style at that point in history. Remarkably, this trailblazing individual didn’t let her prominent position hinder her self-expression through fashion.

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2024-07-14 18:20