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8 of Princess Diana’s best fashion looks

Princess Diana is a name known by many. The late Princess of Wales was not only an activist, loving mother and beloved royal favorite amongst the British, but also a fashion killer. Up until her death, Diana was breaking the conservative fashion norms around her, redefining her own femininity and sensuality within the media and in her personal life.

In honor of Netflix’s new season of “The Crown,” why not list some of Princess Diana’s best fashion looks throughout her life. Here are eight iconic looks that Diana simply slayed during her lifetime:

Jan. 1, 1981: The black sheep sweater

Diana wore not only a bright red sweater, but a sweater with a black sheep surrounded by white sheep during a polo match. Obviously, this was most likely a direct dig to the monarchy itself, especially as the princess was widely sensationalized as soon as she entered the royal family. What makes this look so memorable is simply its symbolism, as well as Diana’s courage to wear the sweater. 

July 12, 1981: Yellow overalls

Unlike the royal women before her, Diana broke one of the many fashion norms during the 1980s by wearing a pair of light yellow overalls during a polo match at Windsor Great Park. Paired with a floral shirt underneath and some subtle jewelry, the look was simple, but proved that the princess didn’t need to wear a skirt or dress to embrace her femininity.

Nov. 4, 1981: A sheer purple gown

At the Victoria and Albert Museum, Princess Diana chose to wear a sheer purple gown paired with a pearl necklace and bracelet to stun the crowd. The dress, an array of purples and subtle pinks, was so revolutionary because of how informal it was. With puffy ripples and a glittery train, it’s definitely one of Diana’s most underrated looks.

Dec. 8, 1982: Red sparkles

Princess Diana arrived to watch the ballet in a sparkling red formal gown at the Royal Opera House, carrying a silver handbag and sporting her classic bob. The sleeveless dress made the princess shine amongst the rest, the red a statement color. Overall, this look proved just how bold the princess was with her style.

May 15, 1987: Sheer blue

After having her two children, Diana stepped back into the spotlight to attend the Cannes Film Festival in France. Wearing a gorgeous light blue gown, the princess matched it with a light blue scarf and emerald earrings. The dress was flowy and light, simple again, but also an amazing display of her beauty and grace.

April 25, 1989: Cowboy boots, a blazer and a baseball hat

Dropping her sons off at school, Princess Diana shocked the media when she stepped out with a blazer, sweatpants set, blue baseball hat and most unroyal of all, cowboy boots. Smirking at the paparazzi, this look was a major diss to the press, the princess simply not caring about what others thought of her.

March 17, 1993: Pretty in pink

While in Manchester, Princess Diana wore a hot pink button-down dress with black tights and heels to an event, looking radiant. The look was business casual, but also fashionable and ahead of its time and is definitely a fashion piece coming back into the mainstream again.

June 1994: The revenge dress

Last, but not least, is the revenge dress, aka arguably Princess Diana’s best look from her 36 years. At the time, Diana was divorcing Prince Charles, yet made an appearance despite the drama at the Serpentine Gallery. Made by Christina Stambolian, Diana showed up to the event in a black, knee-high velvet dress, matched with black tights and a string of pearls across her neck. All in all, the look was the ultimate act of revenge, a symbol of winning back your womanhood.


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