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19 of Our Favorite Princess Diana Fashion Moments

She was a style queen.
19 of Our Favorite Princess Diana Fashion Moments
IMAGE INSTAGRAM/princess.diana.forever
She was a style queen.

Her legacy reaches far, far beyond fashion, but to this day, Princess Diana remains a style icon beloved by all. Arguably one of her time's most prolific tastemakers, 2017 marks 20 years since her death, and in commemoration we've rounded up some of her best fashion moments (aside from that huge, taffeta wedding gown and the John Travolta dress, for a change!), right here.

Of course, how could we leave out the Lady Dior bag? In 1995, the First Lady of France, Madame Bernadette Chirac, gave Diana the latest handbag design by Dior as a gift. The following year, it was officially named after her!

A post-divorce Diana steps out in a lace-edged navy slip dress for a night out at the MoMA. According to Vanity Fair, "Her new evening dresses were minimalist and sexy, a look that had been taboo when she was an in-house royal."

Trust Di to make a statement at London Fashion Week. Long before anyone was stepping out in their pajamas and dressing gowns, she was already ten steps ahead!


This pale yellow checked Escada outfit came nearly 10 years before Cher Horowitz' version hit the silver screen.

Cozy casual cool in jeans, a puffer jacket, and a knit pullover.

PSA: there are reiterations of this 100% on-trend polka dot #lewk everywhere these days.

The Princess was a huge champion of all things one-shouldered. One scroll through her red carpet photos is enough proof!

It was 1982, and Lady Di was way ahead of her time in an emerald-dusted choker.

This unforgettable white bandleader-style military jacket, though!

Look us in the eye and tell us this whole outfit—belted mom jeans, white tee, and boxy, oversized blazerisn't something you'd totally wear right now.

This houndstooth skirt suit is a hands-down easy favorite. Take a tip or two on wearing loud prints from the Princess herself!

Di dons a dainty blush-hued off shoulder gown in an era when carbon-matching your shoes to your dress was totally a thing.


One reason we love Diana's style so much is because she was never afraid to take risks and push boundaries. Case in point: this full tuxedo she chose to wear while pregnant with Prince Harry.

Looking pretty in pink (topped off by the Spencer Tiara, natch). She was doing the ribboned-shoulders trend eons before anyone else!

This was one of her sexier looks that caused talk back in the day! “She knew she had great legs, and after her divorce she wanted to show them off,” said the designer Jacques Azagury.

Diana was fond of bow ties for evening and pussybow details on soft sweaters for daytime. 

Wearing an heirloom emerald necklace across her forehead as a diadem, this is one of the Princess's most iconic outfits ever. We love an innovative royalin case you didn't notice, she wore it as a choker in one of the earlier looks on this list!


Two differently-colored gloves? All our yeses. This was the eighties equivalent of today's mismatched shoes trend!

We adore this quirky sailor-inspired look!