40 of Princess Diana’s Best Fashion Moments We’re Still Fawning Over

Here's Diana in the infamous post-workout sweatshirt that just sold for $53,532!

Princess Diana looks like she could be walking down a fashion runway rather than a ship's plank in this ensemble from 1984.

We get some serious Jacqueline Kennedy vibes from this pretty pastel pink number!

Diana looks beautiful in this matching hat and dress combo standing near her father-in-law, Prince Philip.

Diana looked minty fresh in this sweet suit while visiting America and greeting fans in Chicago back in 1996. Not to mention that pearl choker! 

The People's Princess' bathing suit from 1997 is wild! 

In this photo, Diana is admiring her own black dress (which was being auctioned with other outfits to raise funds for her charities) while rocking a super cute floral and sequin number. 

She looked just as sparkly and stunning as the performers from Swan Lake while greeting them at the Royal Albert Hall in 1997.

Diana looks both cozy and cool in a fluffy sweater and flowy striped dress. 

Diana clearly wasn't afraid of bold sunglasses! She keeps her eyes shaded with a pair of white aviators while touring the United Arab Emirates in 1989.

Duchess Catherine and Duchess Meghan have donned similarly stunning gowns like this pale blue dress Diana wore to the Cannes Film Festival in 1987.

Not many people can pull-off a pink and purple suit with matching hat with such ease. Plus, how cute is it that Diana, William, and Harry are all wearing double-breasted jackets for a special service for fire brigade veterans at Saint Paul's Cathedral in 1990.

How lovely is that feathered hat Diana wore while visiting Australian school children in 1983? 

A young Welsh girl gave Diana a bouquet that matched her rosy red outfit while the Princess of Wales paid her namesake country a visit in 1981.

Diana looks so chic in a blue delicately ruffled dress with a shiny metallic belt on her '83 trip to Australia with Charles.

Diana just might have upstaged the bride in the bright red ensemble she wore to a wedding just about a month before her own 1981 nuptials. 

Young Harry's silly face can't even distract from how gorgeous Diana looks in her emerald green outfit (that happens to match her youngest son's cute look, too). 

Diana was all smiles sitting next to Bruce Oldfield, who designed her beautiful crushed velvet gown, at a charity gala in 1988.

We have no doubt this casual look was still the most chic outfit of any mom checking out their son's school in 1989.

We love how Diana always had the confidence to wear such vivid colors, like this red outfit she chose for a visit to the English National Ballet School.

The boys look great, but Diana's simple yet stunning blue coat definitely stole the show as they walked around Eton College on William's first day of school in 1995.

The way Diana embraced casual wear as a royal helped pave the way for Catherine and Meghan to do the same today.

We'd like a pair of these striped pants and white flats she wore while playing around with Prince Harry in 1987.

Diana clearly loved spending time on the ocean — and always looked amazing while doing so!

We can't take our eyes off this hot pink outfit from 1983.

The knotted top of this black and white dress (with matching hat, of course) gives it an extra dash of adorable.

Diana blended in with the camo-clad army officers while on an '85 visit to Berlin.

It's hard to guess who might have been more starstruck in this photo from the London premiere of When Harry Met Sally — actors Meg Ryan and Billy Crystal, or Princess Diana?

This off-the-shoulder red dress seems to have earned Joan Collins' approval while the pair chatted at a charity event in 1990.

Diana looks effortlessly cute while enjoying a laugh with her in-laws, Prince Edward and Lady Sarah Armstrong (Chatto) in 1983.

We're suddenly craving some pink lemonade after glancing at this photo of Diana with the Queen Mother in 1992.

Diana paid homage to the country of Japan while visiting in 1986 with this "rising sun" dress.

We'd be beaming like this young boy, too, if we got to hang out with Diana — especially in this gorgeous green dress.

This tartan suit, which she wore on a 1991 walkabout in Manchester, is plaid perfection.

Ahoy, sailor! Diana and her nod to naval attire couldn't look any cuter.

This matching hat and dress ensemble definitely brought out Diana's beautiful bright blue eyes.

Her eyes shined in this darker blue outfit while visiting Liverpool in 1993, too.

We can totally see Meghan or Catherine wearing a similarly dramatic cape to a winter event these days!

Diana was all smiles in this adorable overalls ensemble while lounging in the garden of Hargrove House in 1986.

Does this vibrant pink getup remind anyone else of Mary Tyler Moore in The Dick Van Dyke Show?

William's precious alphabet coat is great, but we're even more smitten by the subtle hint of red from Diana's belt in this 1983 photo.