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Princess Diana's 50 Best Style Moments Ever
Celebrity

Princess Diana's 50 Best Style Moments Ever

The outfits that made her an icon

princess diana

By Annabelle Fernandez - published

The outfits that made her an icon.

Innately tied to her memory is Princess Diana's fashion sense, which changed as she grew into her role as as a beloved public figure. In honour of her birthday, we look back at 50 of her chicest outfits.

From: Marie Claire US

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BBTB. (Bring Back the Bolero. Please sign my petition.) Photo: Getty
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Princess Diana, Prince Charles

Regal. Statuesque. Photo: Getty
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Princess Diana

Versus an interesting juxtaposition—even just in her sartorial choices, she grew so much in a few years. Photo: Getty
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Princess Diana

Even in costume—at a Canadian barbecue, no less—she looked like a queen. Photo: Getty
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Princess Diana, Prince Charles

The sheerness makes this feel really fresh. Photo: Getty
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Princess Diana

The sheerness makes this feel really fresh. Photo: Getty
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Princess Diana

So '80s, kind of frivolous, but still marvellous. Photo: Getty
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Princess Diana

Love a drop waist. Photo: Getty
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Princess Diana

It might not be your first guess, but red was definitely one of Princess Di's best colours. Photo: Getty
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Princess Diana

If it isn't there already, this fire Christina Stambolian number will live in the "fashion" section of your brain forever. Phew. Photo: Getty
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Princess Diana

Not what you expected, eh? That's what makes it so great and modern, as the celebrity-off-duty look in beta. Or alpha. Princess Diana
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Princess Diana

Raise your hand if you're having an extremely rough time deciding whether '80s or '90s Diana is the best. Photo: Getty
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Princess Diana

This COLOR. Photo: Getty
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Princess Diana, Prince Charles

Sequins by Catherine Walker. Photo: Getty
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Princess Diana

Nice colour, nicer accessorizing. Photo: Getty
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Princess Diana, Prince Charles

I love this period in her style. Too chic. Photo: Getty
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Princess Diana

Ideas in styling: Wearing a necklace as a headband and a massive bow on your shoulder. Photo: Getty
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Princess Diana, Prince Charles

Before it all began. Photo: Getty
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Princess Diana, Prince Charles

Versus near the too-soon end. Photo: Getty
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Princess Diana

Top 10, for sure. Photo: Getty
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Princess Diana

And now, let us admire some headwear, starting with schooner of a hat. Photo: Getty
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Princess Diana, Prince Charles

Not an ad for Yves Saint Laurent, but very well could be. Photo: Getty
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Princess Diana

And this jaunty, feathery chapeau. Photo: Getty
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Princess Diana, Prince Charles

This confection is by Murray Arbeid; the crown is by the monarchy. Photo: Getty
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Princess Diana

How could we not include her wedding gown, with its tremendous train? Photo: Getty
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Princess Diana, Prince Charles

Few women could pull off powder blue hip pads, but somehow, she does. Photo: Getty
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Princess Diana

The event might've been boring, but the dress is not. Photo: Getty
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Princess Diana

She could've only worn halter-neck dresses in different colours and fabrics, and we still would've made this gallery. Photo: Getty
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Princess Diana

A maternity gown straight out of Dangerous Liaisons. Photo: Getty
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Princess Diana

And the baby himself, welcomed in pink. Photo: Getty
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Princess Diana

Somebody has to have made this into a poster, right? Photo: Getty
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Princess Diana

Ah, the "Elvis dress," designed by Catherine Walker. Photo: Getty
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Princess Diana

Another wonderful evening option, this one with an off-the-shoulder neckline and yards of pink satin. Photo: Getty
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Princess Diana

Another Catherine Walker creation with ultra-flattering ruching at the waist. Photo: Getty
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Princess Diana

Romantic florals for a performance of Romeo and Juliet. Photo: Getty
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Princess Diana

Sharpen up that resolution, and this photo could be from yesterday. Photo: Getty
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Princess Diana

Wearing Catherine Walker on a visit to Saudi Arabia. Photo: Getty
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Princess Diana

Zandra Rhodes. Trompe l'oeil. Gold. Photo: Getty
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Princess Diana

"Epic" and "paisley," two words you never really see together. Photo: Getty
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Princess Diana

The best of '80s campiness. Photo: Getty
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Princess Diana

Star power—and her secret "cleavage bags"—in action. Photo: Getty
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Princess Diana

The power of the print. Photo: Getty
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Princess Diana

See what we mean about red? Photo: Getty
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Princess Diana

But our very favorites might be the ones in simpler silhouettes, which she tended to favour later. Photo: Getty
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Princess Diana

Goodbye (from Nancy Reagan too). And thank you. Photo: Getty
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Princess Diana

Though velvet is never a bad idea. Photo: Getty
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Princess Diana

See—more velvet. (Bruce Oldfield ain't bad either.) Photo: Getty
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Princess Diana

Wowza. Photo: Getty
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Princess Diana

How is this real? Photo: Getty
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Princess Diana

The original end-of-the-night, into-the-car pap shot. Photo: Getty
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Princess Diana

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Prince CharlesPrincess DianaStyleStyle Files
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