Regarded as one of the most fashionable women in the world, Princess Kate’s royal lookbook relies on a few consistent commandments for chic dressing. Not one to stray too far from her tried and true fashion formulas, Kate often wears traditional ‘queen-in-waiting’ clothing with an emphasis on demure dressing (i.e. no cropped belly shirts, leather pants or bedazzled bustiers) and sophisticated styling.

Still, even a palace residing princess needs to switch up her wardrobe every now and then and enjoy a little fashion fantasy. Though she rarely breaks the rules sartorially speaking, once upon a time (or two), she will throw out the royal rulebook and wear something unexpected, bold or brazen.

Here are 12 of Kate Middleton’s Biggest Style Risks Ever:

1. Floral Frenzy

Wearing Erdem’s ‘Alouette’ Tiered Silk Gown, Kate brought a touch of garden glam to a black tie affair at the V&A museum in October 2015. The bold blossomed evening gown was a major risk for the princess as the Ohana Tulip print was a far cry from her solid styles and one-hued dresses. Kate went further into daring territory by opting for a sleeveless dress (a rarity in her collection of glamorous gowns).

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2. Leggy Lady

Showing off her fabulous figure and gorgeous gams, Kate dialed up the heat in this Jenny Packham high-low ‘pale jade’ cocktail gown for a photography awards gala in October 2014. The mini skirted Packham left royal watchers stammering and swooning.

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3. Emerald Enchantress

Forgoing a basic black dress or slinky column bodycon, Kate instead went full ballerina princess and stole the show in a green ‘Wonder’ gown by Jenny Packham in Jamaica in March 2022. Adorned with plenty of tulle, specks of crystal and ruffles galore, Kate took a risk by wearing a maxed out maxi.

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4. Superhero Style

Rather than play coy at the James Bond premiere in September 2021, Kate opted to go full throttle and donned a golden caped statement gown per Packham that was part superhero, part Grecian goddess. The demure duchess of yore was no longer. A powerhouse princess and new Bond girl was born.

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5. Baby Got Back

In 2015, Kate left royal fashion fans shaken and stirred with a see-through ethereal  Packham confection for the premiere of James Bond movie ‘Spectre.’ The pale blue floor length gown with its skin showcasing back was a sharp departure from the princess’ usual modest and concealing fashion fare.

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6. Velvet Crush

Frequently cited as the dress royal fans are most clamoring to see again, this mermaid  McQueen made its red carpet debut in Kate’s early Crown career. It’s sweetheart bodice and trumpet skirt was a major risk for the princess who shunned straps and sleeves in favor of major dress drama.

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7. Peter Pan Perfection

Sure, the princess often wears hearty headbands and frilly fascinators with swirls and ribbons and other decorative bobs and bits but she’s less inclined to sport fedoras for major functions. Yet, Kate took a style risk for Christmas Day 2022 wearing a Philip Treacy broad brimmed hat with a quill feather.

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8. Grape Expectations

Playing the monochrome card, Kate was pretty in purple and wore a very violet Emilia Wickstead suit set for a visit to Northern Ireland in September 2021. Kate repeated the plum menswear moment for a Shaping Us symposium in November 2023. While few could pull off Barney chic, Kate managed to look smart and sophisticated.

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9. Phantom of the Opera 

Princess Kate took a major accessories risk with her bold black elbow length Cornelia James ‘Melissa’ opera gloves (not to mention long floral statement earrings from Zara) for the BAFTAs in 2023. Giving old Hollywood glam, the dress and glove combo was such a hit that even Taylor Swift imitated the swan style a few months later. 

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10. Dynasty Duchess

Playing with pattern, print and puff sleeves, Kate brought 80s whimsy to the Caribbean in this bold yellow Alessandra Rich dress in March 2022.

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11. Vested Interest

Leaning into librarian chic, Kate made a bold and unexpected style move opting for a preppy sweater vest from Cefinn to visit a community hub in October 2023. The scholarly style was so wholesome it made us want to break out our trapper keepers and No2s.

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12. Lime Lust

In one of her most risky style moves ever, Princess Kate threw out her prim skater dresses in favor of an ultra-formfitting number from Solace London. The mom of three paired the highlighter hued dress with an emerald choker from Princess Diana’s royal jewelry collection and consequently she broke the Internet.

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