1

Pretty in Pink

Diana at Highgrove
Tim Graham//Getty Images

Princess Diana always turned her head no matter what she wore—take this outfit, for example. She’s pictured sitting on the steps of her country home wearing pink plaid pants, a rose-colored crewneck sweater, and a pair of ivory ballet flats. Gorges.

2

Light Blue Hue

diana at polo
Princess Diana Archives//Getty Images

The princess wore blue and white seersucker pants, a flowy white blouse, and a gorgeous embroidered handbag while out and about at a polo match. Her tinted shades add the perfect amount of edge to the breezy outfit.

3

Cropped and Casual

invictus games 2020 day 1
Karwai Tang//Getty Images

Meghan, Duchess of Sussex, combined two unexpected wardrobe staples—a cropped gold-buttoned coat and faded blue jeans—to create an effortlessly cool ensemble. Her pulled-back hair and white t-shirt also added a layer of laidback luxury to the look.

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4

Belted Beauty

Diana Angola
Tim Graham//Getty Images

Princess Di accessorized a simple white and khaki ensemble with a brown leather belt, suede loafers, and cat-eye sunglasses. This chic look is still totally on-trend today.

5

A Breath of Fresh Air

the duke and duchess of sussex visit tonga day 2
Samir Hussein//Getty Images

Markle chose a pop of color when she paired a sky-blue ankle-length dress with light blue heels. Prince Harry’s steel-gray suit and blue-toned tie seamlessly matched the duchess’s relaxed outfit.

6

Royal Blue

the prince and princess of wales mark world mental health day day 3
Samir Hussein//Getty Images

Speaking of blue, Princess Kate slipped on a royal blue blazer with dark denim jeans and white tennis shoes for this outing. You can easily recreate this pairing at home using clothing items you might already have. Feel free to swap the white tee for a blue blouse for a modern monochrome look.

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7

Princess Prints

princess diana retrospective
Anwar Hussein//Getty Images

Princess Diana always knew how to work a print. She’s pictured here wearing a patterned black and white top with voluminous sleeves and a high neckline.

8

Smooth as Butter

princess diana retrospective
Anwar Hussein//Getty Images

The Princess of Wales effortlessly combined a crisp pale yellow top with pleated trousers and gold-hued shoes here. Her perfectly coiffed hair and thick leather belt proved to be the best accessories for this laid back look.

9

A Stroll in Stripes

princess margaret, the younger sister of britain's
DALMAS//Getty Images

Princess Margaret, Queen Elizabeth’s younger sister, took a stroll with her husband along the water dressed in a striped floral frock accessorized with a baby blue hair bow and white flats.

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10

Shades of Blue

the prince and princess of wales visit northern ireland
Max Mumby/Indigo//Getty Images

Princess Kate waved to onlookers in an all-blue outfit consisting of a silky blue blouse, a blue knee-length coat, and bright navy bottoms. Her laidback, wavy hair and minimalist jewelry let the effortlessly cool ensemble shine.

11

Polka Dotted Princess

princess diana retrospective
Anwar Hussein//Getty Images

Here, Princess Diana rocks another patterned outfit—polka dots. The red and white head-to-toe ensemble included polka-dotted socks, a matching pleated skirt, and an oversized color-blocked sweater.

12

Shorts Suits

invictus games
Chris Jackson//Getty Images

Markle wore a black and white shorts suit with matching ballet flats and tousled tresses at this appearance. How chic!

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13

All White

invictus games the hague 2020 reception
Chris Jackson//Getty Images

Markle sported a sleek, all-white tailored outfit while attending a reception. Her matching white bag with gold-toned hardware and sophisticated gold watch tied the look together.

14

Sweater Weather

the princess of wales visits vsi razom community hub
Chris Jackson//Getty Images

Even Princess Kate loves a good sweater vest. She paired hers with matching gray wool trousers, a cuffed white blouse, and a pair of mushroom-hued flats with sweet bow details.

15

A Maroon Moment

celebrity sightings in new york city september 24, 2021
Gotham//Getty Images

Meanwhile, for a trip to New York City, Markle embraced a monochrome maroon ensemble, which included pointed-toe heels, draped slacks, and an oversized overcoat.

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16

A Laidback Look

invictus games
Chris Jackson//Getty Images

A fan of neutrals, Markle stunned in a belted beige number while at the Invictus Games with Prince Harry. His crisp white button-down shirt and creased tan pants pair seamlessly with her elegant outfit.

17

Athletics

britain's princess of wales departs her london hea
JOHNNY EGGITT//Getty Images

Although Princess Di was often snapped in elaborate gowns and eye-catching pantsuits, she was also famous for her low-key biker short outfits. She’s pictured here showing off an orange pair matched with an oversized sweatshirt, thick white socks, and sneakers.

18

Gorgeous Gingham

the princess of wales visits the windsor family hub
Chris Jackson//Getty Images

Princess Kate always manages to style a blazer to perfection. In this photo, she wears a gingham one matched with cropped navy pants, black pointed heels, and a simple white shirt.

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19

Cute in Khaki

the duke and duchess of sussex visit johannesburg day one
Pools//Getty Images

Markle wore khaki yet again during a visit to Johannesburg. This time, it was a sleeveless collared dress with a matching belt and side pockets. Her off-white nail polish was an excellent highlight.

20

A Lilac Look

lady diana at kindergarten where she works
Tim Graham//Getty Images

Princess Diana posed for a photo in an Ivy League-esque outfit consisting of a violet-colored sweater vest, a textured skirt, and open-toed heels. She was just 19 at the time.

Lettermark

Brittany is a freelance writer based in her hometown of New York City. She writes about everything from fashion and beauty to food and wellness. When she’s not writing, she can often be discovered at her local library, playing with her cats, or exploring the Metropolitan Museum of Art.

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