Ever since Diana Spencer, Kate Middleton, and Meghan Markle entered England’s royal family and became princesses and duchesses, photographers have captured their every move. However, few people have seen these rare images of Diana, Kate, and Meghan before they became royals.
Before They Were Royals
50. Kate Makes Her Debut
June 2005 was a big month for Kate Middleton. She and Prince William made their relationship official by attending the high-society wedding of Will’s best friend Rose Astor. Middleton made her mark by pairing a chic white blazer with a patterned pencil skirt and completing the look with an incredible black fascinator.
49. Diana Meets Her Dark Double
Princess Diana and Grace Kelly are both beloved blondes who married royal princes, and then sadly perished in horrific car accidents. They’ve often been compared, but few people realize that they actually met in real life. Back in 1981, when Diana was newly engaged to Prince Charles, she attended an event where she chatted with Kelly.
The Hollywood icon reportedly gave Diana some advice about becoming a princess. She quipped, “Don’t worry, dear, it’ll only get worse.”
48. Kate Looks Pretty In Pink
Kate Middleton has always been a style icon. Back in 2006, she supported a new luxury designer store called Bluebird by attending their launch. In this photograph, she oozes good vibes with a champagne glass in hand and an adorable pink ensemble. She layered a soft velvet blazer over a sweet floral dress, and completed the look with a statement bag and a dainty necklace.
47. Meghan Suits Up
Before she became the Duchess of Sussex, Meghan Markle was best known for acting on the hit legal drama Suits. Before Markle landed a major role in Suits in 2011, she’d booked a string of minor roles and worked as a model on a gameshow to make ends meet. Suits was her big break and she was not going to let it pass her by. Here she is at a TCA party celebrating the show’s success with her cast mates.
46. Kate Attends A Scandalous Wedding
Did you know that Camilla Parker Bowles‘ daughter married an ex-underwear model? Me neither. This snap shows Kate rocking a fabulous fascinator at Laura Parker Bowles’ scandalous nuptials to Harry Lopes in 2006. Kate attended the event with her beau, Prince William, who must have been proud to have Middleton on his arm. That cream coat fits her like a dream.
45. Diana Breaks The Mould
After finishing school, a teenage Diana moved to London, where she did something that would make the royal family gasp. She took a series of low-paying jobs. She worked as a dance instructor, a nanny, a playgroup pre-school assistant, and even did some cleaning work. That helps explain why she was so refreshingly different from the hoity-toity royal family that surrounded her.
44. Kate Supports a Heartbreaking Cause
Kate looks like she’s having the time of her life in this sequinned, retro halter, bright pink bag, and yellow hot pants, but she’s actually attending a heartbreaking fundraiser. The Day-Glo Midnight Roller Disco honored Middleton’s dear friend Thomas Waley-Cohen, who sadly died of bone cancer when he was just 20 years old. After his passing, Waley-Cohen’s friends honored his memory by organizing a night of fun and hope.
43. Meghan Hits Her Mark
By 2015, Meghan Markle was a bonafide TV star. In this 2015 photo, she poses for the cameras, showing off her sleek low ponytail, dazzling smile, and luxurious brocade dress. Markle didn’t know it at the time, but in less than a year, she’d start dating Prince Harry—and her entire world would change overnight.
42. Diana Looks Into the Future
As a little girl, Diana didn’t have a particularly happy home life. Her parents would divorce when she was 12 because of affairs and even physical abuse. But in this photograph, which was snapped on Diana’s seventh birthday, she seems happy and well. The future princess is visiting London’s Cadogan Place Gardens, and looking adorable while posing on the outer gates.
41. Kate Serves Blair Waldorf Vibes
Watch out, Blair Waldorf. Kate Middleton is coming to steal your look. In this 2006 snap, Kate’s smart outfit matches her posh setting. As she trots around London’s affluent Richmond neighborhood, Middleton looks chic in a classic white button up, prim cable-knit sweater, and tweed mini-skirt. The suede low-heel boots were a staple for Kate; she was captured wearing them multiple times in the mid-00s.
40. Diana Enters The Arena
A Goldsmiths Hall charity concert was the venue for Princess Diana’s very first official public appearance in 1981. But even at her first major event, Diana refused to be timid. She’s already pushing the royal family’s prim limits in this photo with her revealing neckline. As you can see tell from the mob of eager photographers behind Lady Di, the press is loving the new royal on the block.
39. Kate Struts Her Stuff
Kate loves a great red coat, so her commitment to dry cleaning such a garment is not to be doubted. Here she is on the day before her 25th birthday, doing what needs to be done to keep that cherry-red jacket bright. In this 2007 snap, Kate prances about London in a monochromatic look that features a classic chore coat, simple black jeans, and a charcoal crewneck, with Middleton’s trademark demure jewelry. Middleton was wearing multiple thin rings long before Instagram influencers went wild over them.
38. Meghan Gets Physical
In this 2014 snap, Markle is getting physical for a celebrity sport competition, where she left with way more than a workout. While playing flag football for the event, Markle met her close friend, the tennis superstar Serena Williams. In the years to come, Williams would attend Markle’s royal wedding and throw her bestie an extravagant baby shower.
37. Diana Supports Her Sister
Picturing Diana at just 16 years old, this image shows the future princess acting as her older sister Jane’s elegant bridesmaid. In 1978, Jane Spencer married Robert Fellowes, the assistant private secretary to the queen. As of 2020, Spencer and Fellowes are still happily together. Sadly, not all the Spencer girls enjoyed such stable marriages.
36. Kate Shops Til She Drops
Kate is known for wearing more accessible clothing than most royals, rocking $10 earrings and Zara trousers. But on this occasion, she wasn’t looking for a bargain. In this 2009 photo, Middleton is shopping on London’s luxurious Bond Street and preparing to drop some major coin. Her outfit is business-casual, but her elegant Prada bag cements her high roller status.
35. Diana Gets Behind The Wheel
Diana was beloved for being the “People’s Princess” and this picture is a perfect example of why. In this 1980 image, Diana gasps as she accidentally stalls her new car, a fashionable Mini Metro. At the time, the vehicle must have been a real splurge. Diana was still working as a teacher’s assistant in the Pimlico neighborhood of London.
34. Meghan Mixes Things Up
You know you’ve made it when you get invited to a high-powered fashion brand’s party. By 2015, Markle was a major star and she was enjoying the limelight in this cheeky, pattern-mixing ensemble at a party thrown by Prada in New York City. Not everyone can pull off stripes and checks, but because Markle wisely keeps her patterns in the same color scheme and accessorizes with neutral tones, the outfit is a success.
33. The Kate Escape
In this 2007 snap, Kate is ready to get out of town. As she trots down the London sidewalk outside her home, the brunette beauty has keys in one hand and a duffle bag in another. As always, she combines classic outfit staples—crisp white shirt, fitted jeans, chic boots—with trendy items of the time. Even Kate Middleton couldn’t resist the siren song of Uggs in the 2000s!
32. Diana’s First Birthday
Diana didn’t have an especially easy childhood, as her upset expression in this photo might suggest. Her parents had a rocky relationship, she failed her school exams twice, and then dropped out at just 16 years old. Here she is at only one year old, unaware of the extraordinary life she will lead.
31. Kate-iana Jones
Kate’s a bit of a fashion chameleon. She usually opts for preppy, polished ensembles, but in this outfit, she pairs low-key jeans with a wide-brim leather hat and an earthy turquoise necklace. Even though she was attending an English horse racing event, Kate seems to have been inspired by American cowboys rather than British equestrians.
30. Meghan Makes A Famous Friend
Back in 2006, Meghan Markle’s first husband, the producer Trevor Engelson, worked on a comedy movie called License to Wed. It starred Robin Williams, John Krasinski, and a little someone named Mandy Moore. Over the course of filming, Markle and Moore became good friends and even celebrated New Year’s together. In this throwback snap, a young Meghan looks relaxed and trendy in a simple white dress.
29. Diana Runs In Aristocratic Circles
In this sweet 1981 snap, Princess Diana visits the swanky Broadlands estate owned by Lord and Lady Romsey. By this time, Prince Charles was officially courting Diana and everyone wondered when he’d pop the question. But few people knew that before Diana and Charles got together, he had a fling with Diana’s sister, Sarah. She’s actually the one who introduced them!
28. Kate Visits a Royal Castle
In 2004, Kate Middleton hammed it up for paparazzi at Blenheim Palace, where she attended Game Fair. However, she’s a lot more reluctant to pose for photos these days. It took until 2016 for Kate to pose for a magazine photoshoot—and she held out for the cream of the crop, only agreeing to shoot a 10-page spread for Vogue.
27. Baby Diana Defines Adorable
At two years old, Diana is the picture of a precious English baby. With her chubby cheeks, flaxen hair, and adorable Mary Janes, this image shows Diana taking adorable to the next level. She definitely looks like she belongs in a fairy tale story that sees a regular little girl become a royal princess.
26. Meghan Enters The Fashion Elite
Meghan is serving an adorable look in this snap taken at a screening hosted by the high fashion brand Miu Miu. Ever the fashionista, Markle pushes the button by unexpectedly layering a fluffy white coat over an otherwise casual outfit. She counter-balances the coat’s volume with a neat braid, pointed toe heels, and a fitted skirt.
25. Diana Eyes Her Beau
Diana and Prince Charles were engaged after a year of romance, but in all that time, they only went on a dozen dates. During their engagement period, however, Diana was often seen with her fiancé. Take this picture for an example: In the 1981 snap, a fresh-faced Diana is laser-focused on watching her beau Prince Charles play an energetic game of polo.
24. Kate Cheers On Prince William
This picture made the British public think twice about Kate Middleton. At first, it seemed like she was just a college girlfriend, but after she attended Prince William’s graduation from the Royal Military Academy Sandhurst, the press started to see that the couple was getting pretty serious. Kate attended the event with her parents and wore a stunning red coat to cheer on her man.
23. Diana Serves A Marty McFly Look
In the autumn of 1980, Diana was going on dates with Prince Charles, but they hadn’t made anything serious just yet. And…maybe this outfit is part of the reason for the delay. Channeling an English rose and wearing high heels, a frilly blouse, and a patterned skirt makes sense. Throwing a puffer vest over top? Not so much.
22. Kate Takes Chic To The Next Level
Carmen Sandiego, but make it fashion. This polished look took Kate through the 2008 Cheltenham Horse Racing Festival. While mixing navy and black doesn’t always work, Kate’s outfit sidesteps any fashion misses. Her pearl earrings, cozy black scarf, impeccably fitted trench coat, and slinky boots kept her warm and stylish throughout the horse races.
21. Diana Gets Her Hands Dirty
This throwback photo sees 10-year-old Diana on a family getaway to Itchenor in West Sussex. In 1971, she was a barefooted little girl getting ready to swing a croquet mallet. In the same year, her future husband Prince Charles would have been 22 years old. Yup, not enough people realize that there was over a decade’s age difference between the spouses.
20. Pippa Enters The Ring
In 2007, Kate and Will encountered some turbulence. At the time, Will was stationed outside London, while Kate was struggling with the media frenzy over their relationship. At a certain point, the couple couldn’t handle the distance and the pressure and they decided to break up, leaving Kate free to mingle on the town. Here she is at a book launch with her sister Pippa, flaunting her incredible figure in this slinky pearl-hued dress.
19. Meghan Explores Fringe Science
Before Meghan’s big break on Suits, she landed a role on the second season of the sci-fi thriller Fringe, starring Joshua Jackson and Anna Torv. Even though Markle’s character, an FBI agent named Amy, was clever and sexy, she only appeared in two episodes. After that, Markle headed back to the audition circuit. Fringe‘s loss!
18. Diana Sets The Stage For Kate’s Iconic Red Coats
The royal family loves a good statement coat and this red velvet blazer is no exception. While Diana would one day become a fashion icon for her daring dresses and formalwear, this casual outfit proves that she already had style back in 1980. With her pinstripe skirt, soft black turtleneck, and bold gold earrings, Diana makes the 80s look good.
17. Kate Becomes a Style Icon
Back in 2007, Kate turned 25 and received a very nice present: She was dubbed a style icon by the British people. When paparazzi released shots of Middleton wearing this vintage-inspired black and white dress, fashionistas hunted down the garment and realized it was an affordably priced tunic from Topshop. The dress immediately sold out, cementing Kate’s street style savvy.
16. Diana Puts Family First
In 1968, Diana and her little brother Charles bravely toddled out of the Spencer family home and posed for a picture. The kiddos are smiling, but looking back, Diana described this as a very unhappy time for her family. The Spencer parents had already broken up by the time of this snap, and things would only get worse as their divorce became a bitter feud.
15. Kate Combines Brains and Beauty
Before she was a jet-setting duchess and mother of three, Kate Middleton was a beautiful young woman pursuing a degree in Art History at St. Andrews University. Kate couldn’t have known it when she applied, but going to St. Andrews would change her entire life. After all, it’s where she famously met Prince William. Here she is in 2005 on graduation day.
14. Meghan Gets Her Glow On
This throwback shows a young Meghan Markle a year before Suits premiered and made her a star. As Markle attends a beauty and style event in 2010, she coordinates her thin grey belt with streamlined flat sandals. The neutral accessories let her fun pink dress take center stage…and possibly disguise passersby as Meghan grabs every swag bag in the room.
13. Diana Rocks Some Overalls
Can’t you picture this outfit on a vintage-inspired fashion blogger’s instagram? The pastel yellow overalls, sweet Peter Pan collar, and understated gold jewelry would translate surprisingly well to 2020. In this snap from a polo match in 1981, Diana’s already impressing the public with her knack for unexpected yet attractive outfits.
12. Kate Works the 00s
Shortly before Kate graduated from the prestigious St. Andrews University in bonny Scotland, she was snapped exiting a convenience store with her dear old dad. Like any other college girl, Middleton is clad in a simple 2000s outfit—boot cut jeans, white camisole with lace trim, and minimal jewelry—but the future duchess still manages to look effortlessly perfect.
11. Little Diana Rides In Style
This image shows infant Diana riding in style through the grounds of Park House, where she was born in Norfolk. With her ornate carriage, it seems like Diana was always destined to become a princess, and in a way she was born into royalty. After all, her grandmothers were ladies-in-waiting to Queen Elizabeth, The Queen Mother.
10. Kate Has A Rough Night
In her mid-twenties, Kate Middleton knew how to have a good time. Here she is exiting a raucous 2007 Halloween party at London’s exclusive Mahiki Club. Like a normal girl enjoying her youth, Kate partied the night away in a risqué costume. With her sparkly dress, satin cape, fishnet stockings, and fun, bright pink bag, she transforms from college student to hot witch in charge.
9. Meghan Prepares For Fame
In this 2006 photo, a young, fresh-faced Meghan attends the ALMA awards and rocks some mid-oos fashion staples: faded boot cut jeans, wedge heels, and a long statement necklace. At this time, Markle would have been dating her longtime boyfriend, film producer Trevor Engelson, but by 2013, they’d be divorced.
8. Diana Goes All Out
What screams “British royal family” more than top hats and horse racing? The Windsors traditionally attend the Royal Ascot, so when Diana joined them in 1981, it was a signal to the world that she was a genuine new member of the royal family. Her, um, candy cane-inspired outfit, however, did not make the greatest impression—but hey, it was the 80s.
7. Kate Schools Us With A Preppy Look
It seems like Kate was tailor-made to join the British royal family. In this classic, J. Crew-inspired look, Middleton effortlessly glides through the Badminton Horse Trials, a staple in the well-to-do-Brit’s event calendar. Even though the picture was taken back in 2007, Kate’s navy blue cable-knit sweater, brown leather belt, and snug white skirt could all easily be worn today.
6. Meghan Grabs A Swag Bag
Baby Meghan loved a swag bag. Here she is at a pre-Emmy awards gift lounge in 2009, stocking up on all the goodies that Hollywood has to offer. With her chic all black ensemble, aviator sunglasses, and fashionable handbag, Meghan is on her way to the big time. In just a few years, she’d finally become a major TV star.
5. Diana Keeps Things Prim
In the time just before Diana and Prince Charles wed, the royal couple attended multiple events together, like this 1981 appearance in Tetbury. Even though Diana acquiescently joined in on publicity tours with Charles, she wasn’t 100% docile. In her vows, she intentionally left out the bit where she swears to “obey” her husband. You go, Diana.
4. Kate Works a Beret
Kate showed off her natural beauty in this chic look, worn at a horse racing festival in Cheltenham. With a very 2000s color combo of baby blue and chocolate brown, Kate coordinated her elegant beret with chandelier earrings, a patterned scarf, and knee-high boots. With outfits like this, Kate was primed to take over Princess Diana’s status as a fashion icon.
3. Meghan’s Star Rises
By 2013, Meghan’s show Suits was a major hit and she was finally enjoying life as a well-regarded actress. All her years of hard work finally paid off, as she got to attend swanky events like Entertainment Weekly’s Pre-Screen Actors’ Guild Awards party. With her gold accessories and effortless, multicolor gown, Meghan Markle has officially arrived.
2. Kate Makes Will Regret Their Breakup
This is how you make a man regret that he let you go: When Kate and Will called it quits in 2007, Middleton didn’t lie in bed eating chocolates and watching romantic comedies. Instead, like the fierce athlete she is, she channeled her energy into sports. Middleton joined an all-girl rowing team who trained to cross the English Channel.
1. Diana Savors Her Last Month of Freedom
Despite her bright cherry red ensemble, Diana doesn’t look particularly happy in this picture, which was taken just a month before her extravagant wedding to Prince Charles. Diana’s instincts were onto something. Her “fairy tale wedding” would turn into a deeply unhappy marriage. After both Charles and Diana began to secretly see other people, the queen herself demanded that they split.