Rare Pics of Diana, Kate & Meghan Before They Were Royals

44. Diana Meeting Grace Kelly – 1981

In 1981, Lady Diana Spencer met Grace Kelly for the first time at an event in London’s Goldsmith Hall. This was her first public engagement as Prince Charles’ fiancé. Princess Grace reportedly gave Diana some advice that evening about entering the British royal family: “Don’t worry dear – it’ll only get worse.”

43. Kate at the Bluebird Store Opening – 2006

Kate attended a launch party in 2006 for the opening of the King’s road shop, Bluebird. She dressed to impress in this colorful dress, which featured pink, purple, blue and yellow flowers with a light pink blazer, a dark pink purse and purple shoes.

42. Meghan at the Summer TCA Party – 2011

In 2011, Markle attended the Summer 2011 TCA Party with the cast of Suits, which must have been a pretty big deal for her. Prior to this, Markle hadn’t had any big breaks. This was a first for her.

41. Kate at the Wedding of Camilla Parker Bowles’ Daughter – 2006

In 2006, Kate attended Camilla Parker-Bowles’ daughter Laura’s wedding to former underwear model Harry Lopes with Prince William. This was a really big step in their relationship and meant that Kate was completely accepted in royal circles.

40. Diana at the Young England School – 1980

Before marrying Prince Charles, Diana had a job at the Young England School in Pimlico as a teacher’s assistant. This was a pretty big deal. She was reportedly the first woman in British history to have held a paying job before marrying the heir to the throne.

39. Kate at the Day-Glo Midnight Roller Disco – 2009

Middleton attended the Day-Glo Midnight Roller Disco, a fundraising event in aid of the Children’s Hospital in Oxford, back in 2009. She organized the event in memory of her friend Thomas Waley-Cohen, who died from bone cancer in 2004 when he was just 20 years old.

38. Meghan Out and About for Celebrity Candids – 2015

Meghan was out and about in New York City for Celebrity Candids in this photo. She was such a natural. How many other people can dress to the nines like this, pose for photographs and look completely comfortable?

37. Diana at Cadogan Place Gardens – 1968

During the summer of 1968, Diana visited Cadogan Place Gardens in London. This photo appears to have to be taken on what would have been her seventh birthday. She looks absolutely precious in this little red dress with a matching headband and a blue cardigan. Even as a child, she had style.

36. Diana at a Fundraising Concert at Goldsmiths Hall – 1981

All eyes were on Princess Diana during her first public appearance at a fundraising concert at Goldsmiths Hall in London in 1981. In this photo, one can see the sea of photographers in front of her as she stands there in a beautiful black taffeta dress. It was just the beginning of what would be a very crazy life in the spotlight.

35. Kate Out and About in London – 2007

A day before her 25th birthday, Middleton was out and about in London in a brown coat, a dark pair of jeans and a perfect blowout. She must have been doing some dry cleaning, hence the red wool coat she’s carrying around.

34. Meghan at DirecTV’s 8th Annual Celebrity Beach Bowl – 2014

In 2014, Markle participated in DirecTV’s 8th Annual Celebrity Beach Bowl. This is where she met one of her closest friends, Serena Williams. On The Tig, Markle wrote, “We hit it off immediately, taking pictures, laughing through the flag football game we were both playing in, and chatting not about tennis or acting, but about all the good old fashioned girly stuff. So began our friendship.”

33. Diana as a Bridesmaid at Her Sister Lady Jane’s Wedding – 1978

In 1978, a young Diana was a bridesmaid at her sister Lady Jane’s wedding to Robert Fellowes. She was just 16 years old in this picture. While Diana’s marriage to Prince Charles ended in divorce, her sister’s marriage is still going strong more than 40 years later.

32. Diana Stalling Her Car – 1980

In 1980, the beautiful young aristocrat couldn’t escape the press. Here she is in her new car, a Mini Metro, outside the school in Pimlico where she worked as a teacher’s assistant. She stalled her car and had quite the expression on her face.

31. Meghan at Prada’s The Iconoclasts Event – 2015

Markle attended Prada’s The Iconoclast Party in New York City in 2015. The actress was decked out in this Prada ensemble. Although the patterns that she was wearing clashed, Markle made the whole thing look chic.

30. Diana on her First Birthday – 1962

Princess Diana was just a year old in this picture. While she had said that her childhood was incredibly unhappy, there’s no denying that her family was quite privileged. Her father, Earl John Spencer, was a wealthy landowner and his family had been closely linked with the royal family for several generations.

29. Kate at the Festival of British Eventing – 2005

After graduating from the University of St. Andrews in 2005, Middleton attended the Gatcombe Park Festival of British Eventing at Gatcombe Park with her mother, Carole. She looked super casual in this brown jacket, turquoise sweater, brown hat and blue jeans.

28. Meghan at The Pink Elephant Night Club – 2006

Who knew that Mandy Moore and Markle were friends? Here they are back in 2006 at The Pink Elephant Night Club in Southampton. The two met through Trevor Engelson, Markle’s first husband. He was directing a film Moore was in called License to Wed, so she and the future Duchess became friends.

27. Diana at Broadlands – 1981

Before she was married to Prince Charles, the bride-to-be visited Lord and Lady Romsey at their country estate, Broadlands, in May 1981. She looked so fresh-faced in this picture in this green ensemble.

26. Diana as an Infant – 1963

At the age of two, Lady Diana looked a bit like a doll. She had this beautiful porcelain skin with this beautiful blonde hair. She also dressed in the cutest way. How precious is this little dress with these buckle shoes?

25. Meghan at Miu Miu Women’s Tales 7th Edition – 2014

The Suits star was at Miu Miu Women’s Tales 7th Edition. She attended the screening for the short film Spark and Light, which starred Riley Keough. Markle looked super stylish in this outfit by Miu Miu. She was probably styled by her bestie, Jessica Mulroney.

24. Diana Watching Prince Charles Play Polo – 1981

Prior to her wedding with Prince Charles, Lady Diana was already spending time at various polo matches watching her soon-to-be husband play. She looks so young and innocent in this picture – like she no idea how crazy her life was about to become.

23. Kate at Prince William’s Military Academy Graduation – 2006

When Prince William graduated from the Royal Military Academy Sandhurst, his girlfriend was there with her parents watching. She showed up in a red wool coat and a large black hat. The fact that she was there was a big deal and had some speculating that the two might be getting engaged.

22. Diana at Her Flat in London – 1980

Here is Princess Diana in September 1980. At this point, Prince Charles had already begun courting the 19-year-old aristocrat. This is a photo in Diana’s flat. She was clearly still figuring out her style. The big, puffy vest just didn’t go with the blouse and floral skirt.

21. Kate at the Cheltenham Horse Racing Festival – 2008

The British beauty attended The Cheltenham Horse Racing Festival in 2008 in style. Here she is looking stunning in a navy trench with black tights, black boots, a black purse, a black scarf, and a black fedora.

20. Diana on Holiday in Itchenor, West Sussex – 1971

Back in the summer of 1971, Diana went on a vacation in Itchenor, West Sussex. Here she is barefoot with a croquet mallet. Although she was never that inclined academically, she was reportedly really good at sports, including swimming and diving, and was skilled at ballet and tap dance.

19. Kate at the Young Stalin Book Launch – 2007

While on a break from Prince William in 2007, Kate Middleton hit the town with her sister Pippa and attended the Young Stalin book launch in London. She was definitely showing William what he was missing with this lacy dress!

18. Meghan on the Set of Fringe – 2008

Meghan joined the cast of Fringe during season two. She played FBI agent Amy Jessup, an attractive, brash and quick-witted junior agent. She was only on the show for two episodes before she completely disappeared without a trace.

17. Diana in London – 1980

This picture is from 1980 when Lady Diana was first romantically linked to Prince Charles. She’s in London near her flat as she is being trailed by photographers. She already knew a thing or two about fashion with her red blazer and pin-striped skirt.

16. Kate on Her 25th Birthday – 2007

On Kate’s 25th birthday, she stepped out wearing this black and white retro tunic dress from Topshop that retailed for about $78. After this photo surfaced, the dress completely sold out, proving that the royal girlfriend was quite the fashion icon.

15. Diana with her Younger Brother Charles – 1968

Princess Diana was closest in age with her younger brother, Charles, who was about three years younger than she was. Here the two of them are in 1968. Although it is hard to tell by the smile on Charles’ face, this was a rather unhappy time. Their parents had separated a year earlier and were going through an acrimonious divorce.

14. Kate at Her University Graduation – 2005

This picture is from June 2005 when the pretty brunette graduated from St. Andrews University with a degree in the history of art. As most people know, she met Prince William while she was studying in Scotland. They lived in the same residence, St. Salvatore’s Hall.

13. Meghan at the Some Kind-a Gorgeous Style and Beauty Lounge – 2010

This photo is from 2010 at the Some Kind-a Gorgeous Style and Beauty Lounge. Even though Suits wasn’t yet on the air, Megan had already been cast on the show at this point. It would be almost a year later that the show would finally debut on USA Network and make Meghan a star!

12. Diana at Polo Match at Windsor Great Park – 1981

Lady Diana attended a polo match at Windsor Great Park in July 1981 wearing a yellow pair of overalls. It’s a good look for the princess-to-be. She looks young, sweet and innocent, which is exactly what she was!

11. Kate in St. Andrews, Scotland – 2005

This picture was taken shortly before Middleton graduated from St. Andrews University. Kate was out and about in St. Andrews with her father and was dressed really casually. Her cami top and low cut jeans are so 2005!

10. Diana at Park House, Sandringham – 1963

Princess Diana was born in Park House, Sandringham, Norfolk, and that’s where she spent a good part of her childhood. Here she is as a young child on the grounds of Park House in her pram. She looks absolutely precious!

9. Meghan at the ALMA Awards Gifting & Lifestyle Suite – 2006

Meghan was just a struggling actress when this photo was taken. She was at the ALMA Awards Gifting & Lifestyle, posing for some photos and looking at some merchandise in 2006.

8. Diana at the Royal Ascot – 1981

The Royal Ascot is a tradition for the royal family. Princess Diana rocked a Bellville Sassoon outfit at her first appearance at the Royal Ascot in June 1981. It was definitely not her finest fashion moment ever, but it only got better from here!

7. Kate at the Badminton Horse Trials – 2007

Prior to becoming a royal, the British commoner’s style was very preppy. Here she is at the Badminton Horse Trials in 2007 looking like she just stepped out of a Ralph Lauren catalog. The white jean skirt paired with the blue sweater and blouse is so preppy but still stylish.

6. Meghan at the DPA Pre-Emmy Gift Lounge – 2009

When Markle was just a struggling actress who wasn’t getting many roles in Hollywood, she was attending small events – like this one! Here she is at the DPA pre-Emmy Gift Lounge at the Peninsula Hotel in Beverly Hills picking up some swag.

5. Diana in Tetbury – 1981

Here Diana is before her wedding to Prince Charles in 1981. She wasn’t really taking any risks with her fashion back then and was dressed quite conservatively. During an appearance with Prince Charles in Tetbury, she wore an ivory blouse with a red polka dot blazer and red skirt.

4. Kate at the Cheltenham Horse Racing Festival – 2007

The gorgeous brunette attended the Cheltenham Horse Racing Festival in style in March 2007. She rocked this asymmetrical brown skirt with a pair of brown boots, a baby blue coat with brown detailing, and a brown beret. She topped the look off with a pashmina scarf.

3. Meghan at the Entertainment Weekly Pre-SAG Party – 2013

In 2013, the former television actress attended the Entertainment Weekly Pre-SAG Party, which was hosted by Essie and Audi and held at Chateau Marmont. The rising star looked super gorgeous in this multi-colored gown.

2. Kate Training with the Sisterhood – 2007

After her breakup with William in 2007, beautiful Kate didn’t waste her time wallowing. Instead, she joined the sisterhood, a group of female athletes who were training to become the first all women crew to cross the Channel in a traditional Chinese dragon boat.

1. Diana at Nicholas Soames’ Wedding – 1981

This photo is from June 1981 – a month before Diana married into the royal family. She was with Princess Margaret, the Queen Mother and Prince Charles leaving Nicholas Soames’ wedding. We love her red dress and matching hat!