Princess Charlotte is entering her tween era in the most stylish way.

When the 9-year-old royal stepped out with her mom, Kate Middleton, and aunt Pippa Middleton at the men’s finals at Wimbledon on July 14, she wore a polka dot dress that was reminiscent of a dress her mom sported at the same event two years earlier, styled with pink Ray-Ban sunglasses and a touch of lip gloss.

Bethan Holt, Style Director at the Daily Telegraph tells PEOPLE, “It felt like a bit of a milestone, like she’s transitioning from a sweet little girl in smocked floral dresses to a slightly more grown-up tween vibe.”

The chic dress from American brand Guess was accessorized with more youthful accessories: handmade friendship bracelets, her hair braided and tied with a navy bow and white ballet pumps, the Missi style from one of the family’s favorite footwear brands, Papouelli.

Kate Middleton; Princess Charlotte.
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“She looked lovely, and we are always thrilled when she wears our shoes,” co-founder of Papouelli Nicole Robinson tells PEOPLE, adding that she has been dressing the feet of all the Wales’ children for several years.

“She has transitioned from a very gorgeous Mary Jane shoe into a ballerina style which is very age-appropriate,” Robinson says.

The Missi, which retails from $125 and comes in several colors, is one of the brand’s most popular styles for a reason.

“That style has been in our collection for about 15 years, and all the little girls love them because they are so incredibly comfortable,” Robinson explains. “The sole is so lovely and soft.”

Kate Middleton and Princess Charlotte at Wimbledon on July 14, 2024.
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While casual moments (such as a recent candid photo of Prince William with Charlotte and her two brothers, Prince George and Prince Louis, leaping over the sand dunes that was released to mark the Prince of Wales’ 42nd birthday) still show the young princess in everyday attire like playsuits and Breton jumpers, it’s the formal occasions where Charlotte’s new look is starting to emerge.

At the Coronation Concert in May 2023, Princess Charlotte was photographed singing along enthusiastically to Katy Perry while wearing an ivory dress from Self Portrait, a cool-girl British brand often worn by her mom and other royals such as Princess Eugenie and Princess Beatrice. With its layered tiered skirt and sheer puff sleeves with black bow detailing, it was more than a nod to a Self Portrait midi dress worn by Princess Kate in 2023.

Kate Middleton and Princess Charlotte both wearing Self Portrait.
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“I think Kate has a really elegant, effortless classic style, and she always looks amazing so you would assume that would filter down to what she chooses to dress her daughter in,” says Robinson, whose white Mary Jane shoes Charlotte also wore to the historic coronation ceremony at Westminster Abbey on May 6, 2023.

For that occasion, the royal mother and daughter duo were also coordinated in matching silver bullion and crystal flower crowns by Jess Collett and Alexander McQueen. It was also at the coronation of her grandfather King Charles, the most formal public engagement Charlotte has attended to date, that she wore (publicly, at least!) her first piece of bespoke Alexander McQueen couture.

Kate Middleton and Princess Charlotte at King Charles’ coronation in May 2023.
Karwai Tang/WireImage

With Princess Kate sticking to a well-tested formula when comes to her style, it’s no surprise to see the same emerging for Charlotte — for example, Trooping the Colour has had a nautical theme for the last two years!

“The Princess of Wales dresses Charlotte so beautifully. She always looks immaculately turned out, and I’m sure as she gets older that will continue to be the case,” says Robinson, adding of Kate’s styling choices, “She always gets it spot on.”