Kate Middleton's Chic Wimbledon Outfits Over The Years, Ranked

While it would be unfair to reduce Kate Middleton to being the kind of fashionista who chases every fleeting fad, typically, she's ahead of the game when it comes to style. Of course, Middleton has experienced some fashion mishaps that left royal fans stunned, but more often than not, her public appearances prove that she's got a knack for having the perfect balance of trendy and timeless. Nowhere is this more evident than through her yearly Wimbledon appearances, where each of her outfits always seem to be the perfect combination of traditional yet current. 

With it being well over a decade since the Princess of Wales has attended the games as of 2025, it's the perfect opportunity to take a closer look at some of her most iconic Wimbledon outfit moments over the years. The focus is on her looks from 2016 through 2025, a period recent enough to reflect evolving trends while highlighting her sartorial growth. Some years, she donned multiple standout ensembles, so don't mind outfits from the same year as we felt compelled to give each fabulous look the recognition it deserves. 

The outfits have been ranked to highlight which outfits made the biggest impact to royal family fans and fashion aficionados alike. From a stunning Self-Portrait lime green dress to a one-of-a-kind mint green Balmain blazer, each ensemble showcases the Duchess's and her styling team's attention to detail, working with both bold and neutral colors to create looks that feel modern but also classic. 

Though we applaud the princess for going for understated elegance, a skirt-and-tee combination leaned a little too business casual for a summer sporting occasion. The royal styled her closet staple with a navy polka-dotted midi skirt by Alessandra Rich, navy blazer, accessorizing with a drop pendant necklace and pearl earrings for understated elegance. Though the look may have worked for a luncheon, it was a let down for such a high profile event. The choice to style the look with white heels and bag made it seem like she was headed to a chic office meeting. 

While the Jenny Packham dress Kate Middleton wore to Wimbledon in 2018 isn't one of our favorites, it was one of the most fitting for the occasion. The fitted cream midi dress by the British designer (who is most famous for her iconic wedding gowns) was covered in a round pattern that strongly resembles tennis balls. And what better place to wear a dress like this then to Wimbledon? Don't get us wrong, the playful print dress and the Dolce & Gabbana top handle bag went perfectly well together and were delightfully on-theme, but overall, felt a bit too simple and lacked the elevated polish she's become known for. 

Don't get us wrong, Kate Middleton looks absolutely stunning in this custom forest green Dolce & Gabbana midi dress. The fitted silhouette, puff sleeves, and gold button detailing and the vibrant color, this dress was practically made for someone like her. Paired with nude pumps and a Dolce & Gabbana top handle bag, the ensemble was pure elegance. That said, the structured fabric probably made sitting through a full tennis match quite the challenge. So, while the overall look was perfection, we didn't find it fitting for the occasion. 

The cobalt blue dress by Roksanda Kate Middleton donned for Wimbledon 2025 was a refreshing color choice perfect for summer, but not her most refined moment. While the dress was fun and the voluminous skirt offered plenty of movement, the overall styling felt a bit discombobulated. The huge bow detail wasn't our favorite. On top of that, the addition of wide-brimmed straw hat and almost brown pumps made the outfit feel more garden party chic vibe. The color and silhouette were very flattering on the princess, but there was a lack of cohesiveness and polish in comparison to her stronger Wimbledon looks. 

The beautiful purple midi dress Kate Middleton wore to Wimbledon 2024 gave another London-based brand, Safiyaa, the attention it deserved. On top of that, the gown itself was the epitome of colorful elegance. Its twisted and pleated detailing made the skirt flow, giving it a true princess-like quality. The tan heels and the gold accessories added a touch of warmth and polish to the look. The overall fit and detailing of made the dress feel much more refined and flattering than the cobalt Roksanda dress she wore to 2025 Wimbledon. 

In 2022, Kate Middleton showed up to the Men's Final Match in a very casual polka-dot printed dress for summer by London-based designer Alessandra Rich. The timeless print, which the mother of three has been spotted wearing numerous times, proved once again she knows just how well it works for her. Meanwhile, the slightly structured shoulders, ruffle detailing, and A-line silhouette emphasized her long and lean figure. Finally, the two-tone heels added a fun and nostalgic touch to the ensemble. While many avoid polka dots as they can feel dated, the princess easily mades them modern and flattering. 

For the Men's Final during the 2016 Wimbledon games, Kate Middleton showed up in a Alexander McQueen dress that marked a playful departure from her usual Wimbledon style. The garment features a pattern of eclectic skulls and petals, which added a cheeky and rebellious edge rarely seen in royal attire. With the beautiful print of the dress taking center stage, the royal kept her accessories quite simple, pairing the look with statement gold earrings and her favorite go-to timepiece, the Cartier Ballon Bleu watch. 

Kate Middleton must have loved the lime green Self-Portrait dress from Wimbledon 2023 as much as we did, because she pulled a chic case of pleated déjà vu for the 2025 Wimbledon games. This time, she went with the white version of the same collared midi dress, proving there's no reason not to give an encore to a piece that works for you. While the lime green version was our absolute favorite, the ivory iteration felt just as elegant and fresh. Paired with neutral suede pumps and the perfect summer tote by Anya Hindmarch, the look was simply Wimbledon perfection.

The 2023 Wimbledon games was an iconic year for Kate Middleton, style-wise. Her mint green Balmain blazer wasn't just the only showstopper of the year. On the final match day, she turned heads in a lime green Self-Portrait Boucle Collared Chiffon Midi Dress. The vibrant hue was perfect for the summer, while flowing, pleated skirt brought energy and movement to the look. It was the perfect balance of elegance and playfulness.

This mint green Balmain blazer and white pleated skirt moment in 2023 doesn't just take the top spot on this Wimbledon list — it may very well be one of Kate Middleton's best looks of all time. The structured double-breasted blazer looks absolutely stunning on her slender figure and the stunning mint and white color combination complemented her complexion beautifully. The stylish addition of the white Gianvito Rossi pumps and white Mulberry mini bag perfect this look. It was so classy and timeless while also refreshingly on-trend for the time. It seemed to be a nod to Princess Diana, her late mother-in-law would surely approve. 

Everyone knows Kate Middleton has an enviable wardrobe that draws out so much fall fashion inspo for those who like to dress with class and elegance. You can only imagine how difficult it was for us to ranking our favorite chic Wimbledon looks from the past several years. While the process was largely subjective, there were a few key factors that guided our decisions. First and foremost, the overall impact of an outfit was key. How memorable was the look? How well did it photograph? Other factors we considered were whether the ensemble was appropriate for the occasion, as well as the degree to which it successfully balanced sophistication with approachability.

While it's a must that the Princess of Wales looks good in every outfit she makes a public appearance in, the appropriateness to the occasion also matters. Wimbledon is a unique event, one in which three's a mix of formality, tradition, and outdoor practicality. So, whether it be a midi dress or fitted blazer, the ensemble needs to look polished while also allowing ease of moment in the outdoors. Some other factors that were also considered were fit, silhouette, and print. These are crucial elements that can take a look to a whole other level. For instance, the belted Self-Portrait dresses scored high on the list because their pleated skirts and cinched waist detailing perfectly flattered Kate's figure while allowing effortless movement.