The Worst-Dressed Wimbledon 2025 Attendees

For tennis fans, one of the biggest events of the year has arrived. Wimbledon 2025 is in full swing — no pun intended — taking place from June 30 to July 13. The athletes are playing their hearts out and the celebs are loving what they are watching from the stands. Of course, there is plenty to watch on the court, but at a star-studded event like this, sometimes it's even more fun to direct your attention to the sidelines as an unexpected fashion show awaits.

As we've come to expect when stars are dressing to the nines, some served looks, while others hit the metaphorical net. Many stars arrived in their summery Sunday best to watch the matches, but other celebs' outfits were anything but hits. While the officials are the ones overseeing the matches themselves, consider us the ones making calls about what's going on off the court. We've got all the Wimbledon 2025 attendees' looks that were just plain flops.

That little house-shaped bag Dawn O'Porter was carrying? Adorable! The rest of the outfit she paired it with? Not so much! This dress just didn't suit O'Porter at all. Not only was the overall print and color palette unpleasing to the eye, but the fit overwhelmed her. It was noticeably baggy, and the hem hit her at a strange spot mid-calf, which made her look like she was swimming in it. Plus, pairing it with granny shoes only took this look from bad to worse.

Apparently dressing wacky for Wimbledon was a family affair for Dawn O'Porter and her hubby, Chris O'Dowd. At first glance, it appeared that O'Dowd forgot his pants when heading to the famous tennis tournament. However, on second thought, this shorts, blazer, and boots with high socks combination must have been some sort of SpongeBob SquarePants cosplay. In any event, every single element of this ensemble clashed with the others, and while this is an impressively difficult feat to achieve, it definitely doesn't make for a good look.

Sure, Miquita Oliver's outfit looked comfy, but at what cost? Nothing about this 'fit was coordinated. The seafoam green, low-rise cropped pants may have worked for some kind of beach day, but why did she pair it with these clunky black shoes and shiny, copper shoulder bag? It's hard to come up with any reasonable explanation for this 'fit other than the idea that Oliver simply grabbed a few random items for her closet one minute before heading out the door.

This blue-and-white striped matching set definitely isn't among the most inappropriate outfits Princess Beatrice has ever worn, but it wasn't one of her best looks, either. The thin blue and white stripes paired with white floral appliqués certainly felt summery. Yet, the oddly voluminous sleeves threw off her silhouette. Furthermore, while a hat could have added something to this look, a fedora with green detailing didn't make any sense with the rest of the ensemble.

Wearing a brown shirt with brown pants is a downright odd fashion impulse. And it's this exact misguided outfit formula that just made Jeff Bezos one of the worst-dressed people at his own wedding weekend. While this is a trend we can't possibly understand, it does seem like it may be gaining traction, now that Gregg Sulkin wore a similar look to Wimbledon. Not only is this whole outfit boring brown, but the shirt, pants, and shoes are all different shades, achieving the rare fashion blunder: monochromatic, yet still somehow clashing.

The top half of this outfit looks chic and put-together, so why does the bottom half of the outfit appear borrowed from a grandma running errands in the summer of 2002? The capri pant? The white thong sandals? The out of place black shoulder bag? Sure, Y2K style may be on-trend at the moment, but Rochelle Humes proved that not every early aughts look is primed for a comeback — or, at least we hope they're not. 

Wide-leg pants are definitely having a moment, but Tom Daley's baggy suit pants are clear evidence that this trend needs to be done the right way to really work. The pants' length and volume paired with their high waist, his long tie, and the clown shoe-esque footwear made for an outfit that felt silly and cartoonish rather than unique and modern. The sage green color would have been an interesting pick for the occasion, but it would've looked better in the form of a sleeker, more fitted suit.

Jade Holland Cooper seemed to channel her inner Beetlejuice in a bold pinstripe jacket while watching Wimbledon. She made more than a few odd choices when styling this jacket, pairing it with many other patterns, including a subtly polka dot tie, a striped button-down, and white pinstripe pants. She also added a heavy gold tie bar and some circular gold sunglasses. All these statement-making elements put together with a slicked-back hairstyle made Cooper look like the bad guy in a classic cartoon.

Molly-Mae Hague got her Wimbledon outfit all wrong with a simple khaki dress. For starters, this color blended in and washed her out — but the worst part of the look was the fit. The skirt was voluminous and went to her ankles, which distorted her proportions and made her look particularly short. The bunching of the fabric around the belt made the dress appear too big for her frame, and the wide sleeves had the same effect. Overall, she looked like she'd been swallowed up by this dress.