Joshua Goldman
Joshua Goldman
min read · July 11, 2025 · Entertainment

Wimbledon in Style: Hollywood Stars Make a Splash with Unique Fashion Choices!

Will Poulter (pictured) appeared to be wearing wonky trousers and odd socks

WIMBLEDON WILDCARD: Tinseltown's A-Listers Steal the Show at the Men's Semi-Finals!

The sun was shining bright, and so were Hollywood's hottest stars as they descended upon the hallowed grounds of Wimbledon! That's right, folks, we're talking about the crème de la crème of Tinseltown, including Will Poulter, Benedict Cumberbatch, Rami Malek, and even the incomparable Leonardo DiCaprio, who all gathered to witness the penultimate matches in the singles competition.

But let's get to the real story: Will Poulter's fashion faux pas! The actor's trouser legs appeared to be a mismatched pair, with one showing off his quirky socks. We're not sure what was more shocking – the uneven hem or the fact that he still managed to rock a white and light blue pinstripe summer suit with a white shirt, black tie, and smart black shoes! Talk about making it work!

Benedict Cumberbatch sported a moustache and navy suit as he held hands with his wife Sophie Hunter

As for the rest of the A-listers, Benedict Cumberbatch brought his signature suave to Wimbledon, sporting a navy suit and mustache as he held hands with his wife Sophie Hunter. Rami Malek opted for a light champagne-colored suit and matching diagonal striped tie – and looked like a million bucks doing it! James Norton kept it low-key in shades while chatting with pals.

But the real queen of the tournament was none other than Anna Wintour, who wowed in an elegant white buttoned-up dress adorned with blue flowers. Her signature dark shades added a touch of sophistication to her overall look. This marked the second time she's been spotted at Wimbledon since announcing she'll be stepping down as editor-in-chief after 37 years – talk about making an exit!

Other notable attendees included Riz Ahmed, Joe Alwyn, Jamie Laing and Sophie Habboo (looking radiant in a colorful floral mini dress), Louis Theroux, and Rob Beckett. Jessica Plumer stole the show with her off-the-shoulder cream statement top and coral red leather skirt – we're still trying to figure out how she pulled that look together!

Leonardo DiCaprio was also spotted in the crowd as he kept a serious expression during the game

As for the tennis action on Centre Court, defending champion Carlos Alcaraz is set to face American Taylor Fritz in a battle for a spot in the final. Later on, World No. 1 Jannik Sinner will take on seven-time winner Novak Djokovic – it's going to be a thrilling match!

But let's get back to the drama: Aryna Sabalenka, the world's top-ranked tennis player, lost to U.S. 13th seed Amanda Anisimova in Thursday's matches. When asked about her experience, Sabalenka admitted she has a "hate relationship" with Wimbledon –ouch! She hopes that one day she'll turn things around and have a love-hate relationship with the tournament.

TheScholarlyNote.com has got you covered for all the juiciest gossip and updates from Wimbledon. Stay tuned for more exciting developments, and don't forget to keep your eyes on those tennis courts – it's going to be a wild ride!

The Hollywood star opted for a simple grey blazer jacket and white T-shirt as he watched the Taylor Fritz and Carlos Alcaraz match

Sources: TheScholarlyNote.com

There seemed to be some serious swooning over Leonardo at he sat in the stands

Also in attendance was fellow Hollywood stars Riz Ahmed and Joe Alwyn as well as the UK's favourite podcasting couple Jamie Laing and Sophie Habboo (pictured)

James Norton was also seated in the Royal Box as he kept a low profile in shades

Anna was spotted chatted to James (right) and his father Hugh

He kept cool during the match with a branded Wimbledon fan

Benedict and his wife were seen chatting with Rami as they sat front row

Leonardo looked to be concentrating hard on the match

Will appeared to suffer a slight fashion faux par as his trouser legs appeared different lengths with one showing off his socks

Anna Wintour joined the men as she wowed in an elegant white buttoned up dress adorned with blue flowers

Rami kept it stylish as he opted for a light champagne coloured suit and matching diagonal striped tie

The star  posed with her husband Jamie who opted for a simple T-shirt and cream trousers combo

The star added black circular shades as he attended the All England Lawn Tennis and Croquet Club

The star - who is typically spotted wearing a baseball cap - went without his headgear

Hannah Waddingham was also seen enjoying the game from the crowds

Tennis legend Pat Cash was there with his partner Charlotte Hodson

The actor opted for a white and light blue pinstripe summer suit which he paired with a white shirt and black tie

Keeping it casual Joe opted for alight blue T-shirt, darker blue trousers, white trainers and shades

Anna posed alongside Tom Ford, in her second public appearance since the bombshell news she will be stepping down from one of her roles at Vogue after 37 years

The pair were seen settling down beside each other in the Royal Box

The stars filled the Royal Box (pictured front row, Sachin Tendulkar and his wife Anjali. Second row L Elaine Paige and Anna Wintour and Tom Ford)

Morgan Riddle, partner of Taylor Fritz, also arrived in the player's box prior to his match

Morgan kept cool during the game with an electronic fan

Sir Nick Clegg and his wife Lady Miriam Clegg appeared in great spirits as they posed together

His wife put on a summery display in a button up coral orange summer dress and matching pink sandals

Golda Rosheuvel and Dionne Smith opted for all red and blue respectively

Rami looked in great spirits as he smiled and chatted with fans

Annabel Croft looked stunning in a white dress adorned with a green leafy print

Sophie looked in great spirits as she concealed her blossoming bump in the summer dress

The actor was seen chatting with a pal as he donned a grey jacket and pale pink shirt

Jessica Plumer wowed in an off the shoulder cream statement top and coral red leather skirt

The Bridgerton actress paired her dress with white trainers and a dark brown leather bag

Louis Theroux opted for a pale grey jacket and blue trousers before completing the look with black Converse

Joe Alwyn, Riz Ahmed, Bashy aka Ashley Thomas and Tosin Cole (pictured L-R)

Jessica posed for a snap alongside stylish Carlotta Constant

Actor Daryl McCormack looked stylish in a green and white striped shirt

Riz looked effortlessly cool in the summer ensemble

Indian former international cricketer Sachin Tendulkar looked very smart in a navy suit and brown shoes

He was joined by his wife Anjali

Elaine Paige opted for a colourful white summer dress and matching floral shoes and bag as she beamed in snaps

British boxer Conor Benn opted for a black plaid top and beige trousers

Ben Radcliffe looked dapper in a pale blue shirt and pinstripe black trousers

Former tennis player Bjorn Borg looked on from the royal box

Tessa Thompson cut a stylish figure in a cream and black dress