The most stylish celebrity moments at Wimbledon through history

30 June 2023

With a slew of celebrities descending upon SW19 each year, fashion is the second spectator sport at the Wimbledon Championships.

While some celebs stick to traditional all-white ensembles, others stand out with bold colours and prints.

From royals to rappers, here are some of the biggest fashion moments from Wimbledon throughout the years…

Queen Elizabeth II

Patron of the All England Lawn Tennis and Croquet Club club from 1952 to 2016, the late Queen only made a few appearances at Wimbledon over the decades.

In 1957, the young Queen awarded the winners’ trophies in a typically Fifties look: a flowing floral midi dress with a white hat, gloves, handbag and peep-toe heels.

Diana, Princess of Wales

A regular at Wimbledon, Diana went through something of a fashion transformation in the Nineties.

Her outfit from 1994 – a red belted dress with gold buttons – is a perfect example of Diana’s sleek style following her separation from Prince Charles.

The Beckhams

David Beckham is seen at Wimbledon almost every year – always looking dapper in timeless tailoring – and in 2014 he attended with wife Victoria, who wore a multicoloured mini dress from her eponymous fashion label.

Beyonce and Jay-Z

Music power couple Beyonce and Jay-Z got the Wimbledon whites memo in 2016.

Watching pal Serena Williams on Centre Court, Queen Bey wore a mini dress with lace detailing, while Jay-Z kept it casual in a white tee and black baseball cap.

Anna Wintour

Self-confessed tennis fanatic and editor-in-chief of Vogue Anna Wintour is another Wimbledon regular and always dresses for the occasion.

In 2017, she swapped her usual colourful floral frocks for a white tweed empire line dress (likely a Chanel design) topped with her trademark black sunglasses.

Emma Watson

A bumper year for Wimbledon fashion watchers, 2018 saw Harry Potter star Emma Watson giving us a masterclass in androgynous tailoring when she donned an ivory three-piece suit and matching hat.

Kate and Meghan

Sitting together in the royal box in 2018, the then-Duchess of Cambridge and the Duchess of Sussex chose summery ensembles, Kate in a black and white spotted dress and Meghan in a blue and white stripey shirt with a cream skirt and hat.

Drake

Bringing streetwear style to SW19 in 2018, rapper Drake wore a green slogan hoodie from his fashion brand Ovo.

Sienna Miller

Harking back to her early Noughties heyday, in 2022 actor Sienna Miller chose a boho-style white broderie anglaise dress from Ralph Lauren with a black belt and snake print heels.

Gemma Chan

Serving up sporty style last year – in Wimbledon colours, no less – actor Gemma Chan donned a green checkerboard print Louis Vuitton dress and a handbag, also from the label, with a tennis ball-yellow charm.

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