Wimbledon's Courtside Couture

How champions and spectators alike have shaped tailoring at the world's most prestigious tennis tournament.

Wimbledon's Courtside Couture

As young whipper-snappers holidaying on the Welsh Riviera in 2003, friends and I retired from our casual beach tennis game to watch Roger Federer play Mark Philippoussis in the Wimbledon singles final, where Federer was victorious. At that moment, I witnessed a languid, one-handed backhand that defied the definition of elegance - a stroke that played a more than pivotal role in him becoming the record-breaking eight-time Wimbledon Grand Slam winner. Nowadays, Federer's occasional spectating buddy happens to be Vogue editor Anna Wintour, but the world tennis champion has always carried himself with the utmost natural fluency, which certainly shines through his choice of outfits nowadays in the boxes at Wimbledon.

Photographed by Brandon Hinton with fashion direction by Tom O’Dell for Issue 94 of The Rake.
Photographed by Brandon Hinton with fashion direction by Tom O’Dell for Issue 94 of The Rake.

In July of 1935, Luton Borough Police officers wore straw helmets, horses, carts and drivers paddled in the Thames opposite parliament, and at Wimbledon's No. 1 Court spectators protected their heads from the scorching sun with newspapers or knotted handkerchiefs folded into hats - and it was customary to puff on a pipe. Thirty years later, in the Royal Box on Centre Court, Princess Margaret, the second-daughter of one-time Wimbledon competitor King George VI, carried on the fumatory theme by smoking a cigarette from an elegant long holder, probably designed by Dunhill. 

There was a significant disparity in the climate between 1935 and 1965, with the former being the driest July in history and the latter being the third coldest of the century. However, that was in essence the only difference; in both years, on and off the court, the outfits portrayed a type of stylish self-expression that is somewhat lacking in modern times. Helen Wills Moody, a glamorous American player, won the seventh of her eight singles Wimbledon finals in 1935, and fellow American and opponent Helen Jacobs congratulated her on Centre Court. In only the previous decade restrictive clothing such as petticoats, ankle-length skirts and corsets was the norm. And so when, in 1935, Wills Moody wore a white shirt, a white pleated knee-length skirt, a cerise-coloured cardigan and her iconic fashion accessory, the white eye-shade/visor, it was a truly trailblazing outfit. 

Fast forward to 1965, and the Brazilian-born three-time Wimbledon ladies' singles winner Maria Bueno, nicknamed the "Tennis Ballerina" for the grace with which she moved across the grass of the court, won the doubles title with Billie Jean Moffitt (afterwards Billie Jean King), and she sported an eye-opening outfit featuring undershorts adorned with 14 rows of lace. She was a muse for Teddy Tinling, a tennis player, spy, author and couturier, who not only designed the aforementioned avant-garde piece but, in 1964, when Bueno won her third singles title, Tinling barbed the all-white preference for playing attire by lining her dress with Italian pink. When her skirt flew up after a serve, her knickers were revealed to be the same colour, a legendary tale from Wimbledon.

For ladies' competitors, the aforementioned costumes struck the perfect balance between popularising a new zeitgeist of tennis dress and showcasing impeccable taste, which transferred the right tone of charisma and individuality, the latter of which is not so common today. It’s debatable whether Bueno flouted the dress code, which states that all players have to wear “suitable tennis attire that is almost entirely white.” However, for the spectators, the code, or lack thereof, is not so stringent. For two weeks in July, the All England Lawn Tennis & Croquet Club is akin to Royal Ascot and Henley as quintessentially British, with its tradition of strawberries, cream and Pimm's, as well as its advisable dress code. The truth is that, unlike the Royal Enclosure at Royal Ascot, there isn’t an official Wimbledon dress code, but one should gauge and respect the traditions of SW19 in July and dress accordingly.

Photographed by Kim Lang with fashion direction by Grace Gilfeather for Issue 84 of The Rake.
Oriol photographed by Jake Walters with fashion direction by Jo Grzeszczuk for Issue 60 of The Rake.

Attendees dressed in attire that exudes smart casual respectability with a hint of panache are the elixir of embodying Wimbledon's illustrious British heritage. After serving as the president of the All England Lawn Tennis and Croquet Club for more than 50 years, the Duke of Kent stepped down in 2021. He presented his first of over 350 winners’ trophies in 1969, to Rod Laver, who incidentally was present in the gallery this year, as well as to the "bad boys" Illie Năstase, Jimmy Connors and John McEnroe, and of course Björn Borg (who bucked the trend, being known as the Ice Man) during the 1970s and 1980s, and Andre Agassi, who was only mildly more placid but no less stylish in the 1980s. The reason for name-checking the Duke of Kent is that for Wimbledon dignitaries and audiences in boxes and stands on the show courts of Centre Court and No. 1 Court, one should really construct an outfit bordering on the smart side, and one of those exemplifying this stance nearly every year is the Duke of Kent’s brother, Princes Michael of Kent. 

Prince Michael’s purple and green tie, the Wimbledon colours, is about the only piece of apparel that remains largely unchanged. It isn’t that he alters his formality, but his array of suits and shirts on each visit has been rather commendable. Along with windowpane and herringbone suit patterns, he has sported both black pinstripe and chalk stripe suits in either single or double-breasted guises, and it’s likely that a proportion was cut at arguably the world’s preeminent tailors, Anderson & Sheppard. If it's a chilly July day, a worsted woollen or cotton and wool blend cloth will do. If the weather is as crisp as it was in 1965, you should definitely consider wearing your wool version, paired with a lightweight and breathable white Alumo cotton shirt from Turnbull & Asser. Charles Dance, another former cover star of The Rake magazine, also wore a chalk stripe suit at Wimbledon, and The Rake's own collection offers a similar version.

It wasn’t in the same temperate bracket when a “heat dome” nicknamed Lucifer descended on Europe in 2021, but for the men’s singles final between Novak Djokovic and Nick Kyrgios in 2022, it was the first time that the authorities partially closed one half of the retractable roof to offer some shade. This is likely to be an isolated occurrence, so to dress comfortably and elegantly, one must be knowledgeable about fabrics and have the appropriate accessories. The double-breasted navy blazer is a stalwart garment for getting you out of a spot of bother. Not double-breasted, but Ralph Lauren, who is the Official Outfitter of the tournament’s on-court officials, dresses the umpires in navy blazers, and so by electing a linen blend or hopsack version from Edward Sexton, you’d certainly be adhering to the traditions of Wimbledon. It can be a quandary when to don a Panama hat, but at Wimbledon it’s obligatory, so turn to Lock & Co. Hatters for a wide-brim edition or the classic Crosby boater hat, a product of The Rake x Hat of Cain collaboration.

Dylan Armstrong photographed by John Rowley with fashion direction by Holly Macnaghten for Issue 88 of The Rake.
Raashid Hooks photographed by Kim Lang with fashion direction by Grace Gilfeather for Issue 83 of The Rake.

As alluded to, Roger Federer possesses this approachable yet ethereal disposition, which is only extended by his outfits. He’s known to dabble with unconventional costumes, one of which was a dark navy notch lapel single-breasted suit, a white spread collar shirt, a black tie, and sockless-white sneakers. For Centre Court, I wouldn't be citing this look, but Federer is the master at pulling off such outfits. While I would be hesitant to replicate this look, Stefano Bemer's wholecut sneaker, available in an understated blue marino French suede or off-white, is an excellent choice if you're looking for a sneaker that appeals to Wimbledon. If you're participating on Henman Hill, also known as Murray Mound, pair these sneakers with a pair of sartorial chinos or lightweight pleated trousers from the same brand. If you only have a Ground Pass, a long-sleeve polo shirt from G. Inglese is an excellent option, and don’t forget a cool pair of handmade shades from Oliver Goldsmith.

However, going back to Federer, his 3-pocket beige single-breasted peak lapel jacket and matching trousers are a timeless Wimbledon ensemble. He pairs it with a blue-striped Bengal shirt and a dark-dotted shirt. Federer is renowned to be a client of both the English and Italian schools of tailoring, but should there be a blast of solar radiation before the men’s final on Sunday, you can’t help but favour the Neapolitan style to transmit that smart casual dégagé feeling, the ultimate guise to demonstrate at Wimbledon.