Played on outdoor grass courts, The Championships, Wimbledon is the world’s oldest tennis tournament. Every English summer, celebrities, socialites, royals, and the public gather to watch the matches with the best players in the world. Let’s take a look at Wimbledon’s best dressed men this Wimbledon 2019.

James Middleton

The Duchess of Cambridge’s brother, James Middleton, attended Wimbledon with their sister Pippa wearing a series of stylish outfits. On one day, he wore a grey double-breasted wool suit with a light blue button-up shirt and navy tie. He wore grey suede loafers and grey socks. These kinds of loafers are very popular in menswear this summer.

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James Norton

Actor James Norton is known from his Grantchester days as well as Death Comes to Pemberley, Happy Valley, War and Peace, and McMafia. At Wimbledon, he wore a green wool blazer, a white button-up shirt, black tailored trousers, and accessorised with a brown belt, brown shoes, and a flashy watch.

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Eddie Redmayne

Actor and Oscar winner (for his portrayal of Stephen Hawking in The Theory of Everything) Eddie Redmayne is no stranger to sharp dressing. He and his wife, Hannah, attended Wimbledon where he wore a Ralph Lauren Purple Label suit. The suit was in a dapper grey-blue linen. The trousers are tailored in a slim fit and the slimmer lapel allows Redmayne’s chest to appear broader. He wore a white shirt underneath with a navy tie and a white pocket square with navy edging. He wore dark brown shoes and a black leather strapped watch.

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Jack Guinness

Cambridge-educated author and former model Jack Guinness looked ready for summer wearing linen trousers and a double-breasted striped blazer, a casual white button-up shirt. He paired the snake-emblazoned Gucci loafers with some reflective sunglasses.

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Bradley Cooper

A Star is Born actor Bradley Cooper, showed up to Wimbledon looking dapper in a navy tailored single-breasted suit. He wore a blue button-up shirt and matching navy tie with polka-dot detailing.

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Douglas Booth

English Douglas Booth, known for his roles in Great Expectations, And Then There Were None, and The Pillars of the Earth, wore a windowpane patterned single-breasted navy suit by Polo Ralph Lauren. He paired the look with grey leather loafers and a well-fitted casual white t-shirt. He hung his tortoiseshell sunglasses from his pocket too!

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Stormzy

If you wanted to see more casual tailoring to attend the tennis match, look no further than British rapper Stormzy. He wore a look from Burberry, a navy blazer with thin notched lapels, slim fitting and single breasted. Underneath he wore a casual white t-shirt, blue denim jeans, and finished it off with white trainers.

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Johannes Huebl

Model, photographer, shoe designer, and now husband of Olivia Palermo, Johannes Huebl wore a tweed grey notched lapel blazer with summery white tailored trousers, wool socks, and brown leather shoes. He wore a burgundy striped button-up shirt, a silk white and tan checkered pocket square, and a green tie with subtle white fleur-de-lis. He finished the look with Tod’s sunglasses.

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Which outfit would you wear?

Which of these looks is your favourite? Would you wear a full, three-piece suit to Wimbledon or go more casual with tailoring plus a t-shirt? Whatever your next event, we can create a custom look just for you. Contact our tailoring team today.

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Elaine Frieman

Elaine Frieman

Writer and editor from both sides of the pond with a Master's degree in British Victorian Literature and a love of fashion. Elaine Frieman is a dual British and American citizen (with a generic American accent); she has a love of people, travel, reading, writing, food, ballet, theatre, and cultures. And who doesn't love a good suit? She spent her childhood near the rolling green Pennines in the North of England; then she relocated to sunny palm-tree-laden Florida and moved further north to the deep-South Bible belt of Georgia. She currently lives in Todmorden, England with her boyfriend Michael, after having lived in Florida, Georgia, Minnesota, Weiden in der Oberpfalz, Germany, and in Oldham, England. No plans to relocate any time soon.