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The Tribute

The Men Who Looked Cool While Sweating It Out

The icons who wore sportswear with effortless style

  • Mr Muhammad Ali jogging at his training camp in Deer Lake, Pennsylvania, US, c. 1980. Photograph by Mr Peter Angelo Simon/

Over the decades, there have been figures who have put their own spin on sportswear. Take the Duke of Windsor, who was known for paying as much attention to his accessories as he was to his clubs when setting out on the golf course. But also athletes, such as Mr Muhammad Ali, pictured above, who brought with them a sense of style to the sporting arena. Scroll down to find other luminaries who have brought their A game to the blending of streetwear and sportswear, and who may well have been first past the post when it came to inventing the concept of athleisure, years before it became a bona fide, all-conquering thing.


  • Mr Bob Hope fishing from a boat in the 1940s. Photograph by Hulton Archive/Getty Images

Harking back to a kinder, gentler comedic era, when “roasting” meant an unhurried lunch of chicken Parisienne and a martini or three at Chasen’s, Mr Bob Hope shows all the off-duty savoir faire you’d expect of Old Hollywood royalty. Golf may have been his preferred leisure activity – he once quipped that he couldn’t give it up because he had too much money invested in sweaters – but he was also no slouch when it came to fishing attire. Witness the discreetly logo’d captain’s cap, the soft plaid shirt, the loose-cut chinos, the spiffy deck shoes and, above all, the let-the-marlin-come-to-me sense of lofty detachment. We’re falling for it hook, line and sinker.

Get the look

  • A.P.C. Felix Checked Cotton and Linen-Blend Shirt

  • Albam Wide-Leg Cropped Pleated Cotton Trousers


  • The Rolling Stones at Swarkestone Pavilion, Derbyshire, c. 1968. Photograph by Mr Michael Joseph/Raj Prem Collection at Camera Press

How do you blow off some steam if you’re recording your latest opus in the depths of the British countryside? If you’re The Rolling Stones, and it’s the tail end of the 1960s, you organise an impromptu cricket match in the grounds of the studio, while making no compromise on style. You note, in fact, that candy-stripe blazers and trousers, along with silk cravats and floppy fedoras, team rather well with cricket whites and take a devil-may-care attitude to grounds keeping, fielding positions, bat placement and piano-as-wicket maintenance. Less silly mid on, more fine leg.

Get the look

  • Gucci Slim-Fit Striped Wool and Cotton-Blend Suit Jacket

  • Borsalino Grosgrain-Trimmed Straw Panama Hat


  • Mr Steve McQueen in the Paramount Studios gym, 1963. Photograph by Mr John Dominis/The LIFE Picture Collection/Getty Images

Not everyone can look ineffably cool while bench-pressing 80lb, but then not everyone can be Mr Steve McQueen, foremost style icon, who, even while minimally attired on the Paramount Studios lot in 1963, manages to anticipate a brace of key post-millennial menswear trends, namely the lush jogging pant and the minimally sleek sneaker. If you’re going to emulate this look – and we strongly suggest that you should, whether you’re hoisting 80lb or facing down 80oz – don’t forget that, as well as the clothes, the “I live for myself and I answer to nobody” expression is key.

Get the look

  • Reigning Champ Slim-Fit Loopback Cotton-Jersey Sweatpants

  • Common Projects BBall Leather Sneakers


  • Mr Dustin Hoffman at the RFK Pro-Celebrity Tennis Tournament, New York, 1973. Photograph by Mr Ron Galella/Getty Images

Ah, the glory days of the tennis circuit in the 1970s, when Mr Björn Borg and Mr Vitas Gerulaitis would pause just long enough from making the intimate acquaintance of a supermodel and/or polishing off a packet of Marlboro Lights to pull on their form-fitting polo shirts and short shorts, brandish their teeny wooden rackets, and conquer all-comers at Wimbledon or the French Open. Mr Dustin Hoffman, here doing the pro-celebrity honours at a New York tournament in 1973, is retro-fitted to a tee, right down to his towelling socks and no-frills sneakers. When it comes to a look that’s inspired everyone from Mr Wes Anderson to Mr Pharrell Williams, the score is always love all.

Get the look

  • Lacoste Cotton-Piqué Polo Shirt

  • Nike Tennis NikeCourt Flex Ace Slim-Fit Dri-FIT Tennis Shorts


  • Mr Muhammad Ali jogging at his training camp in Deer Lake, Pennsylvania, US, c. 1980. Photograph by Mr Peter Angelo Simon/

“I hated every minute of training,” said Mr Muhammad Ali, “but I said to myself, don’t quit. Suffer now and live the rest of your life as a champion.” And, he might have added, suffer that little bit less by donning a superlative training outfit – a long-sleeved muscle tee and a pair of sturdy track pants to keep out the early-morning chill, plus a statement timepiece that knocks any Fitbit or similar into a cocked hat – to confirm that, in helping to inspire today’s haute exercise/everydaywear, he remains The Greatest. As Mr Ali himself put it, “It’s not bragging if you can back it up.”

Get the look

  • Brunello Cucinelli Fleece-Back Cotton-Jersey Sweatshirt

  • TAG Heuer Carrera Automatic Chronograph 43mm Polished-Steel Watch

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MR PORTER or the products shown