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The Tribute

Seven Of The Best Sailing Outfits Ever

All aboard with Mr Paul Newman, Mr Alain Delon and President JFK, the guys who were always dressed to keel

  • Mr Alain Delon filming The Last Adventure at Fort Boyard, France, 1967. Photograph by Mr Tony Frank

Summer’s practically upon us, and our thoughts are naturally turning to seasonally appropriate pursuits: alfresco martinis, the search for a well-turned sandal and a Mediterranean idyll at the helm of a Riva 88’ Domino superyacht. Admittedly, the first two may be slightly more achievable than the third, but we can at least ensure that we’re dressed for the sun deck, should any invitations arise, by following the lead of the waterborne exemplars below, who never saw a mainbrace they couldn’t splice, and who never looked less than ship-shape while doing so. Gentlemen, take a bow. 


  • Mr Errol Flynn and Ms Lili Damita, c. 1940. Photograph by Mr George Rinhart/Corbis via Getty Images

You’d expect old-school Hollywood royalty such as Mr Errol Flynn to look as perfectly, well, correct when taking to the water as in any other area of their finely honed lives, and Mr Flynn doesn’t disappoint here on his (admittedly fairly minimalist) boat. Ever the gent, he’s passed his captain’s cap to his first wife, the French film star Ms Lili Damita, while keeping the offshore breezes at bay himself courtesy of a generously proportioned ribbed-wool zip-up cardigan that anticipates today’s oversized trend by a good seven decades. Meanwhile, Arno, Mr Flynn’s schnauzer, proves the ultimate in stylish accessories, while keeping a beady eye out for the flying fish he apparently loved to chase.

Get the look

  • Brunello Cucinelli Slim-Fit Mélange Cotton Zip-Up Cardigan

  • Etro Slim-Fit Washed Stretch Linen and Cotton-Blend Trousers


  • Mr Jacques Dutronc in Hong Kong, 1969. Photograph by Mr Jean-Marie Périer/Photo12

Mr Jacques Dutronc, the famously insouciant pop star and actor, effortlessly keeps his cool in Hong Kong harbour in 1969 in the face of a barrage of “never mind the junk, feast your eyes on the quality of that outfit”-style gags. He looks primed for a soirée on a sloop – if not a few cups of sake on a sampan – in a lightweight linen blazer coupled with the kind of louche, Riviera-ready shirt that a lesser man would have slashed to the navel, and the boxiest 1960s-style statement eyewear this side of Sir Michael Caine. One of Mr Dutronc’s biggest hits was Mini, Mini, Mini, but this is tropical élan carried off to the max.

Get the look

  • Rubinacci Blue Slim-Fit Unstructured Herringbone Linen Blazer

  • Giorgio Armani Camp-Collar Striped Cotton Shirt


  • Mr Jean-Paul Belmondo on the Côte d’Azur, France, 1965. Photograph by Ms Gamma Rapho

Ah, the Côte d’Azur in the mid-1960s. You’re France’s biggest movie star, thanks to your epoch-making turn in Mr Jean-Luc Godard’s Breathless, so how do you rock up for a marina-side lunch, doubtless consisting of a perfectly blended bouillabaisse and a round of bellinis? If you’re Mr Jean-Paul Belmondo, you arrive at the wheel of a beautifully buffed Riva, with a bunch of beautifully buffed and bouffanted chums in tow, secure in the knowledge that you can parallel park with impunity and that any nominal dress code will be modified to “no jacket required and snazzy swim shorts positively encouraged” just for you.

Get the look

  • Barton Perreira + Allied Metal Works Tortoiseshell Acetate and Gold-Tone Polarised Sunglasses

  • Missoni Mid-Length Printed Swim Shorts


  • Mr Marcello Mastroianni in Divorce Italian Style, 1961. Photograph by Mondadori Portfolio/Bridgeman Images

Here is Mr Marcello Mastroianni, in 1961’s Divorce Italian Style, approaching that parlous state with the same ineffable sense of brio with which his countrymen approach anything that life can throw at them. And what, after all, says “time to move on” better than a rakish ’tache, a camp-collared, bold-print shirt, some deck-appropriate pleated linen trousers and one hand on the rigging as you’re borne off to pastures – or should that be inlets – new? We like to think that the happy tune he’s whistling is Mr Jimmy Buffett’s “Something ’Bout A Boat” (“Sittin’ on the sea/ Out there in the wind/ Floatin’ on the free…”)

Get the look

  • Gitman Vintage Camp-Collar Printed Cotton-Poplin Shirt

  • Massimo Alba Watercolour-Dyed Striped Linen Trousers


  • President John F Kennedy in Narragansett Bay, Rhode Island, US, 1962. Photograph by Mr Robert Knudsen. White House Photographs. John F Kennedy Presidential Library and Museum, Boston

Look no further. Ultimate on-deck style was set by President John F Kennedy on board his 62ft cutter-rigged Bermudan yawl Manitou, AKA “the floating White House”, back in the early 1960s. The navy polo, white cotton trousers, towelling socks and deck shoes have since been referenced by everyone from Mr Ralph Lauren to Mr Leonardo DiCaprio in The Wolf Of Wall Street and Jay-Z in the “Big Pimpin’” video, but the President remains unmatchable for chutzpah, from the hand-on-the-tiller man-of-destiny pose to the sunken bathtub he had installed in the aft cabin (said to have been patronised by, among others, Ms Marilyn Monroe).

Get the look

  • Polo Ralph Lauren Slim-Fit Washed Cotton-Piqué Polo Shirt

  • SALLE PRIVÉE Gehry Cotton and Linen-Blend Chinos


  • Mr Paul Newman in Cyprus, 1960. Photograph by Mondadori Portfolio/Bridgeman Images

Frankly, you could place the imperial-phase Mr Paul Newman next to any conveyance of your choice – a pogo stick, a penny farthing, the racing cars he loved – and he’d still look like the epitome of laid-back cool. But there’s something about a boat – such as the immaculately weathered ketch he’s pictured with here, during a break while filming Exodus in Cyprus in 1960 – that suits his blue-eyed, balmy-breeze brand of charisma to a tee. Particularly when it’s accessorised by the perfect fitted-yet-floaty white shirt and a pair of rolled-up chinos. All this, and impeccable rudder action to boot.

Get the look

  • AMI Slim-Fit Button-Down Collar Cotton Oxford Shirt

  • The Workers Club Slim-Fit Garment-Dyed Cotton-Twill Chinos



  • Mr Alain Delon filming The Last Adventure at Fort Boyard, France, 1967. Photograph by Mr Tony Frank

Legs apart, hands thrust into his pockets, a crisp white shirt on his back and a blue jumper slung negligently around his neck – Mr Alain Delon looks like the cat that’s got the cream here. And indeed, he probably had cream in abundance at this point. The French film star was then at his peak as a screen idol and all-round sex symbol powers, pictured on set of the film The Last Adventure at Fort Boyard in France in 1967. Has a cooler man ever walked the Earth (or ridden its waves)?

Get the look

  • Aspesi Cotton-Poplin Shirt

  • John Smedley Theon Slim-Fit Sea Island Cotton and Cashmere-Blend Sweater


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