The world would be a boring place if we all dressed just like our mates; here we celebrate a handful of our favourite odd couples.

So many trends in menswear have a uniform — be it mods, rockers, or new romantics. Where things get interesting, however, is when a gentleman who has a well-defined personal style starts palling around with someone who dresses to the beat of a different drummer. Consider that 1977 TV special, Bing Crosby’s Merrie Olde Christmas, where Mr Crosby, looking as if he just stepped off the golf course in a powder blue cardigan, duets on a mash-up of “Peace on Earth” and “The Little Drummer Boy” with the glam Mr David Bowie. FYI: Mr Bowie did the show because his mum loved Crosby’s music.

Sartorial juxtapositions like Bowie-Crosby put each participant’s personal style in sharper relief, while giving the rest of us a clue about how to broaden our own horizons. So in the interest of picking up some new style moves, we take a look at our favourite disparate duos.

Even though Sir Churchill would become a frequent guest on Mr Onassis’s yacht, the Christina O, the two friends approached dressing from different mindsets — the British statesman and the Continental tycoon. As a young man serving under Lord Horatio Herbert Kitchener in the Sudan, Sir Churchill had worn the uniform of the 21st Lancers, and as an elder statesman, he still dressed formally even in balmy climes. Mr Onassis wore the suitings of a boulevardier or terrycloth polos, swim shorts and espadrilles. So even when the occasion called for both to be dressed up, theirs was a Continental vs British play-off with Sir Churchill in Savile Row suits, Turnbull & Asser shirts and George Cleverley shoes vs. Mr Onassis in Caraceni suits and his statement eyewear from Paris’ Bonnard and from François Pinton.

The most celebrated baseball player and the most popular singer of their generation had much in common. Both were the children of Italian-American immigrants and both were married, then jilted, by luscious starlets — Ms Marilyn Monroe and Ms Ava Gardner, respectively. Still, their friendship was complicated. In the above image from March 1949, the relationship is new. Mr DiMaggio is at the beginning of what would be a championship season, and wears the classic pinstripe uniform of the New York Yankees. Off the field, Mr DiMaggio dressed conservatively and All-American. This is perhaps a subconscious reaction to the fact that his parents, along with thousands of other Italian, German and Japanese Americans, were classified as “enemy aliens” by the government after the bombing of Pearl Harbor. Mr Sinatra felt no such need for understatement, appearing here in a double-breasted, peak lapel suit — if only sports fans put such care in what they wore to the ballpark today.

What man wouldn’t want Mr Fred Astaire to play him in a film? In Funny Face, a musical set inside the fashion world, Mr Astaire plays a photographer named Dick Avery, loosely based on Mr Richard Avedon who acted as a technical advisor on the film. Mr Avedon always dressed classically, despite growing up in Manhattan as the child of two parents in the fashion industry. Here he is pictured in a Brooks Brothers button-down, a crew neck sweater and a mackintosh. Mr Astaire, who patronised Anderson & Sheppard, Hawes & Curtis, and would “get lost for days in the Burlington Arcade”, was a master of looking casual in well-made clothing. His trilby hat is the perfect bit of sartorial sunshine on a rainy day.

By 1972, Mr Groucho Marx was divorced for the third time and living in Beverly Hills. He, like many in the entertainment business, felt very staunch against the war in Vietnam and was a supporter of the Democratic presidential candidate, Mr George McGovern. In his later years, he had dropped some elements of his on-screen persona (the tailcoat with necktie) in favor of a look more suited for a French philosopher at Les Deux Magots: a beret and a blazer worn over a crew neck sweater. Like Mr Marx, Mr Nicholson enjoys a good cigar, but on style they part company — Mr Jack Nicholson is seen here in white overalls and a multicoloured short-sleeved shirt.

During a 1931 tour of America, Mr Albert Einstein, who is still a German citizen at this time, was introduced to Mr Charlie Chaplin during a tour of Universal Studios. The two developed an immediate rapport. “What I admire most about your art is the universality,” Mr Einstein said to Mr Chaplin. “You do not say a word, and yet… the world understands you.” To wit, Mr Chaplin replied, “But your fame is even greater. The world admires you, when nobody understands you.” Mr Chaplin invited Mr Einstein to be his guest at the premiere of his new film, City Lights, a few evenings later. While both sported a butterfly collar on their tuxedo shirts, they provide a snapshot of two different approaches to black tie: Mr Chaplin in a peak lapel jacket and Mr Einstein in a shawl collar with a horseshoe waistcoat.

The image was taken in 1977 at Mr Muhammad Ali’s training facility in Deer Lake, Pennsylvania, where the boxer was preparing for his fight against Mr Earnie Shavers. Mr Andy Warhol, who was working on his “Athletes” series, was not a natural sports fan, but he was fascinated by the loyal following athletes commanded. “His problem is he's in show business,” he said of Mr Ali to the author Mr Victor Bockris, who had accompanied him that day and took the above image. “I'm surprised fighters don't take drugs, because it's just like being a rock star. You get out there and you're entertaining thirty thousand people.” The two provide a beautiful contrast in styles. Mr Ali was fresh off a two week European tour wearing black from head to toe. Mr Warhol delivers a bit of preppy summertime perfection in a seersucker, oxford cloth shirt and a repp tie.

One dresses for sun; the other for rain. When the British artist, Mr David Hockney, did a series of lithographs of the American writer, Mr William S. Burroughs, in 1981, he had already left England and was creating sun-drenched masterpieces from his house-cum-studio in Los Angeles’ Nichols Canyon. During those years, his dress was always that of a perennial school boy, putting a technicolour and cheeky spin on the classics — be it a candy-striped dress shirt with a knit tie, or a panama hat and jaunty pocket scarf — as he does to add some flair to his suit when the two reunite in the above image taken at the Naropa Institute, Boulder Colorado in 1989. Mr Burroughs' harrowing accounts of addiction including Junky and Naked Lunch. Yet he dressed conservatively. While many of his fellow Beat Generation writers preferred workwear, Mr Burroughs appeared in public as one would expect the scion of a wealthy St. Louis family to. His grandfather was the founder and inventor of the Burroughs Corporation, a major manufacturer of business equipment. Mr Burroughs fondness for three-piece suits, tweed coats, argyle sweaters, chesterfields and trench coats make him look no different than any other Harvard man of his generation — except perhaps his fondness for his hard-boiled fedora which became something of a signature in his later years.

None of the celebrities featured in this story is associated with or endorses MR PORTER or the products shown