Bing Crosby carried a lot of feathers in his cap. As one of the first stars to straddle the music and movie business with equal success, Crosby was a preeminent force in American pop culture in the first half of the twentieth century, from Prohibition and the Great Depression through WWII and the post-war boom. A pioneering singer who could seemingly turn his mellow vocal talents to any genre, Crosby had a voice described by no less a figure than Louis Armstrong as being ‘like gold being poured out of a cup’. On screen, he was the ultimate everyman — not a matinee idol or a brawny victor, but a more humble hometown hero: friendly, easy-going, decent, and hopeful. His biographer, Gary Giddins, in reference to his chameleon’s ability to remain relevant across decades and generations, writes that: ‘If Churchill, in his Savile Row pinstripes with his cigars and learned oratory, incarnated the British lion, Bing, in his peculiar motley (shirttails, beat-up hats, torn sweaters, mismatched socks) with his pipe and preternatural calm, embodied the best in American individualism’.
It’s an image that speaks to the extent of Crosby’s unique and near-universal appeal, but also points to one of his eccentricities, namely the way he dressed. By all accounts, Bing had a rather chaotic sense of style. His clothes were often scruffy, awry, and strikingly ill-matched. The latter was largely down to his colour blindness. As Giddins recounts:
‘Bing’s clashing clothes […] became a running gag, as much a part of the Crosby persona as Jack Benny’s cheapness — though, in this instance, grounded in reality. Bing could not tell red from green; he was able to drive because traffic lights were all the same to him — red on top, green on bottom. [His writing partner Carroll] Carroll recalled once pointing out to Bing that he was wearing different socks, black and red. Bing looked down and replied, “That’s funny. They both fit.” Asked on another occasion if he knew the color of his socks, Bing answered, “Dark?”’
Regardless of this disability — or perhaps because of it — Crosby embraced a chaotic sense of colour in everything he wore, from Hawaiian shirts and striped jackets to motley plaids and bold checks. Another anecdote recalls him buying a bolt of green doeskin cloth while on holiday in Bermuda to have a suit made for a friend. ‘How’s that for a nice green?’ Crosby asked when he brought it back to his lodgings. ‘That’s swell, Bing,’ his friend told him, ‘but it isn’t green. It’s pink, and a bad pink at that.’ Bing dutifully returned to the store to exchange it, but this time chose to order by name rather than sight.
Surely the most famous apparel anecdote involving Bing Crosby, however, was a certain all-denim ensemble that is putatively the origin of the term ‘Canadian tuxedo’. Back in 1951 while on a hunting trip with a friend, Crosby was barred entry from a swanky Canadian hotel for wearing head-to-toe denim. Fortunately, a bellhop recognised him and he was granted entry, but news of the incident reached Levi’s and they proceeded to make the entertainer a tuxedo jacket made from the same selvedge denim as his 501 jeans. It also came complete with a red tab mock corsage and a corresponding label that read: ‘Notice: To hotel men everywhere. This label entitles the wearer to be duly received and registered with cordial hospitality at any time and under any conditions.’ It was presented to Crosby in Elko, Nevada where he was honorary mayor, and it rose to cult status after he wore it during press events for an upcoming film. It remains such a well-told story that Levi’s Vintage Clothing even reissued a limited run of 200 repo denim dinner jackets back in 2014.
These anecdotes endure in part because they illustrate Bing Crosby’s good humour about his appearance. This sensibility also extended beyond his dress sense. Crosby, who had a small build and average looks by showbiz standards, proved unusually sanguine about Hollywood’s exacting beauty standards. He refused, for instance, to have his ears flattened surgically despite being prompted to do so by his employers and instead endured the extensive and painful business of having them glued back daily in the make-up chair. Ditto, despite balding early on in his life and wearing a hairpiece on camera when a hat wouldn’t do, unlike many of his contemporaries, Crosby never concealed his hair loss and happily appeared sans toupée in public. Per Giddins, ‘Errol Flynn was so amused by Bing’s willingness to attend sporting events, restaurants, and parties without a rug that he once walked over to his table and planted a (photographed) kiss on top of Bing’s bare head.’
Looking at photos of Crosby throughout his career, it seems odd in a way that he would so often be described in comic terms in matters of appearance — sometimes even in the roles he played. The passage of time, perhaps, or the monochrome effect of black and white photography, tends to leave Crosby not looking all that different from his showbiz peers. Moreover, from a contemporary perspective, Crosby’s aesthetic demonstrates an unpolished sense of recklessness that would not look out of place in the lookbooks of many of today’s best-loved streetwear brands. His golfing outfits in particular, feel infinitely imitable, with his slouchy cardigans, the slightly dishevelled polo collars, the cheekily cocked bucket hats and trilbys, and that pipe perennially poking out the side of his mouth. He comes across as a man who is very much at home in his own skin and his casual clothes most aptly suggest as much. We should all be so lucky.
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