Happy birthday, Frank Sinatra

Categories Lifestyle

Few names whisper ‘style’ quite like ‘Sinatra’, who would’ve turned 101 years old today. To celebrate, here are Ol’ Blue Eyes’ five style signatures.


Singing with Bing Crosby and Dean Martin in the aptly named hit ‘Style’, the crooner offered, ‘You either got or you haven’t got style. If you’ve got it, you stand out a mile’. And what made Sinatra stand out a mile? His flawlessly tailored suits throughout an era when denim was sweeping American pop culture, from his oversized windowpane suits of the 1940s to the wide lapel jackets of the ’50s then the slimmer suits of the swinging ‘60s.



While he wasn’t shy to experiment with blue, pinstripe and plaid suits in the daylight hours, Sinatra’s golden rule was to wear black after dark — and that meant donning a tux of an evening, usually favouring a vest to a cummerbund. “For me, a tuxedo is a way of life,” he said. “When an invitation says black tie optional, it is always safer to wear black tie.”



Sinatra’s defining style hallmark is the tilted hat, the brim on the back curled up and the front hovering  a couple of inches above his brow. Although the fedora (and the thinner-brimmed trilby) are now the preserve of shiny suit-wearing race-goers and basement-dwelling video-gamers, the Sultan of Swoon pulled it off with that trademark angle — again from Style, ‘A hat’s not a hat till it’s tilted’.



A Sinatra outfit isn’t complete without subtle cufflinks and a perfectly folded pocket square — “Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favorite colour.” The Voice wasn’t big on jewellery but was rarely spotted with a naked cuff, favouring monogram cufflinks.



He might have been sharply dressed but Sinatra didn’t see the need for anything fancy with his shoe-shining routine — his famous tip was to “shine your Mary Janes on the underside of a couch cushion.” Like his suits, The Chairman of the Board preferred his shoes black, favouring hand-crafted pairs of classic lace-ups produced by prestigious Italian shoemaker Berluti.