Frank Sinatra and the timeless class of the tuxedo


When it comes to class and elegance, there’s one style icon who has always personified the concept of the real gentleman for the public. Singer, actor, TV presenter, he has charmed entire generations with his voice and charisma, writing an important page in the history of the music of last century. Who are we talking about? The great Frank Sinatra of course!

Fedora, tuxedo, cigarette and a glass of whisky are undoubtedly the four trademarks that identify this truly unique character. “The tuxedo is not a piece of clothing. It’s a way of life”: this was one of his favourite mottoes, testimony of the kind of elegance which was simply a vocation for Sinatra.

Indeed, as a true Italian, he loved to show off his impeccable elegance and wear tailor-made suits with large lapels. He matched his tuxedo – never worn on a Sunday – with a white tuxedo shirt buttoned up to the top and with the wristbands showing about a centimetre from the sleeves of the jacket. He would then enhance his tuxedo shirt with his ever-present cufflinks and bow-tie. The gentleman’s outfit was then completed by a three-button Glen plaid coat with a split in the middle at the back, a narrow-brimmed hat worn at an angle and black derby shoes, constantly and meticulously polished until they shone.


However it was Frank Sinatra himself who revealed the secret behind this touch of class, which reads like a real handbook on elegance to the general public. The ideal tie colour for all occasions? Strictly black, unless the invitation requests a specific shade.

“My basic rules are to have shirt cuffs extended half an inch from the jacket sleeve”, while trousers “should break just above the shoe. Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favourite colour”. 

When the sun went down, his chosen menswear never sported shades of brown, white, grey or blue, unless it was midnight blue: after sunset, a gentleman always chose black, with ties that had to be silk.

The most paradoxical thing of all about the history of the tuxedo, the most elegant garment of the man’s wardrobe adored by Sinatra, is that it was actually conceived as a jacket for relaxing in, a more casual and comfortable alternative to the dress suit, designed to meet the desperate longing of the King of England, Edward VII, for a garment that would allow him to feel comfortable as he smoked after dinner.

Who would ever have thought it?

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