Frank Sinatra’s defining style moments

With May 14 being the 18th anniversary of Frank Sinatra’s death, it only seems right that we spend a bit of time talking about one of the world’s most beautifully-dressed gentlemen. As talented as he was neurotic – and not without his own personal struggles – Sinatra was an icon like no other and a man who knew how to very easily transform himself into the best-dressed man in the room. Here are some of his best moments:

1958, at Capitol Records

If there’s ever a man who’s going to rightfully pull off the suit, no matter what occasion he’s at, it’s Frank Sinatra. Always slightly oversized – in the best kind of way – and never dressed down with anything other than a tie, sharp shirt, shiny pair of shoes and a trilby. Sinatra nailed it time and time again. He dressed in an expectant, waiting-for-the-camera kind of way every day of his working life – and it paid off. He’s since become an icon of our time, one of the best-dressed men to have ever graced the industry.


(Photo: Capitol Records)

1960, on holiday

For Sinatra, there was no real style that can actually be used to describe the way he dressed. It was all or something else in between – whether that was a full-on three-piece suit and tie, a stained shirt or a more casual, open shirt look. One item that always, without fail, stayed intact was his epic collection of hats. A trilby, fedora or a panama – you name it, Sinatra owned it. And every hat he owned remained beautifully perfect.


(Photo: unknown)

With his T-Bird, 1955

This is the perfect example of Sinatra looking slightly more casual – although it’s not a get-up most of today’s gentlemen would consider casual. From head to toe, he looks every inch the gentleman without looking like he’s trying too hard. The slightly open shirt, the perfectly placed trilby, the length of his trouser. Everything about Sinatra was always just-so, in a manner that no one else did before him and no one else has done since.


(Photo: Frank Worth)

At the 1954 Academy Awards

No article like this would be complete without mentioning Sinatra’s incredible penchant for a decent black tie suit. And the 1955 Academy Awards were no exception – Sinatra pulled off the perfect white bow tie and impeccably coiffed hair like no one else. This was the night that he won Best Actor in a Supporting Role for From Here to Eternity and it’s fair to say that he was very much dressed to impress.


(Photo: Getty)

(Main and featured image: still from Pal Joey)

Channel your inner Sinatra:

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India Gladstone

India is the Online Editor of Gentleman's Journal

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