A performer, an icon, a legacy, a maverick. Few men in history have or will find themselves so admired and emulated as Frank Sinatra. This year marks a century since the entertainer's birth - a milestone which firmly underscores his status as an undisputed icon. To celebrate the centenary of Sinatra, a new multi-media concert has arrived at the London Palladium. Running from the 10th of July to the 10th of October, Sinatra: The Man & His Music will feature all of Frank’s greatest hits, such as Fly Me To The Moon, My Way and New York, New York. Here though, we celebrate the style of a man who has provided endless sartorial inspiration for generations of men, and one who no doubt will continue to do so for some time yet.


The man who would become the Frank Sinatra began life as Francis Albert Sinatra, the son of Italian immigrants in New Jersey, America. Showing an aptitude for performing from a young age, Sinatra began singing in the streets aged 8 and continued to pursue entertaining throughout his formative years, culminating in his first bona fide musical venture as part of a local singing group aged 20. The rest is pop culture history.


Life imitated art for a man who sang 'you've either got or you haven’t got style, if you've got it you stand out a mile'. Just as he cut a sharp figure on screen, off screen Sinatra had that sartorial sensibility that lent itself so well to being captured, pored over and emulated time and and time again.

But, what were the elements of Sinatra's style that caused it to resonate with generations of men? Perhaps the most appealing part of the entertainer's dress sense was his appreciation of fine tailoring, and the knowledge that in the right suit, you'll never be underdressed. Tailor-made suits formed the backbone of Sinatra's wardrobe, and these were worn for all manner of occasions, each with equally slick effect.

Of course, it wasn't just Sinatra's silently sharp tailoring that characterised his style, it was his equally impressive array of fedora hats - cocked just so - that continue to define his image. And it's no surprise, as in his heyday Sinatra was rarely seen without his signature fedora. Mr Sinatra's expertise at wearing a hat - without letting a hat wear him - proves his worth as one of menswear's greatest ever dressers.

For Sinatra dressing was a performance, an attitude and a way of life. The sharpness of his off-duty style was indistinguishable from the guises he adopted on screen.


It's hard to overstress the importance of Sinatra's approach to dressing, not only did he provide a stellar sartorial example among his contemporaries, but his approach to dressing continues to be a template of sophisticated masculinity which has far outlasted the man himself.

What are the lessons to learn from Mr Sinatra? There are many. And there is nobody more qualified to expense sartorial advice than the man himself.

When I started singing in the mid-1930s everybody was trying to copy the Crosby style… It occurred to me that the world didn't need another Crosby. I decided to experiment a little and come up with something different."


Channel the spirit of Sinatra by adopting the star's fondness for sharp tailoring and love of fine details while making the look your own. Take your tailoring in a modern cut for a contemporary approach and don't forget timeless accessories to complete your outfit.

What to wear: The Salt blue panama hat, the Trevor black Derby shoes, the George blue slim trousers, the Exmouth blue linen tie, the Redknapp white shirt, the George blue slim blazer


Housed at the iconic London Palladium, Sinatra: The Man & His Music, brings to life all of the pizzaz, finesse and style that Sinatra possessed.

To celebrate, Times+ is giving one lucky member two tickets to the show, a £1,000 personal shopping experience at Reiss, dinner and a night at the five-star Atheneaum Hotel & Apartments Mayfair. Plus, 100 runners up will win a custom made Reiss silk pocket square that has been designed exclusively for Times+.

For your chance to win, enter the competition here