1. Go big or go home
Sinatra's penchant for a large glass of bourbon was matched only by his love of quality tailoring. In fact, he was rarely pictured out of a blazer and shirt, which proves there's scarcely an occasion when dressing smart isn't the way to go.
2. The devil is in the detail
Never one to be outdone in the style stakes, Sinatra always made subtle additions to his outfit, which marked him out as sartorial power-player. Narrow ties, crisp pocket squares and gold cuff links are just a few of the ways he chose to dial things up a notch.
3. Always tip
Nothing injects a fat shot of attitude into an outfit quite like a tipped fedora. But if you're going to buy a hat, spend some money and make sure it fits. Plastic fancy dress hats just won't do.
4. If in doubt, wear black
After dark, Sinatra was rarely seen in anything but a black suit and shoes with a white shirt. All over black, with small punches of colour, continues to be a firm fallback for anyone unsure of what looks good on a night out.
5. Dress like your mates
Sinatra was the leader of the Rat Pack. And as groups of mates go, he, Dean Martin, Sammy Davis junior and co. couldn't have looked any sharper. This proves that when in doubt, look to what your friends are wearing for inspiration, then wear it better than them.