The leader of the Rat Pack, the chairman of the board, Il Padrone – Mr Frank Sinatra was not only the most successful singer of his generation, he was, and remains, an undisputed style icon. Why else would Jay-Z in “Empire State of Mind” benchmark himself by proclaiming, “I’m the new Sinatra”?

The fact that Mr Sinatra’s style still resonates globally today makes him an easy choice to launch our Very MR PORTER fall/ winter 2014 campaign. The tagline for the campaign was a bit of shorthand we had been using around the office for some time. We use it to describe a person or moment that is cool, elegant and fun-loving. To us Very MR PORTER doesn’t apply to one specific type of guy (or style of dressing). Like Jay-Z’s New York, being Very MR PORTER is a state of mind.

Once we settled on Mr Sinatra as an icon (and stuck one of our shopping bags under his arm), we began debating such burning questions as: if he were alive today, would he shop Rodeo Drive or Jermyn Street? What items would be in that bag? What would he make of Tinder? To find the answers, we turned to the definitive research — Mr Gay Talese’s landmark Esquire story_, Mr James Kaplan’s magisterial biography Frank: The Voice and Mr Bill Zehme’s _The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’. What follows are the elements of Mr Sinatra’s iconic style.

Mr Sinatra’s millinery was made expensively and often by Cavanagh – felts of black and grey for winter; pastel-banded straws for summer.

“He just put it on,” said his elder daughter, Ms Nancy Sinatra. “It was like an extension of him. The funny thing is, he wore them as a response to his receding hairline; it was just an easier way of dealing with it in public. He didn’t realise what a tumult it would start.”

Mr Sinatra had always been meticulous about how he dressed. As a boy on the back streets of Hoboken, New Jersey, his nickname was “Slacksey” due to the number of pairs of trousers he owned. “My mother bought me my first suit when I was 13 or 14,” he would say. “Later I got a job at the Jersey Observer and I used the money to buy clothes.” By the 1960s he reportedly had more than 150 suits. Beverly Hills tailor Mr Sy Devore was the official outfitter of the Rat Pack but later the chairman of the board would source his clothes from London’s Mayfair – suits from Dunhill, shirts from Turnbull & Asser, shoes from John Lobb.

“He was, as usual, immaculately dressed,” wrote Mr Talese in Esquire in 1966. “He wore an Oxford-grey suit with a vest, a suit conservatively cut on the outside but trimmed with flamboyant silk within; his shoes, British, seemed to be shined even on the bottom of the soles.” The shoes were often especially made with a built-up heel as without them he was only 5’7” or 5’8” (sources vary).

Though the black and white photography of his heyday doesn’t show it, Ol’ Blue Eyes loved to wear colour – but only during the day. Pink, lavender, lilac and especially orange. His numerous homes, offices, cars and private jet interiors were bedecked in orange hues. His signature flourish was an orange pocket square.

After dark it was a different matter. He never wore brown at night and was offended by those who did, often publically upbraiding them. He didn’t like the slovenly way in which younger men were beginning to dress. “I don’t want anybody in here without coats and ties,” he once snapped after an altercation with a casually dressed patron in his club, a telling anecdote revealed in Mr Talese’s profile.

Like many performers of his era, Mr Sinatra spent more time in black tie than most and had specific opinions about the cut and showing some linen. Or as he put it, “For me, a tuxedo is a way of life… My basic rules are to have shirt cuffs extended half an inch from the jacket sleeve. Trousers should break just above the shoe. Try not to sit down, because it wrinkles the pants. If you have to sit, don’t cross your legs. Pocket handkerchiefs are optional, but I always wear one, usually orange.”

Mr Sinatra was a stickler for precision and detail. “I was always fascinated by the pockets,” said his younger daughter Ms Tina Sinatra. “Everything had its own little home, neat and tidy. The white linen handkerchief on the inside pocket. The little mints. The individually folded tissues on the outer left – he didn’t grab a bunch; he separated each one. A single key on a fob.” And of course the money clip. He never carried credit cards. He didn’t believe in them.

“He had a place for everything on top of the dresser. He didn’t reach into his pockets and bring out handfuls of stuff and just put it down. He organised it in his little valet tray so that when he went to get dressed he didn’t have to worry about finding something. Everything was there.”

He didn’t over-complicate his wardrobe. “His closets were always rather small, even by today’s standards,” continued Ms Sinatra. “He was always going through them and organising and cleaning out and weeding out and giving away. He never had too many of any one thing, just the right amount.”

“It’s called ‘anal retentive’,” added Ms Sinatra. “I remember the closets the most. I would marvel at the way things were hung together in categories. Sweaters were folded on shelves; the hats were perched in rows up on the highest shelf; shoes with shoetrees lined the floor. Everything smelled like him. He had a scent and a style and an order to his life always.”

That scent was lavender: Yardley’s English Lavender until the Spanish cologne Agua Lavanda Puig later became his signature.

Mr Sinatra had a near-obsessive personal grooming routine. He took two showers a day, sometimes more. “Frank was the cleanest man I ever knew, forever changing his clothes and underwear, always showering and washing,” wrote the actress Ms Ava Gardner, his second wife. “If I’d caught him washing the soap, it wouldn’t have surprised me.”

His teeth were white, his fingernails were always impeccable and he was fastidious about not having a hair out of place, even if it wasn’t his: he famously wore toupees, though made no great secret of this.

But Mr Sinatra’s vanity had its limits. He believed a man should never hide his scars. He had his from birth, having been clumsily extricated from his mother with forceps during a near-fatal delivery that left him permanently marked on the left side of his neck. “People have suggested to me I ought to hide those scars, but no,” he would say. “They’re there, and that’s that. Why bother?” That said, he preferred to be photographed from the right side.

When the ways that men and women interacted changed, Mr Sinatra didn’t bend with the times. “I notice today that good manners – like standing up when a woman enters the room, helping a woman on with her coat, letting her enter an elevator first, taking her arm to cross the street – are sometimes considered unnecessary or a throwback,” he said. “These are habits I could never break, nor would I want to. I realise today a lot more women are taking care of themselves than in the past. But no woman is offended by politeness.” Manners extended to how you interacted with former lovers and wives. “Try to remain friends if you can.”

He smoked, as most people in Hollywood did back then, which helped his voice develop its rich baritone, though it was said he scarcely inhaled and rarely did he take more than four drags before extinguishing. After Lucky Strikes and Chesterfields, Mr Sinatra settled on Camels as his brand of choice, always unfiltered. “He liked to keep them loose from the pack in his right coat pocket,” records author Mr Zehme in his bestselling book The Way You Wear Your Hat. “The little gold Dunhill lighter was inside the right change pocket. Ever quick to light any woman’s cigarette, he opened the flame silently beneath the tip. The movement was fluid, almost unnoticeable, a lost art.”

Though he was notoriously impatient, Mr Sinatra was famed for his generosity and warmth towards those in his inner circle. The Hollywood actress Ms Rosalind Russell described him as “a knitter-together of people, a constant plate-filler and glass-replenisher”.

He had a remarkable memory for first names and enjoyed entertaining at his home in Palm Springs. “He always remembered what you drank,” said entertainer Mr Ed McMahon, a frequent houseguest. “He’d meet a person once and know that she liked white wine, that he liked Martinis and that someone else drank Manhattans. I could never get over that. With all the things in his life he had to remember, that he could remember everybody’s drink!”

Il Padrone’s own drink of choice was easy to remember. He didn’t choose any exotic booze. “I’m for anything that gets you through the night, be it prayer, tranquillizers or a bottle of Jack Daniel’s,” he used to say. He invariably opted for the latter: two fingers, with three to four ice cubes, in a traditional rocks glass.

His whiskey would be brought to him the moment he sat down – he didn’t need to order ­– and he’d let it settle before taking a sip. As with every pursuit, drinking had its own precise ritual: he drank right-handed, cupping the glass from below, preferably with a linen cocktail napkin.

In the wee small hours, you might have found him enjoying his favourite drink, Jack Daniel’s, although he rarely lost control. And as an artist he was never one to rest on his laurels. Or as he once said, “Never ignore an inner voice that tells you something could be better – even when other people tell you it’s OK.”