How to dress like Frank Sinatra

Nicknamed "'Ol Blue eyes", "Sultan of Swoon", "Swoonatra", and simply "The Voice", few celebrities could rival the influence and sway of Frank Sinatra even today. A legendary singer, actor, and fashion icon, Sinatra had not only made history with his music but also had set standards in fashion that will be deemed as classic rules for years to come.

(Frank Sinatra, possibly in the late 20s as a young child)

Born Francis Albert Sinatra on Dec 12 1915 to Italian immigrants, Frank Sinatra's father was a professional boxer and later a firefighter while his mother was a midwife influential within his home town of Hoboken New Jersey. He had interest in big band and jazz music at a very early age and had used his singing voice to get through his early days earning minor pay for amateur gigs.

(Frank Sinatra, far right, with the Hoboken 4 and with Major Bowes in the background)

In 1935 Started his professional singing career by entering a local band called the 3 flashes turned the Hoboken Four when he joined. The group found success winning a contest on the Major Bowes Amateur Hour show where the first prize was a six-month contract to perform on stage and radio across the United States.

(Frank Sinatra, right, performing with Harry James (left) and the rest of his band, 1939)

In 1939 Frank Sinatra joined the Harry James band and released his first commercial record "From the bottom of my heart" that year, unfortunately this and other records had weak sales that year

(Frank Sinatra (on top row, right most corner) with the Tommy Dorsey band, with Tommy Dorsey holding his trade mark trombone and glasses, 1940)

(Frank Sinatra, close up of previous photo)

In November 1939 Frank left the band to join The Tommy Dorsey band and made several appearances with them over the next years where he found his first major successes in his career starting with the song "Polka Dots and Moonbeams" and "Imagination" which would make his first top ten hits. His stay with the band influenced him the most because of the band's founder Tommy Dorsey, who took him under his wing for guidance and tutelage, and also allowed him to record a few solo records. His successes in his solo records convinced that he needed to continue solo, which he did in late 1942, leaving the band to make a name for himself

Being a perfectionist like Frank and just as mercurial, Tommy Dorsey had many similarities with Frank Sinatra, and it was only natural that Sinatra learned all he could from his tutor.
In addition to advanced music techniques that helped him define his iconic singing style, Frank Sinatra had also adopted Dorsey's fashion style and it is this style that had stayed with him for many years to come and became iconic as he put his spin on it.

(Frank Sinatra (left) in a conversation with drummer Buddy Rich (centre) and his mentor Tommy Dorsey (right), 1941)

Here we share some of the key pointers that mark Frank Sinatra's fashion style

(Frank Sinatra in his youth, in a police mug shot, arrested for seduction and adultery - he was only 23 years old)

When he was born, he was scarred and had a perforated right ear drum because he had to be delivered with the aid of forceps. Frank had accumulated more scars throughout his life such as one on his neck from an operation on his mastoid bone as a child and cystic acne during his adolescent. He will eventually be 5 ft 7 in (170 cm) and 65 kgs as an adult

Despite these physical shortcomings, Frank was always a fighter because of his upbringing and always had a zeal for life and a perfectionist's tenacity that often landed him in trouble and at odds with others.

(Frank Sinatra, playing the piano while wearing a navy blue suit with notch lapelled jacket, also wearing satin blue and silver stripped tie, white pocket square and his trade mark fedora, for a television production of ‘’Our Town’’ in 1955)

Frank Sinatra's suits always a little oversized in keeping with the fashion at the time - but length wise they were all meticulously tailored - shirt cuff should extend half an inch from the jacket sleeve, trousers should break just above the shoe. In this manner, he was able to exude an air of effortless elegance while effortlessly being able to dress down anytime he wanted. During his later hey days, most his suits were made by Sy Devore.

(Frank Sinatra, with dark grey barleycorn patterned high waist pants, knit button suspenders, gold cuff links and untied black bow tie)

In keeping with norms, his pants are usually high-waisted, and it works well with Sinatra's whip thin frame since the proportions are guaranteed to look more elegant by emphasizing his already thin waist and gives an illusion of longer legs and therefore height.

(Frank Sinatra wearing a dark flannel three piece suit with a single-breasted, notch lapelled jacket, and a low cut five-button waistcoat with a notched bottom. Also wearing double reverse-pleated trousers, dark patterned silk pocket square, collar pin, neck tie with a repeating series of light circles against a dark ground. Topped with a dark straw short-brimmed trilby hat with a wide white puggaree ribbon. Photographed at Heathrow Airport, mid-1961)

Concerning his suit colour, Sinatra believed that men should wear dark suits (except for dark brown) at night, but would often go with gray and blue suits as well as plaid and pinstripe ones during the day. Also when in doubt, go for black tie except on Sundays. It is this meticulous adherence to always dressing up to the nines at any occasion that exposed and cemented Sinatra's status as a fashion icon to the world.

(Frank Sinatra, posing at phone, wearing grey flannel pants with white pin stripes, dark button suspenders, dark satin tie with white polka dots, onyx set gold cufflinks and trilby hat cocked to one side, possibly about early 1942)

If Sinatra would choose a pattern on his suits, he would sometimes go for pinstripes with a polka dot tie - this way the pinstripes will give an illusion of height and the tie will emphasise his chest. The two patterns together are the simplest patterns on the sliding pattern scale

(Frank Sinatra, posing in studio wearing a white shirt with black polka dots, flap button pockets, and grey flannel pants, 1945)

As a matter of fact, Sinatra would sometimes wear polka dot shirts - it also works to again emphasize his chest, and it works either in a casual setting or a more formal setting

(Frank Sinatra, photographed with a sculpture of him made by Jo Davidson, wearing checked grey suit with navy blue knit tie, gold cufflinks, 1946)

Because of the proportions of the length of his sleeves, cuff links are essential in Sinatra's outfit, as Sinatra says,"You’ll need them if you’re wearing your jacket sleeves" and he preferred his in simple gold

(Frank Sinatra here wears a glenchecked grey overcoat, black suit, black tie with white polka dots and an orange waistcoat. Topped with a dark brown trilby hat. On the set of "Come Blow Your Horn", 1963)

While Sinatra could be seen in any number of ties in different patterns and colours, he always made an effort to include his favorite colour orange somewhere in his outfit because "orange is the happiest color." Usually it was in the form of an orange pocket square, crisply folded

(Frank Sinatra here wears a dark suit with a notch lapelled jacket, satin speckled dark neck tie, a lighter coloured trilby hat, and a pair of black patent leather derby shoes. Shown here during a capitol studio session 1957)

As for shoes, he usually wears black patent shoes, reserving brown shoes for informal or daytime wear, and Sinatra would go out of his own way to ensure his pair are always polished to some degree at any one time - he even once said “Shine your Mary Janes on the underside of a couch cushion”. Derby and patent slip-on shoes are his usual go tos.

(Frank Sinatra wearing a grey flannel suit with wide notch-lapelled jacket, gold lapel pin, royal blue satin skinny tie, and a grey fedora with a wide ivory silk hat band. Seen here in a studio session at Capitol Records, 1954)

Also he is rarely seen without his hat cocked to one side - it became one of his signature looks. During that time, hats are a quinessential item in men's fashion and it is a seperate art altogether finding a hat that suits you the best. However, most of Sinatra's hats are made by Cavanagh hats and he prefered fedoras since the wide brim works well with his head shape, and with the rakish tilt to one side, it looks positively devastating.