Frank Sinatra was an American singer and actor, born in 1915. Francis Albert Sinatra (his full name) was the son of Antonino Martino Sinatra, a lightweight boxer who worked as a Captain with the local fire department, and Natalina Garaventa who was in charge of an illegal abortion clinic. He was a neighborhood hooligan and has never graduated from the high school.

Sinatra was fascinated with music and knew his voice was excellent to make a career from it. He started his singing career as a teenager.

Frank Sinatra’s Style

Bill Zehme is the author of a book about Sinatra called The Way You Wear Your Hat. The book shows his fascination with Sinatra and admiration for both his work and personality. Zehme wrote:

“Arguably, no man ever lived life more broadly or confidently or stylishly than Frank Sinatra.”

When actually asked about his own style, Frank Sinatra used to express a number of things that he considered to be essential:

“For me, a tuxedo is a way of life. When an invitation says black tie optional, it is always safer to wear black tie. 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, since orange is my favorite color. Shine your Mary Janes on the underside of a couch cushion.”

The rules of Sinatra’s style

Gathering this info from Bill Zehme’s book, we have put these rules in an order for anyone, who wants to copy Sinatra’s style, to actually follow them. These are the steps for you to follow if you want to have Sinatra’s style.

His way of putting on a hat was this: Back brim curled up, front tugged down to a couple of inches above the right brow.
Never wear a tuxedo on Sunday.
Don’t wear brown, white, gray, or blue after the sunset except for midnight blue. When it is night, men should always wear black.
Always put cufflinks, but no fancy jewelry!
For him, the happiest color was orange.
When choosing ties, always wear conservative silk ones.
A vest is better than a cummerbund when dressing formally.
In pockets, everything should have its own place.
Messy closets are like putting on clean clothes over dirty underwear.
Always shine your shoes!
The great place to steam out the wrinkles in your dinner jacket is in the shower.
The pocket square should always be perfectly folded.
Your scars make you who you are, don’t hide them!
Always tend to look easy and nonchalant, and frequently trim, buff and clean.

Sinatra’s gentleman behavior

On the other hand, if you want to have both – Sinatra’s style and his demeanor, then here are his attitudes to be followed.

Always wear well-fitting clothes.
Always keep your attitude and don’t be afraid of being your grumpy self.
Be a swagger. Swagger is confident, even cocky, but never showy.
Always leave big tips.
Be generous and don’t worry about the money.
Be a loyal friend.
Help people in need, but don’t brag about it afterward.
Always be clean, never sloppy.
Be really passionate about the things you cherish the most.
Have your own style as your own fashion code.

Sinatra’s beliefs

He had some simple beliefs which can be accepted by anyone. So, it is not so difficult to be a stylish gentleman, right? See those beliefs and decide for yourself.

Loosen up, don’t be strict and uptight.
Keep moving.
Don’t despair.
Sleep is overrated.
Timing is essential when you’re singing a song. As opposed to the real life when there are times you just have to get somewhere whenever it happens. No haste.
Smoking is an unwise habit.
If something is worth saying, then there are songs already made about it by Cole Porter, or Rodgers and Hart, or Sammy Cahn and Jimmy Van Heusen.
Roll with the punches.
Wear a clown face if necessary.
Defy the system.
If you have some talents, you must embrace and nurture them. Otherwise, they will be taken away as fast as they were loaned to you.
Don’t get stressed out.
It’s essential to be a little crazy.