Frank Sinatra - Gentlemen of Style

Frank Sinatra – Gentleman of Style

Frank Sinatra. A name that everyone knows. A legend. An icon.

Sinatra was known for his music, his style and his behavior. Few men come with such a storied life. One of success, despair and secrecy. In this article we discuss on all those aspects and highlight the traits that can help you to advance your own style.

Sinatra’s Life

Born on December 12, 1915 in Hoboken, New Jersey, Francis Albert Sinatra was the son of Antonino Martino Sinatra, a lightweight boxer who fought under the name Marty O’Brien and worked as a Captain with the local fire department, and his mother, Natalina Garaventa who everyone called Dolly. She was influential in their neighborhood and local Democratic Party circles. For a career she operated an illegal abortion clinic and actually ended up being arrested for it multiple times. Despite this, she was known as an active mother who took pride in being able to provide for her son and his expensive taste in clothes. Even during the Great Depression is wasn’t uncommon for her to give Frank money to go out with his friends or for new clothes.

Frank Sinatra was a tough kid, noted for being quite rambunctious and a neighborhood hooligan. He never graduated high school as he was expelled due to his behavior and was arrested in 1938 for adultery and seduction. Working as a delivery boy for the Observer and then a riveter at a local shipyard, Sinatra had other plans. He was fascinated with music and knew his voice was good enough to carry him in a career. He spent all his free time listening to big band and jazz music. At the tender age of just eight he already began busking for tips by standing on top of the bar at a nightclub each night. By the time he was a teenager he was already starting to sing professionally.

By 1935, Sinatra had joined a local group called the Three Flashes. They changed their name to the Hoboken Four and began taking gigs on a local level. Somewhere along the line they caught the ear of Edward Bowes who hosted the show Major Bowes Amateur Hour. They were so successful on the show that they managed to amass over 40,000 votes which won them first prize. Similar to American Idol, the prize was a six month contract to perform on stage and radio across the continental United States. Within just a year, Sinatra decided to leave the group and returned home to work as a singing waiter at the Rustic Cabin in New Jersey. Four years later, Sinatra decided to make a demo of a song called “Our Love” with the Frank Mane Band.

By 1943, Sinatra was signed with Columbia Records as a solo artist. He was immediately successful and despite the musicians strike, he managed to amass a huge following by playing on the radio and on stage for his fans. Since his fan base was growing at such an alarming rate, Columbia wanted to record him as soon as possible. They hired Alec Wilder as the conductor for several sessions with a band called the Bobby Tucker Singers. The album was so successful that seven of the nine songs immediately made the best selling list.

Relaxed Sinatra with pleated trousers, dark hat and belt

Relaxed Sinatra with pleated trousers, dark hat and belt

When the draft hit, Sinatra never made it into the military on account that he had a perforated eardrum, but also that he was considered inadmissible due to psychiatric reasons. Throughout much of his life Sinatra had to contend with allegations that he bought his exemption through bribery. An investigation was launched by the FBI but no evidence was found to suggest it beyond a reasonable doubt.

Despite not serving, Sinatra did travel overseas with the USO tour to perform for troops. As legend has it, Sinatra demanded he be flown privately but Bing Crosby, a friend and confidant at the time suggested he not make demands. In the end, Sinatra went over to perform without any special treatment.


FILE PHOTO: An undated promotional photo of singer, actor and entertainer Frank Sinatra. (photo by Newsmakers)

Throughout his career, and his life, Sinatra was often viewed by others as being very peculiar or neurotic. Despite this, he was immensely talented, both as a singer as well as an actor.

Frank frequently worked with the Andrews Sisters and appeared as a special guest on a rare episode of their ABC Eight-To-The-Bar Ranch series. It was official; Frank Sinatra would no longer just be viewed as a very talented singer, but also an actor.

By 1945, Frank co-starred with Gene Kelly in the hit film Anchors Away. Later that year, he won an Academy Award for his work in The House I Live In which was directed by Mervyn LeRoy. The film won the award for showcasing tolerance and racial equality. In addition, he was given a Golden Globe for promoting good will. Sinatra was a household name and it was time to release his first album. The Voice of Frank Sinatra was released to the public in 1946 and followed by the debut of his radio show. He continued to gain popularity and fame, making him one of the world’s most famous singers of the time. However, by 1948 his popularity began to dwindle and he fell in the ranks of the most popular singers to number four. Worried his career was tanking, Sinatra signed on for the 1949 flick Take Me Out To The Ball Game again co-starring with Gene Kelly. It was a success and the duo teamed up again for On The Town.

Frank Sinatra with Oscar in Color

Frank Sinatra with Oscar in Color

By the end of the year, Lucky Strike cigarettes had taken notice of Sinatra and offered him a radio series called “Light Up Time”. The show was a flop however and only lasted less then a year. With the highs and lows of the recent years playing havoc on Sinatra’s wellbeing, he decided to take an absence from show business. In what easily could have been the end of a musicians career, Sinatra proved to be missed and returned to the stage in Connecticut on January 12, 1950. Despite the show being a success, Sinatra was aging and was no longer as popular with the teenage crowd that once lined up to see him perform. In September of 1951, Sinatra left for Las Vegas and debuted at the Desert Inn before becoming one of the most prominent entertainers to ever play the Las Vegas strip.

Unfortunately, this success was not expected and Columbia records decided to drop Sinatra as an artist. He was viewed as to arrogant and brash and many people didn’t enjoy working with him. For the next year, Sinatra played Vegas independently before starring in the 1953 blockbuster From Here to Eternity. After winning the Academy Award for Best Supporting Actor for his role in the film, his career rocketed back to the levels of success he once previously enjoyed. Despite the recent decline, Sinatra quickly became the top singer in the world once again.

Continuing to act on television, in film and perform as a singer, he signed with Capitol Records in 1953 where they gave him the opportunity to move into a jazzier genre of swing music.

He began receiving numerous awards including song of the year for Young at Heart from Billboard as well as Top Male Vocalist and Album of the Year for his second Capitol album Swing Easy.

He was a critical and financial success but was beginning to get beat out of the water by rock and roll, a genre he despised. He continued to stick with his love of swing and jazz and managed to get his 1959 song High Hopes on the Hot 100 for 17 weeks, a feat none of his previous songs managed to accomplish.

A tough man to impress, Sinatra grew to dislike his handlers at Capitol Records and decided to form his own label that he called Reprise Records. It was an instant success with the first album Ring-a-Ding-Ding! peaking at number four on Billboard and number eight in the United Kingdom.

Despite his public bashing and hatred of rock and roll, in an effort to maintain his viability in the industry, Sinatra did record Elvis Presley’s hit song Love Me Tender as well as songs for the Beatles, Paul Simon and Joni Mitchell.

As he continued in the movies, he also worked the Las Vegas strip with the Rat Pack, a group of singers led by him who worked together casually in films and concerts. Comprised of Sinatra, Dean Martin, Sammy Davis, Jr., Joey Bishop and Peter Lawford, the Rat Pack became the group that Sinatra is probably best known for performing with today. They worked on pictures such as Ocean’s 11, Sergeants 3 and Robin and the 7 Hoods. Despite Sinatra being difficult to work with and moody, the group stuck with him. Even when he replaced Sammy Davis Jr with Steve McQueen in Never So Few and Peter Lawford with Bing Crosby in Robin and the 7 Hoods due to personal grudges they still stuck by him, not taking it too personal but realizing he had his own internal demons to contend with.

The sixties were very successful for Sinatra with numerous songs released that hit the billboards as well as a number of hit blockbusters including The Manchurian Candidate which has been considered one of the greatest political thrillers ever made. With that he released a few big albums which gained international attention. He was about as big as they got in the music industry and he knew it, which is why he opted to retire when the 1970s came around. On June 13, 1971 the 55 year old Frank Sinatra, announced during a benefit concert in Hollywood that he would be retiring after what was considered one of the greatest musical careers in history that spanned 36 years.

Whether a PR stunt or not, retirement didn’t last for Sinatra and in 1973 he released a television special and album titled “Ol’ Blue Eyes Is Back”. It was a massive success and jump-started a new career for the mad man of Vegas.

In January of 1974, Sinatra went back to the strip and, despite vowing to never perform there again, took the stage at Caesars Palace, even after Sanford Waterman, the manager of the hotel, pulled a gun on him during an argument in 1970.

The remainder of the seventies and eighties proved mediocre success for Sinatra who was aging and no longer in touch with the younger fan base he once had. Despite this, he remained popular in comparison to other artists of his generation.

Throughout much of Sinatra’s life he had faced many demons. He suffered from bouts of depression and admitted to having manic depression. He was difficult to work with and to be close to, constantly needing to be away from the scene but not too far away that he’d lose touch.

A father to three children and a husband to four wives, Sinatra was married first to Nancy Barbato with whom he had his children. Following their divorce, he married Ava Gardner, Mia Farrow and finally Barbara Marx. Frank wasn’t a stranger to controversy and for many years was under the watchful eye of the FBI for his alleged connection to organized crime in New York and Las Vegas. In fact, the entire secret file on Sinatra was released to media in 1998 in response to Freedom of Information Act requests and it showed significant and consistent surveillance by the FBI for nearly five decades starting in the 1940s. The docket spoke of his friendship with John F. Kennedy, his political views and alleged ties to the Mafia. They even included proof of his extramarital affairs with prostitutes and dancers, as well as documents pertaining to his relationships with Marilyn Monroe, Dean Martin and other celebrities of the era.

Sinatra in black tie with signet Ring

Sinatra in black tie with signet Ring

There is little doubt that Sinatra was a big player in Vegas and knew everybody good and bad. He was feared, loved, hated and stalked due to his unusual behaviors, exquisite sense of style and alluring voice.

He was heavily involved in charity and politics and remained that way until suffering from a heart attack in February of 1997. Sinatra’s health quickly deteriorated and he was regularly hospitalized until his death on May 14, 1998 when he suffered another, this time fatal, heart attack. He passed away at Cedar Sinai Hospital in Los Angeles with his wife Barbara at his side.

Sinatra lived his life, his way. He will forever go down in history as a legend. The musician, the actor, the man. There is no one like Frank Sinatra.

Sinatra’s Style by Sven Raphael Schneier

Many people admire Sinatra for his style but what exactly were the hallmarks of his style? In the following we will break it down in clothes and general aspects of what made Sinatra the man he was.

Bill Zehme, author of the ode to Sinatra – The Way You Wear Your Hat – was obviously impressed by Sinatra’s style when he wrote: “Arguably, no man ever lived life more broadly or confidently or stylishly than Frank Sinatra,”
If you want to be as stylish as Sinatra, you did set your goals rather high, but it is achievable. Of course, imitating osomene’s style doesn’t work but you can understand the basic principals and draw your own conclusions.

Sinatra & Clothes

Just like Cary Grant, Frank Sinatra once expressed a number of things that he considered to be essential, so here we go:

“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.”

Sinatra’s 15 Rules of Style

  1. The hat was undeniably one of his hallmarks. It takes two hands to put on a hat the right way: Back brim curled up, front tugged down to a couple of inches above the right brow.
  2. No brown, white, grey or blue after the sun goes down unless it’s midnight blue. After dark, men should wear black.
  3. Wear conservative silk ties
  4. Cuff links always. But leave the fancy jewelry to Sammy.
  5. When dressing formally, a vest is better than a cummerbund.
  6. Don’t wear a tuxedo on Sunday.
  7. Having messy closets is like putting on clean clothes over dirty underwear.
  8. The shower is a great place to steam out the wrinkles in your dinner jacket.
  9. Orange is the happiest color.
  10. Don’t hide your scars. They make you who you are.
  11. When it comes to pockets, everything should have its own place.
  12. Wear a pocket square that is perfectly folded.
  13. Shine your shoes.
  14. Trim. Buff. Clean. But always make it look easy & nonchalant.
  15. Take your hand off the suit.

Sinatra’s Behavior & What it means for you

It is difficult to capture the essence of Sinatra’s Style in one sentence, but here you find a couple of pointers of what it means.

  1. Have an attitude & don’t be afraid of being your edgy self. It swings easily, but there’s a bite there. It seems casual and effortless, but it’s commanding. In Sinatra Style, ease and authority go hand-in-hand.
  2. It’s swagger but not flash. Swagger is not ostentatious or showy. Swagger knows it’s damn good, and it knows you know it. Swagger is confidence, even cockiness, but never showy.
  3. Be generous. Take care of the little guy,  and don’t worry about money. Of course, it’s easy not to care about money if you have it, but Sinatra had style even in his down days.
  4. Show some loyalty. Sinatra loved to be around people though he was also lost and lonely. Hell, nobody is better at expressing that feeling that comes when you’re alone at the end of the bar at closing time in the wee small hours, and you know she’s not coming back. It carries that feeling deep inside, always. Maybe that’s why it’d rather be at a table of friends in that same bar, ordering up another round and holding off the night until dawn.
  5. Leave big tips. Sinatra was big tipper, a real big one, but a quiet one. If the valet walks away with a “Benjamin” that’s between you and the valet, no-one else.
  6. Help the one’s in need, but don’t brag about it or advertise it afterwards.
  7. Wear well fitting clothes.
  8. Be passionate – real passionate . Sinatra wouldn’t hold back from a fight when it was about something he was passionate about. Maybe he could have stepped back at times, but that’s not the way it works. No need to apologize. Leave it, and move on.
  9. Create your own style. Sinatra lived by a code—his own code, not anybody else’s code and if you want to be as stylish as him, you have to create your own code.
  10. Always be clean, never sloppy even if you enjoy  a drink too much every once in a while.

Sinatra’s Beliefs

  1. Loosen up. Swing, man.
  2. Keep moving. Do it, do it right, and move on.
  3. Don’t despair. Just because you’ve been up and down in life more than a roller coaster on the Fourth of July doesn’t mean that you won’t get another shot at your dreams.
  4. Sleep is overrated. Warren Zevon wasn’t a Sinatra guy, exactly, but that line of his, “I’ll sleep when I’m dead,” does have a ring to it.
  5. Timing is essential when you’re singing a song. But in real life there are times you just have to get there when you get there.
  6. Smoking is stupid. Sometimes you do it anyway.
  7. If it’s worth saying, Cole Porter probably said it in a song. Or Rodgers and Hart. Or Sammy Cahn and Jimmy Van Heusen.
  8. Roll with the punches. Wear a clown face if the situation calls for it. Defy the system. You’ll scare the uptight, locked-in people, but so what?
  9. If you have talent, you must embrace it, nurture it, and share it, or it’ll be taken away as fast as it was loaned to you.
  10. Don’t stress. The overly concerned and sincere drive themselves crazy. On the other hand, it’s okay to be a little crazy. In fact, it’s essential.
Frank Sinatra

Frank Sinatra

Article Name
Frank Sinatra - Gentleman of Style
Learn all about the Life Story of Frank Sinatra, his Believes, his Style and what you can learn from him.
14 replies
  1. Dr. Olaf S. van Hees says:

    An article that gives good information.
    But, my dear Sven, although I mostly agree with your articles, I thoroughly disagree with you on Frank Sinatra being a gentleman. He certainly was NOT, according to the true gentleman´s standards. Too swingy, too slick, too sticky, too big spender, too showy, etc.
    But perhaps I am too Calvinistic (although I studied at the Jesuits).

  2. Yoshi says:

    He sounds like an egotistical and narcissistic individual, surely not qualities I would associate with a true gentlemen. The way he used women is especially distasteful, to say the least.

  3. N.R says:

    I got into Sinatra’s music by a happy accident about four years ago, after I was given a pile of CDs my father no longer wanted. I was in a horrid point of my life where I’d been trying to bounce back after a nearly successful suicide attempt, and dumb as it may sound Sinatra was a huge part of what pulled me back together. Those last few, swelling lines of “My Way” became my mantra and for that I’ll always love the man, neurosis and mob ties or not.

  4. Mark Hewitt says:

    I am a huge fan of Frank Sinatra and seen him perform many times . Some of the Tuxedos he wore were beautifully put together ; mind you he could look good in a potato sack .

    The edge that he had over a lot of men was the thing money cant buy . You either got it or you ain’t . It is called talent mixed with class and that is what makes style . I don’t care what shop you go to ; or what they sell you can’t buy it , you can only try and emulate it .

  5. Phil Maniatty says:

    No one told a story with a song as well as Sinatra. I am surprised, however, that you didn’t mention Harry James or Tommy Dorsey. They were key influences in Sinatra’s development as a singer.

  6. Mark E. Seitelman says:

    As for Sinatra and his love of clothing:

    As a young teen he had the nickname of “Slacksie O’Brien” based upon his many clothes. The O’Brien came from his father’s bar which was named Marty O’Brien. His father, Martin Sinatra, gave his bar an Irish name because the Irish were more established and accepted than the “newcomers” from Italy.

    Sinatra patronized Savile Row. I believe that he purchased suits from Cyril Castle.

    Sinatra had a “fling” with J. Press! Richard Press recalls Sinatra’s brief time as a customer here: A former J. Press salesman told me that, believe it or not, J. Press used to stock Brioni suits at that time. Sinatra probably bought Brioni’s.

    Last, on a related note, Sinatra liked the color orange which he categorized as a “happy color.” He used orange in his home decor.

    Mark E. Seitelman

    Sinatra loved the

  7. Frank says:

    Frank Sinatra had a very interesting life indeed. 🙂

    Sinatra wore the style of the day, but with class. In the many photos I’ve seen of him he looks comfortable in them.

    He didn’t like a sloppy atmosphere, as stated in an article, “Frank Sinatra Has A Cold”, the writer states, “Sinatra was in a club one night and looked around the room, and said, “These people should be wearing suits and ties.””

    I read in one of Cary Grant’s biographies, that after Grant passed away, Sinatra received a number of cuff links from Grant’s widow.

    In Martin Greenfield’s current book, “Measure Of A Man” he states that he remembers when Frank, Sammy, and the gang were GGG customers. And that some of the tuxedos were made without pockets. They’ed have flaps, but that was it, they’d be used for TV and stage production and were considered uniforms for tax purposes.

  8. Brett Vaughan says:

    I have to agree wholeheartedly with ol blue eyes, his style is engaging, timeless and classic. There’s no going wrong dressing like Sinatra, even going so far as to flip that coin.

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