Here’s the Secret to Why Frank Sinatra Was So Stylish!

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With a career that spanned six decades in both singing and acting, Frank Sinatra was one of the biggest stars of the 20th century. Famed for his achievements on the stage and in front of the camera, and for his raucous personal life and escapades, especially as a member of the famous Rat Pack, Frank Sinatra left an indelible mark in the world.

While his talent as a singer and presence as an actor certainly helped solidify that reputation, we suspect a big part of Frank Sinatra’s appeal and staying power was his remarkable realization of Classic Style. It is for that reason that Sinatra is considered a Classic Style Icon and one of our Gentlemen of Style.

Photo of Bill Zehme

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

Bill Zehme

Today, we will examine exactly what made Sinatra so stylish by reviewing his remarkable life story, defining his style, explaining how his clothes and personality reflected it, and concluding with ways that you can utilize Sinatra’s techniques as part of your own personal on Classic Style.

Frank Sinatra’s Life and Career

Frank Sinatra’s Younger Years

Photo of Sinatra as a young boy
Even as a kid, Frank Sinatra was dapper!

The Sinatra Family

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.

Dolly 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, it wasn’t uncommon for her to give Frank money to go out with his friends or for new clothes.

A Rough-and-Tumble Childhood

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.

Frank Sinatra's mugshot
In 1938, Frank Sinatra was booked on charges of adultery and seduction. This charge was typically leveled against unmarried young men who engaged in sexual relationships with married women.

Although originally 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 starting to sing professionally.

The Start of Frank Sinatra’s Musical Career

The Hoboken Four

Photo of The Hoboken Four
The Hoboken Four, with Frank Sinatra at the far right, perform on the Major Bowes’ Amateur Hour, with Edward Bowes himself at the center. [Image Credit: Wikimedia]

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.

“Frank hung around us like we were gods or something. We took him along for one simple reason: Frankie-boy had a car. He used to chauffeur us around.”

Frank Tamburro

The Hoboken Four 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.

Sinatra Signs with Columbia Records

Photo of album cover

Frank Sinatra’s First Album

The Voice of Frank Sinatra

Issued in 1946, The Voice of Frank Sinatra was the singer’s debut studio album, released by Columbia Records. Notable tracks include “Somene to Watch Over Me,” “Try a Little Tenderness,” and “Why Shouldn’t I?”

By 1943, Sinatra was signed with Columbia Records as a solo artist. He was immediately successful, and despite the musician’s strike raging at the time, 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.

Avoiding the Draft and USO Tours

Photo of Frank Sinatra as young man
Frank Sinatra performing for American servicemen.

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.

Frank Sinatra Breaks into Film

Photo of Bing Crosby with the Andrews Sisters
Frank Sinatra’s early career was helped by his appearing alongside other famous singers of his day, like Bing Crosby and the Andrews Sisters. [Image Credit: Wikimedia]

During the 1940s, Frank Sinatra regularly sang with the Andrews Sisters, and he 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.

Still of Sinatra in an RKO feature
Early in his film career, Frank Sinatra was usually cast as a heart-throb character.

By 1945, Frank co-starred with Gene Kelly in the hit film Anchors Aweigh. 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, Sinatra was given a Golden Globe for promoting goodwill.

Film poster for Anchors Aweigh

“Well, what’s the good of having a life saved when you can’t have any fun with it?”

Frank Sinatra as Clarence Doolittle in Anchors Aweigh

By this time, 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 was 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.

Sinatra’s Transition to Las Vegas

Photo of Las Vegas in the 1960s
Fremont Street in Las Vegas during the 1960s. [Image Credit: Wikimedia]

By the end of 1949, 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 than a year. With the highs and lows of the recent years playing havoc on Sinatra’s well-being, he decided to take an absence from show business.

In what easily could have been the end of a musician’s 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 ever to play the Las Vegas Strip.

Sinatra Parts Ways with Columbia and Achieves New Fame

Unfortunately, this extracurricular success was not expected, and Columbia Records decided to drop Sinatra as an artist. He was viewed as too arrogant and too brash, and Columbia learned that other popular public figures found it difficult to work with Sinatra.

From Here to Eternity Film Poster

“Let’s go to a phone booth or something, huh? Where I will unveil a fifth of whiskey, I have hidden here under my loose, flowing sports shirt.”

Frank Sinatra as Angelo Maggio in From Here to Eternity

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.

Sinatra Signs with Capitol Records

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.

Album Cover In the Wee Small Hours

Frank Sinatra’s 9th Studio Album

In the Wee Small Hours

Inspired by his relationship with his second wife, Sinatra’s album In the Wee Small Hours was released in 1955 and featured favorites like “What Is This Thing Called Love,” “Young at Heart,” and the titular track.

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.

Sinatra 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.

Label Independence and the Rat Pack Years

Formation of Reprise Records

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 from the Beatles, Paul Simon, and Joni Mitchell.

Frank Sinatra and the Rat Pack

Photo of the Rat Pack
The five leading members of the Rat Pack, including Frank Sinatra. How many of these stylish gents do you recognize?

As he continued in the movies, Sinatra also worked the Las Vegas strip with the Rat Pack, a group of entertainers 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.

Photo of the Sinatra family

Frank Sinatra’s

Personal Life

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.

They made numerous pictures together, including Ocean’s 11, Sergeants Three, and Robin and the Seven 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, the Rat Pack still stuck by him, not taking it too personally but realizing he had his own internal demons to contend with.

Robin and the 7 Hoods in their stylish classic men's suit ensemble.
Sinatra, Bing Crosby, and Dean Martin appear together in a still from Robin and the Seven Hoods.

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. Sinatra also released several of his most successful albums, which gained him additional international attention.

Frank Sinatra Retires (For a Few Years)

Bowing Out at the Height of His Fame

At the dawn of the 1970s, Frank Sinatra was about as big as anyone could be in the music industry, and he knew it, which is why he opted to retire. 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.

Photo of Sinatra with John F Kennedy

The Controversial Life of Frank Sinatra

Sinatra 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 fact, the entire secret file on Sinatra was released to the media in 1998, 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.

Frank Sinatra Returns

Photo of Frank Sinatra as an older man
Frank Sinatra in Black Tie following his return from retirement.

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 madman of Vegas.

In January of 1974, Sinatra went back to the Strip and, despite vowing never to 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 Close of Frank Sinatra’s Career

“The Chairman of the Board” of Las Vegas

As he grew older, there was little doubt that Sinatra remained 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.

The Death of Frank Sinatra

Photo of Frank Sinatra grave
Frank Sinatra’s grave marker in Desert Memorial Park Cemetery, Cathedral City, California. [Image Credit: Wikimedia]

Sinatra 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.

Frank Sinatra’s Style FAQ

What is Frank Sinatra’s style?

Frank Sinatra’s personal style was firmly rooted in the Classic Style of the mid-20th century. He relied extensively on suits and sport coats, but also integrated more casual elements like knitwear. His color palette was largely conventional and neutral, although he often added bright, individual elements, especially in his favorite color, orange. In general, Sinatra relied on contrast between his clothing articles or the careful use of texture to differentiate between the elements of his ensembles.

Was Frank Sinatra’s style “Classic?”

Yes, it was. With his strong emphasis on the conventional rules of Classic Menswear, which he broke sparingly and always with particular stylistic intention, Sinatra embraced the general guidelines of Classic Style but was never afraid to inject his own personality and panache into his looks.

Did Frank Sinatra impact Classic Style?

Yes, he did. Thanks to his reliance on classic garments in traditional cuts, all made from quality materials, Sinatra became a Classic Style influencer in his own right, and his legacy has encouraged many people since to follow in his stylish footsteps. 

How did Frank Sinatra employ clothing as part of his personal style?

Sinatra intentionally utilized clothing that suited his personality and personal aesthetic. Most of his clothing articles were fairly conventional, and when he wore something bold, he emphasized it by keeping the rest of his look sedate. Sinatra also made liberal use of subtle ways to reflect his personality in his clothes. This included cocking his hat at a jaunty angle, rolling up his sleeves, wearing his tie loose or undone, and employing signature pieces. 

What clothing and accessories are most associated with Frank Sinatra?

Sinatra is closely associated with hats, primarily trilbys and fedoras. He also regularly wore both suits and sport coats, favoring contrasting combinations among the latter. For casual wear, Sinatra regularly wore knitwear, especially plush cardigans. Many of Sinatra’s garments and accessories were in his favorite, signature shade of orange. 

How can I dress to look more like Frank Sinatra?

The best way to emulate Sinatra’s style is to follow many of the basic rules of Classic menswear. Source quality garments, remember that fit is king, and rely on accessories to add vibrancy to your ensembles. You may want to add a jaunty, slouching refinement to your look by loosening your tie, undoing buttons, and generally embracing the casual sprezzatura look that Sinatra embodied. Finally, the judicious use of statement pieces, like a flattering hat, will also help you dress to impress like Sinatra did.

Why is Frank Sinatra associated with the color orange?

Sinatra once declared that orange was the “happiest color,” and that wearing it made him feel happy and confident. Therefore, whenever he could, he attempted to incorporate that shade into his ensembles, even if only as a small accessory like a pocket square.

Defining the Frank Sinatra Style

The Classic Look of a Mid-Century Menswear Influencer

Photo of Frank Sinatra ingray suit with hat
Frank Sinatra was one of the most influential style icons of the 20th century.

It is no exaggeration to say that Frank Sinatra was one of the foremost menswear influencers of his day, and with good reason.

From an overview perspective, Sinatra’s style was built upon a relatively neutral and unobtrusive color foundation augmented by occasional pops of unexpected color, texture, and pattern.

Essentially, most of the basic elements of a Classic ensemble are represented, but with one or two unique elements or pieces of flair for visual interest that were too marvelous for words.

How Frank Sinatra Employed Contrast

To add creativity and pop to his look, Sinatra relied on contrast to create memorable visual interest. He achieved this by utilizing the interplay of dark and light colors, solids and patterns or textures, and variations between sedate and bold garments and accessories.

Photo of Frank Sinatra dark suit with orange necktie

Contrasting

Dark and Light Colors

Photo of Frank Sinatra Striped Suit with Polka Dot Bow Tie

Contrasting

Patterns & Textures

Photo of Frank Sinatra Polka Dot Tie

Contrasting

The Bold & Sedate

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“My basic rules are to have shirt cuffs extended half an inch from the jacket sleeve. Trousers should break just above the shoe….Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favorite color.”

Frank Sinatra

How Frank Sinatra Carefully Employed Bold Elements

Still from Marriage on the Rocks
Frank Sinatra wears a bright orange cardigan in Marriage on the Rocks (1965)

To give conceptual weight to those moments when he did employ bold style elements, like unusual colors or loud accessories, Sinatra toned the remaining elements of his ensembles, relying on clean, simple lines to timelessly frame his look and texture to differentiate each element. This ensured that his outfits weren’t overwhelming, even when he wore vibrant colors like orange.

How Frank Sinatra Incorporated His Personality into His Style

After assembling the various elements that made up his Classic looks, Sinatra added a bit more personality by layering on a playful, tousled element, usually in the form of a cocked hat, loosened tie, or rolled-up sleeves.

But Sinatra never appeared shabby or unkempt when pulling off these flourishes, because he artfully arranged his look to appear whimsical while still keeping every element in place. Yes, he wore his tied loosened, but only after properly knotting it, tightening it, and then astutely loosening it for a casual but elegant look.

Essentially, Sinatra put in the work to make his style appear effortless and easy in a perfect example of sprezzatura. What else would you expect from a well-dressed Italian American?

Master sprezzatura, just like Frankie!

What You Can Conclude from Frank Sinatra’s Personal Style

Photo of Sinatra in orange cardigan
Frank Sinatra in his iconic orange cardigan, a color that he loved to wear.

In attempting to summarize Frank Sinatra’s style, we can say, generally, that he adopted and abided by Classic Style conventions, intentionally deviating only on select occasions that did not interrupt the cohesion of the rest of his ensemble. He always endeavored, however, to leave a personal mark on any look that he wore.

Photo of Frank Sinatra breaking a few black tie rules in his old age

Did Frank Sinatra have any

Style Slip-Ups?

While Frank Sinatra did occasionally embrace some trendier styling elements that broke with Classic conventions, particularly in his later years, n the whole he cleaved primarily to timeless style conventions, especially when compared with the more fashion-forward looks worn by fellow Rat Pack members Dean Martin and Sammy Davis, Jr.

How Frank Sinatra’s Clothing Made Him Stylish

Turning Classic Garments into Personal Statement Pieces

Photo of Frank Sinatra in brown sport coat with orange vest and bold silk tie
Every article in this picture is typical of Classic Style, but Frank Sinatra found a way to wear them that was all his own.

Having considered how Frank Sinatra styled himself generally, let us now consider individual clothing items that Sinatra stylishly wore. We will open with his signature pieces: essentially, generic Classic style items that Sinatra wore in such a way as to make them his own.

Frank Sinatra With Collar Pin

“Cock your hat – angles are attitudes”

Frank Sinatra

Garments Perfectly Employed By Frank Sinatra

Photo of Frank Sinatra dark suit cocked hat

Dress Hats

While less common today, dress hats were ubiquitous during most of Frank Sinatra’s career, so he made his headwear, usually a trilby or fedora, his own with by cocking it at a rakish angle. Wearing something worn by others in a way they don’t wear it is a great way to make any article into a statement piece.

Photo of Frank Sinatra in yellow pull over v neck sweater jumper

Knitwear

Sinatra seamlessly integrated knitwear into his more casual ensemble rather than relying on the leisure shirts or sport shirts popular during his day. This allowed Sinatra to cultivate a casual and sporty look without looking like everyone else.

Photo of Frank Sinatra in an orange sport shirt and sport coat

A Personal Color

Sinatra adopted a personal color to leave his mark on his looks in a subtle way. Adopting orange, a notoriously underutilized color in menswear, Sinatra employed it wherever he could in his ensembles while still being mindful of expected formality. He didn’t do this to be flashy or contrarian, however, but because he genuinely loved the color. When asked why, he said because “Orange is the happiest color”

Frank Sinatra 1959 "Come Dance With Me" Capitol Records © 1978 Sid Avery

“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.”

Frank Sinatra

Frank Sinatra Favored Form Over Flash

Although remembered as a flashy and dashing character, Frank Sinatra’s personal style actually favored form over flash, because, other than occasional pops for visual interest, he kept his wardrobe sedate with an obvious quality-over-quantity approach.

Focusing on his choices in neckwear and men’s jewelry, this aspect of Frank Sinatra’s style becomes apparent.

Collage of Frank Sinatra wearing Classic mens jewelry
Even when it became trendy for men to wear excessive, oversized jewelry, Frank Sinatra largely limited himself to Classic options like collar jewelry, cufflinks, and the occasional pinky ring.

Learn the secrets to properly wearing men’s jewelry!

Frank Sinatra Properly Cared For His Clothing

Photo of Frank Sinatra in dark suit with trench coat over his shoulder
Despite his casual attitude, Frank Sinatra was actually a stickler when it came to keeping his clothes pressed, neat, and tidy.

When it came to the care and keeping of his garments, Sinatra lavished his attention on every detail. Despite the jaunty way that he wore them, his shirts were always crisp, his suits were pressed, and his shoes were shined.

The laidback way that Sinatra sometimes wore his clothes wasn’t an attempt to cut corners or be lazy: it was a genuine expression of his laissez-faire attitude.

Still of Frank Sinatra in Black Tie

Be like Frank! Take pride in your

Black Tie

While he was willing to be more loose and free with his day looks, Frank Sinatra was never slouchy when it came to formal wear. He understood that on more formal occasions, a stricter adherence to rules and conventions was necessary to respect the dress code and by extension, everyone else at the party. Later in life, Sinatra did sometimes fall victim to notched-lapel tuxedo jackets and oversized butterfly bow ties, but on the whole, he avoided the more egregious trends of that era.

Frank Sinatra with Oscar in Color

“For me, a tuxedo is a way of life. When an invitation says Black Tie Optional, it is always safer to wear Black Tie.”

Frank Sinatra

Frank Sinatra’s Personal Style Rules

Frank Sinatra and Mia Farrow at the Black and White Ball
Frank Sinatra and Mia Farrow at the Black and White Ball.
  • The hat is a hallmark. 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.
  • No brown, white, grey, or blue after the sun goes down unless it’s midnight blue. After dark, men should wear black.
  • Wear conservative silk ties
  • Cuff links always. But leave the fancy jewelry to Sammy.
  • When dressing formally, a vest is better than a cummerbund.
  • Don’t wear a tuxedo on Sunday.
  • Having messy closets is like putting on clean clothes over dirty underwear.
  • The shower is a great place to steam out the wrinkles in your dinner jacket.
  • Orange is the happiest color.
  • Don’t hide your scars. They make you who you are.
  • When it comes to pockets, everything should have its own place.
  • Wear a pocket square that is perfectly folded.
  • Shine your shoes.
  • Trim. Buff. Clean. But always make it look easy & nonchalant.
  • Take your hand off the suit.

Comparing Style Icons: Cary Grant and Frank Sinatra

Contrasting the Looks of Two Titans of 20th-Century Menswear

To better understand the personal style of Frank Sinatra, let us contrast his approach to Classic Menswear with that of one of his contemporaries and fellow Thespians, Cary Grant.

As we discussed in our video on what Classic Style really is, Grant’s personal style was always about finding the middle ground. Essentially, on a scale of 1-to-10, dialing everything to five, or halfway between boring and conservative and bold and flashy.

Sinatra, conversely, tended to set things to a 6: nothing extreme, but clearly leaning towards the exuberant, the bold, and the dashing.

Photo of Cary Grant and Frank Sinatra
Cray Grant and Frank Sinatra while filming The Pride and the Passion (1957).

An Example of Frank Sinatra’s Finely-Tuned Sense of Flash

Photo of Frank Sinatra at Heathrow in 1961
Frank Sinatra arriving at Heathrow in 1961 wearing a day suit and opera pumps.

As an example of Frank Sinatra’s propensity for dialing up his style to a 6, or maybe even a 7, let’s consider this look he sported in 1961 shortly after touching down at Heathrow Airport.

Here, Sinatra has paired a dark three-piece suit with opera pumps. Obviously, this is a unique twist on air travel attire, but rather than dress down his look, which would be the typical impetus today, Sinatra breaks style convention by scaling his footwear formality upwards.

While he is technically breaking a common style convention, because Sinatra is leaning into the formality of the look, the overall results aren’t distracting or objectionable.

Should you try to pull off flashy shoes? Find out here!

How Frank Sinatra’s Personality Made Him Stylish

Obviously, we can’t talk about Frank Sinatra’s style without acknowledging his vivacious personality. Ultimately, it’s the man that matters, not the clothes. In particular, we’d like to highlight the ways that Sinatra comported himself according to what we believe it means to be a gentleman today.

Photo of Frank Sinatra on Stage

Be Confident Without Putting Down Others

Sinatra was famous for his swagger and confidence, but without pride or obstinance … aside from the occasional scuffle or scrap, that is. And he didn’t need to insult others to elevate himself. Harnessing that confidence by dressing well is one thing that we love about Classic Style and is a great lesson to take from Ole’ Blue Eyes.

Photo of Frank Sinatra being served

Share the Wealth When You Can

Sinatra was also known for his generosity and was a renowned big tipper. While it is often assumed that those who dress well must be wealthy, we know that Classic Style adherents come from all economic backgrounds. So whether you have to scrimp and save like Raphael did when he was flat broke or can afford to splash some cash every now and then, follow Frankie’s example and remember that when luck has been a lady, nothing’s more stylish than sharing the wealth.

Photo of Frank Sinatra leaving his signature in concrete at Grauman's Chinese Theatre in Hollywood, California on July 21, 1965

Never Stop Working Hard

The son of poor Italian-American immigrants from Hoboken, New Jersey, everything that Sinatra achieved – his wealth, his fame, his style – came at the cost of leveraging his talent, hard work, and determination. So, when starting out on your personal style journey, remember the lesson to do whatever you do with all of your heart. But, be sure to stop and have fun whenever you can.

Photo of Frank Sinatra in sport shirt and cardigan

Make Your Style Your Own

Ultimately, Frank Sinatra became a style icon because he learned how to adopt and adapt Classic Style conventions to suit his own style and his own personality. Superficially, not much distinguished Frank Sinatra from the countless other men on the street, but it was in embracing what made him different and unique that allowed Sinatra to shine. Keep that in mind as you figure out how you fit into Classic Style by being true to yourself and not compromising where it matters.

Our Tips for Emulating Frank Sinatra’s Style

Closing with an emphasis on the ways that Frank Sinatra’s take on Classic Style can influence your own, let’s run down a quick list of seven style tips that you can easily integrate into your own looks. And what better way to do it than with references to classic Frankie tunes?

1
Preston's minimalist wallet

That's Life

No matter your circumstances, you can make Classic Style work for you, even if it requires pinching a few pennies now and then. Just roll with the punches and keep on swinging!

2
Raphael teaching his daughter how to button her cardigan

It Was a Very Good Year

From his start as the beau of the bobby soxers to his end as the dignified Chairman of the Board, Sinatra knew that to everything there is a season.
So enjoy all that every stage of life has to offer by dressing your age.

3
Photo of a man in a white suit

Summer Me, Winter Me

To really savor what each season brings, acknowledge Frankie’s Italian roots by embracing seasonality and scorpacciata, altering your wardrobe to match the spirit of the season.

4
Raphael displays two dotted bow ties, one with small white dots on a yellow ground and the other with larger blue dots on a golden ground

It Had To Be You

While on your lifelong style journey, build a personalized, high-quality wardrobe with lots of accessories you love to make every individual item go further.

5
Preston, smiling, gives a thumbs up gesture

Let Me Try Again

When you commit a fashion faux-pas or find yourself with a junked-up wardrobe, just pick yourself up and start over again. Trust us, we’ve all made mistakes while learning the style ropes.

6
Belstaff Sleeve Measuring

The Best Is Yet To Come

Keep your chin up even when confronting little mistakes, because your style journey is constantly developing. Enjoy the trip! And know that the Gentleman’s Gazette is here to help on every step of the way.

7
Three different gentlemen with the same love for classic style: Preston, Kyle, and Raphael.

My Way

Classic Style wouldn’t be anything without the unique contributions of stylish gentlemen like Frank Sinatra. And as a constantly evolving mode of dress, there’s plenty of room for your style inside Classic Style. So never forget that while you’re learning about Classic Style, you also need to be true to yourself.

Conclusion

As one of the most stylish, talented, and famous men of the 20th century, Frank Sinatra blazed a remarkable career and lived an extraordinary life that was only partially defined by his remarkable grasp of Classic Style. We hope that what you have learned today will inspire you to get swinging and live life with a stylish song in your heart. Just make sure that you do it … your way!

Let us know in the comments, what do you think made Frank Sinatra so stylish?

Hear Preston’s interpretation of “The Way You Look Tonight!”

Today’s Outfit Rundown

Photo of Preston dressed with Frank Sinatra inspiration
See how Preston drew inspiration from Frank Sinatra’s style in today’s Outfit Rundown.

Channeling Frank Sinatra’s outfit when he arrived at Heathrow Row in 1961, Preston is wearing a charcoal-gray three-piece suit with a unique weave. His white shirt has French cuffs, worn with a pair of vintage cufflinks that set off his Fort Belvedere collar clip.

Preston’s tie is a vintage piece from Robert Talbott with a Macclesfield neats pattern in orange. Making Frank Sinatra’s favorite color a centerpiece of this look, that shade also appears on Preston’s white-edged pocket square and his Fort Belvedere Orange Exotic Caribbean boutonniere.

On his head, Preston is wearing a vintage charcoal gray fedora with a short brim, and on his feet are his opera pumps. To dress down these very formal shoes, he has paired them with shadow stripe charcoal and orange cotton socks from Fort Belvedere.

Collar Clip by Fort Belvedere, gold yellow rose silver platinum

Fort Belvedere

Collar Bar Clip in Yellow Gold

Silk Pocket Square in Orange, Blue, Green,Red and White with Large Paisley Pattern - Fort Belvedere

Fort Belvedere

Silk Paisley Pocket Square with White Border

The same pair of half-boots black Oxfords, this time with black shoelaces (Pictured: Shadow Stripe Ribbed Socks Charcoal and Orange from Fort Belvedere)

Fort Belvedere

Charcoal and Orange Shadow-Striped Socks

Orange Exotic Caribbean Boutonniere Buttonhole Flower Fort Belvedere

Fort Belvedere

Orange Exotic Caribbean Boutonniere

Reader Comments

  1. 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. 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. 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. 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. 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.

    1. Quite so on the Harry James and Tommy Dorsey . I in fact did know Harry James first wife , herself a band singer and she often spoke of seeing Frank with Tommy Dorsey . Frank sang first for Harry .

      Let us please see a bit on Fred Astaire . He was a style icon ; never anyone better .

  6. 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: http://www.ivy-style.com/golden-years-my-brief-bromance-with-frank-sinatra.html 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
    http://www.seitelman.com

    Sinatra loved the

  7. 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. 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.

  9. One quick style-related note… I absolutely LOVED his bit in the movie “The Tender Trap” where he rushes in to his Manhattan playboy apartment in a hurry to get ready for a date… changes to a fresh shirt and lathers & shaves, in one fluid set piece while talking to his buddy. Seamless grace folded into playful badinage and a “how to shave” lesson to boot!

  10. While Sinatra’s personal life may not have been an ideal example of being a gentleman, there is no denying the man had style. Of all of the stylish actors of that era he was head and shoulders above most. Only Fred Astaire and Cary Grant really gave him a run for the money. I have been a fan of all three for decades and have occasionally copied, as best I could, some outfits from each of them. I found that being able to create stylish looks like theirs doesn’t come naturally to me, but with the ensemble already tried and true, it works well for me. And, not really surprisingly, I almost always get complimented on what I am wearing when I borrow their look.

  11. Artists know that orange, Sinatra’s favorite color, is the color opposite of blue on the color wheel, meaning that it sets it off well and calls attention to it: Old Blue Eyes!

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