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.
“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
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.
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
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
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
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
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.
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.
“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
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.
“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.
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
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.
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.
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.
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
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
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
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.
Contrasting
Dark and Light Colors
Contrasting
Patterns & Textures
Contrasting
The Bold & Sedate
“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
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
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.
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
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.
“Cock your hat – angles are attitudes”
Frank Sinatra
Garments Perfectly Employed By Frank Sinatra
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.
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.
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”
“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.
Learn the secrets to properly wearing men’s jewelry!
Frank Sinatra Properly Cared For His Clothing
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.
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.
“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
- 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.
An Example of Frank Sinatra’s Finely-Tuned Sense of Flash
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.
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.
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.
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.
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?
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!
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.
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.
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.
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.
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.
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
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.
