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How to Be Dressed Like Dean Martin

Born Dino Paul Crocetti (June 7, 1917 – December 25, 1995), Dean Martin was an American actor, singer and comedian, best known for his laid-back demeanour, charisma, and sophisticated style, whether he was wearing a suit and necktie or a tuxedo and bow tie.

Martin exuded self-assurance in everything he did, from his signature relaxed, warbling, crooning voice in his hit songs to his film roles and appearances on radio and television. This ultimately earned him the moniker "The King of Cool."

Let's look at how you can emulate his cool guy dress style.

Dean in his early days

The Rise of Dean Martin

Born in Steubenville, Ohio, Dean's early years were immensely varied and colourful, to say the least. He worked as a bootlegger, a steel worker, a casino worker, a blackjack dealer, a boxer, and an amateur musician. Through his amateur singing gigs and varied businesses with club owners, he got his first professional singing gigs with local bands.

(Dean Martin and Jerry Lewis during a promotional shoot for their NBC broadcast, 1955.)

In the mid-40s, Dean partnered with Jerry Lewis to form a radio program called The Martin and Lewis Show. The zany Lewis constantly bounced off the unflappably smooth Martin in a partnership that spanned 10 years across nightclubs, radio and television shows, and film. In the summer of 1956, the duo split to pursue different career paths.

(Dean with his friend Frank Sinatra during one of the countless dinner parties they attended in their heyday, around 1961. The men wear bow ties and tuxedos.)

After Dean Martin's early success in the war drama The Young Lions (1958), he landed multiple acting roles in the following years, including the Vincente Minnelli drama Some Came Running (1958), where he first acted alongside Frank Sinatra. He would also lend his singing talents and relaxed cool vibe to his familiar venue of nightclub shows in Vegas, plus radio and TV shows.

(One of Dean Martin's many record albums, this one recorded with Capitol Records in 1957.)

(The Rat Pack, August 1960. From left to right, Frank Sinatra, Dean Martin, Sammy Davis Junior (centre), Peter Lawford and Joey Bishop.)

During this period, Dean was part of the infamous Rat Pack through his friendship with Sinatra and the other members: Sammy Davis Jr., Peter Lawford, Joey Bishop, and others. They were an informal group that would do shows together in Vegas and would also star together in a few films like Ocean's Eleven (1960), Sergeants 3 (1962) and Robin and the 7 Hoods (1964). Dean's association with the group helped him build his signature persona as a smooth, easy-going, free-wheeling boozing playboy even though, in reality, he often drank apple juice in place of whiskey at his shows and was a dedicated family man.

Dean Martin during a recording session of "Sleep Warm"

(Dean Martin during a "Sleep Warm" recording session with Capitol Records, Frank Sinatra conducting and with arrangements by Pete King. Approximately October 1958.)

Around this period, Dean's single "Everybody Loves Somebody" managed to beat the Beatles at their height on the top spot of the 1964 billboard charts, even though the 1950s were giving way to the early rock 'n' roll scene of the 1960s. His single would stay high on the "Pop-Standard Singles" chart for eight weeks. His other well-known songs are "Ain't That a Kick in the Head," "You're Nobody 'Til Somebody Loves You," "The Door Is Still Open to My Heart," and "Send Me the Pillow You Dream On."

(Dean Martin in the recording studio in the 1960s.)

Dean Martin's most famous act was his show on the NBC network called The Dean Martin Show. Running from September 19, 1965, until April 5, 1974, the hour-long variety show featured him singing solos or duets with his guest stars. It included his comedic antics from his nightclub performances. His shows were usually unrehearsed, so most of his reactions were genuine. Dean attributed his success to his unpretentiousness — in fact, any mistakes he made would go directly into the tape.

Throughout his various stints and acts as a multi-talented entertainer, Dean ensured that he would forever be the cool, casually understated straight guy among his famous peers in the Rat Pack — whether to contrast with Sinatra's intense perfectionism or Davis's extravagant fervour. His dress reflects his attitude, trying to be as elegant and stylish with as little effort as possible. Here, we examine his dress style throughout the years.

How to Dress Like Dean Martin

(His role as the drunken, work-shy playboy host for the show had him don a tuxedo throughout the show's nine seasons, so he had plenty of time to hone his look.)

(The exact styling of his tuxedo changed over the years to keep with the era's latest trends, but a few similarities still exist. For example, in solidarity with his fellow Rat Pack members, Dean always tried to include orange or red in his outfit. In this case, it's an orange pocket square with his tuxedo.)

(Sticking with timeless designs and occasionally making a few concessions to the era's trends.)

(Dean Martin takes a break during a recording session in Los Angeles, California, in approximately 1958, possibly recording a Christmas special.)

While Dean isn't as dedicated as, say, his friend Sinatra in following a particular style, there are a few specific tailoring tips he used whenever he had a suit or outfit made, whether it was by the Rat Pack's unofficial tailor Sy Devore or elsewhere: Collars had to be made a little taller to minimise his long, thick neck, and the sleeves made a little longer to hide Dean's big hands, which he bruised and battered during his early boxing years.

Dean Martin proved that some style elements, such as smoking jackets, turtlenecks, and a well-fitting tuxedo, are still trending after all these years. And, of course, ties are always in fashion, regardless of era. Thanks, Dean, for all the memories and style tips.