How His Style Was Influenced by Dean Martin in Red – WWD

On Friday, legendary musician Tony Bennett died at age 96. Bennett had one of the most critically acclaimed careers in music and entertainment, scoring numerous awards, including 20 Grammy Awards and two Primetime Emmy Awards.

The famed musician performed with numerous fellow A-list stars throughout his career, from Christina Aguilera to Aretha Franklin. Bennett was also a Kennedy Center honoree. In total, he sold more than 50 million records worldwide.

Throughout his time in the public eye, Bennett was known for his love of suits. Bennett once said 95 percent of his suits, ties and pocket squares were from Italian luxury brand Brioni. A red pocket square became his signature look for getting attention — a styling hack used by Dean Martin and Sammy Davis Jr., who stood out among their Rat Pack cohorts Frank Sinatra, Joey Bishop and Peter Lawford.

“Dean told me to always have a red handkerchief in my [breast] pocket,” Bennett said in an interview with the Los Angeles Times. “Now everybody does that, but at that time, it was brand-new. He did it for television.”

red pocket square, red handkerchief, THE DEAN MARTIN SHOW -- Episode 328-- Pictured: (l-r) Host Dean Martin, singer Tony Bennett-- (Photo by: NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images)

Dean Martin, left, and Tony Bennett on “The Dean Martin Show” on March 21, 1968.

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WWD looks back at his style and celebrity friends through the years.

Diana Ross, 1973

In 1973, Bennett joined fellow singer Diana Ross for the premiere of “Lady Sings the Blues” in London. Ross starred in the film as famed jazz singer Billie Holliday. Bennett wore one of his classic suits with a micro-dot tie and pocket square for the premiere.

Diana Ross, Tony Bennett suits, Lady Sings the Blues, celebrities

Singers Diana Ross and Tony Bennett attending the premiere of the film “Lady Sings the Blues” in London on April 5, 1973.

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Luciano Pavarotti, 1981

Tony Bennett, Luciano Pavarotti, Washington DC

Tony Bennett, left, and Luciano Pavarotti attend a fundraising event, including a performance recorded for television, at Ford’s Theatre in Washington, D.C., on March 21, 1981.


In the 1980s Bennett’s music career was in full swing and Pavarotti was one of the brightest opera stars in the world. At a fundraising event in 1981, Bennett donned a suit and top coat while Pavarotti was clad in a fur hat and coat at a fundraising event in Washington, D.C.

Dolly Parton, 1993

Dolly Parton, Tony Bennett, Lincoln Center

Dolly Parton and Tony Bennett attend an event at Lincoln Center in New York City on May 13, 1993.


Bennett performed at Lincoln Center many times and attended events held at the music and performance venue. In 1993 he joined country singer Dolly Parton for an event wearing a pin-striped suit and patterned tie.

Christina Aguilera, 2007

Tony Bennett, Christina Aguilera, Emmy Awards

Singers Tony Bennett and Christina Aguilera perform onstage during the 59th Annual Primetime Emmy Awards on Sept. 16, 2007, in Los Angeles.

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At the 59th annual Emmy awards, Christina Aguilera got pretty in pink while Bennett donned a black suit and pearl white tie to perform a duet. His red pocket square was becoming his signature accessory.

Aretha Franklin, 2011

Aretha Franklin, Tony Bennett, Met Opera

Aretha Franklin and Tony Bennett perform onstage during Tony Bennett’s 85th birthday gala benefit for Exploring the Arts at the Metropolitan Opera House on Sept. 18, 2011, in New York City.

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The queen of soul Aretha Franklin joined Tony Bennett onstage for a performance at his 85th birthday benefit gala. Bennett was in a suit and again had his signature red pocket square.

Carrie Underwood, 2012

Carrie Underwood, Tony Bennett, Grammy Awards

Singers Tony Bennett and Carrie Underwood perform onstage at the 54th Annual Grammy Awards held on Feb. 12, 2012, in Los Angeles.

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At the 54th annual Grammy Awards, Bennett donned his signature black suit and red pocket square, but this time with a black patterned tie. He was joined by country music star Carrie Underwood, who wore a black and gold beaded dress for their performance.

Lady Gaga, 2015

Lady Gaga, Tony Bennett, Grammys, Best Pop Vocal Album

Singers Lady Gaga and Tony Bennett, winners of Best Traditional Pop Vocal Album for “Cheek to Cheek,” pose in the press room during the 57th Annual Grammy Awards on Feb. 8, 2015, in Los Angeles.

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Tony Bennett was arguably one of Lady Gaga’s biggest celebrity fans. The two won a Grammy Award for Best Traditional Pop Vocal Album for “Cheek to Cheek” in 2015. Gaga credits Bennett with being the reason she continued music when she thought about quitting.

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