How the World's Most Stylish Men Looked at 40
How the World's Most Stylish Men Looked at 40
A confession: When I turned 40 last year, I felt insecure about how I looked: my clothes, my hair, my skin. I wasn't concerned about looking old—okay, maybe a little—but instead looking complacent. Like I stopped caring (even though, paradoxically, I try very hard to look like I don't care, even though I care very much). I didn't buy a closet full of new clothes, change my hair, or alter my skincare routine. I sought inspiration. I created a moodboard of famous people when they turned the big four-o. I wanted to see how they dressed and looked. I started sharing the moodboard with friends staring down 40, and then decided, what the hell, why not share it with Esquire readers.
Here it is: an incomplete collection of notable men at the precise age of forty. I hope you enjoy it, whatever age you might be.
David Bowie. 1987.
Bowie is all the style inspiration a person turning 40 needs: effortlessly cool. The year he turned 40, Bowie released the record Never Let Me Down.
James Baldwin. 1964.
Baldwin is one of the greatest American writers of all time (and a frequent Esquire contributor) who, a year before turning 40, was on the cover of Time magazine.
Leonardo DiCaprio. 2015.
When DiCaprio turned 40, he was promoting The Revenant, which earned him an Academy Award for best actor.
How the World's Most Stylish Men Looked at 40
At 40, Washington was one of the most exciting (maybe the most exciting) actors alive. That year he was in Crimson Tide and the adaptation of Shakespeare's Much Ado About Nothing. He also had four kids under the age of eleven!
Sean Connery. 1970.
A year before Connery celebrated his 40th birthday, he returned to the James Bond franchise in Diamonds Are Forever. Also, he's the oldest looking forty-year-old in the bunch.
Steve McQueen. 1970.
At 40, McQueen was in the prime of his career. Two years earlier, he starred in Bullitt and The Thomas Crown Affair. The following year he'd be in Le Mans and then, a year later, The Getaway.
Bruce Springsteen. 1990.
Forty-year-old Springsteen rocked scruff, a tousled mop, and a mostly-unbuttoned patterned shirt. He was between records at the time, but continued to perform live.
Michael Jordan. 2003.
Jordan was still menacing defenses at 40 while playing his final season in the NBA for the Washington Wizards, where he averaged 20 points a game and made the All-Star team. (In this picture he's sitting court side with Patrick Ewing during a Knicks-Magic game, when Ewing's jersey was retired.)
Robert Redford. 1976.
Fresh from All the President's Men, Redford at 40 had one of the best mustaches in Hollywood history. Also, a phenomenal sweater, shirt, and sport coat combination.
Alain Delon. 1976.
Always a tough guy—even at 40, especially at 40—looking tough in a white suit.
Prince Charles. 1989.
If The Crown is to be believed, Prince Charles was quite a shit to Princess Diana. But the show also made us aware of his incredible style. Here he is attending a camel race in Abu Dhabi.
Prince. 1998.
Prince performing in Paris. No one ever looked better at 40—or any age—than Prince.
Burt Reynolds. 1977.
Reynolds was in the prime of his career at 40, the year he made Smokey and the Bandit.
Muhammad Ali. 1982.
One year after his final fight, 40-year-old Ali sat front row at a Valentino fashion show next to Bianca Jagger and Calvin Klein.
Ernest Hemingway. 1939.
At 40, Hemingway, pictured here in Wyoming, decamped to Havana, left his second wife, Pauline Pfeiffer, for the woman who would become his third wife, Martha Gellhorn, and began work on For Whom the Bell Tolls. (Hemingway didn't like this photo, saying, "I don't work like this.")
Brad Pitt. 2004.
Pitt starred in two blockbusters, Troy and Ocean's 12, the year he turned 40. He also started filming Mr. and Mrs. Smith, the movie on which he met Angelina Jolie.
Marvin Gaye. 1979.
Forty was a difficult year for Gaye, who recorded a disco record, Love Man, to help pay off back taxes he owed the IRS. He would eventually shelf the record. Three years later, he released his biggest hit, Sexual Healing.
John F. Kennedy. 1957.
The year before he turned 40, then-Senator Kennedy was critically ill and underwent several spinal surgeries. At one point he was administered Catholic last rites. The next year, at 40, he won the Pulitzer Prize for Biography for his book Profiles in Courage. Three and a half years later he was elected president.
Miles Davis. 1966.
Five months before turning 40, Davis was hospitalized for a liver infection. His record sales were also declining. Soon, however, he would form a new band and record, Miles Smiles, which came out in 1967 to critical acclaim, pointing a new way forward for Davis.
Bruce Willis. 1995.
Willis was coming off the success of Pulp Fiction when he turned 40. He was also establishing himself as a restaurant man thanks to his involvement with Planet Hollywood.
Jack Nicholson. 1977.
Nicholson, who was dating the much-younger Anjelica Huston, had reached peak Nicholson at 40 (the shades, the suit, the smoke).
Jay-Z. 2009.
Just before turning 40, Jay-Z signed a massive deal with Live Nation, started his own record label, put out his 11th album, The Blueprint 3, and went on a world tour. At 40, he went into the studio with Kanye West to record Watch the Throne.
Mick Jagger. 1983.
Jagger's 40th birthday was a big deal for Boomers. To mark the occasion, The Who's Pete Townshend wrote an essay for Rolling Stone magazine. That year, the Rolling Stones released their 19th studio album, Undercover.
Keith Richards. 1983.
Richards marked his 40th birthday by marrying Patti Hansen.
Cary Grant. 1944.
The year he turned 40, Grant would appear in three movies, including one of his best, Arsenic and Old Lace. (In this picture, he's rehearsing lines for a radio program.)
Paul McCartney. 1982.
The ultimate family man (pictured here with his first wife, Linda McCartney) was still cool heading into 40, having been arrested for marijuana possession two years earlier. In 1982, he collaborated with Stevie Wonder on the hit Ebony and Ivory.
John Lennon. 1980.
Lennon was murdered just two months after turning 40.
Daniel Dae Kim. 2008.
Kim, who was starring in Lost in 2008, absolutely smoldered at 40.
Humphrey Bogart. 1939.
Bogart was in seven movies the year he turned 40, but his biggest hits (like Casablanca) were still a few years away. At the time, he was married to his third wife, Mayo Methot, who divorced him in 1945. Bogart then married Lauren Bacall. In 1949, he became a father for the first time.
Gael García Bernal. 2018.
Two years before turning 40, Time magazine called García Bernal one of the world's most influential people.
Martin Sheen. 1980.
Before Sheen turned 40, he suffered a heart attack and a nervous breakdown on the set of Apocalypse Now.
Bob Dylan. 1981.
Dylan was in the midst of his Christian period when he turned 40 but remained (despite it or because of it) an "iconoclast," according to the New York Times. He also started wearing suits.
Omar Sharif. 1972.
The renowned Egyptian actor was in the midst of a second career at the age of 40—as a world-famous bridge player. Also, he was the most stylish bridge player.
Leonard Cohen. 1974.
Cohen, a model of a man in a suit, was traveling the world the year he turned 40, with tours in the U.S., Canada, and Europe.
Sidney Poitier. 1967.
Already an Academy Award winner, Poitier was at the commercial peak of his career at 40—one of the nation's biggest box office draws at the time—with three films in theaters: To Sir, With Love, In the Heat of the Night, and Guess Who's Coming to Dinner.
Alex Rodriguez. 2015.
A-Rod started the baseball season of his 40th year with a suspension. That year he also became the fourth leading home run hitter of all time and set the American League record for most RBIs.
Andy Warhol. 1968.
Although Warhol was at the height of his powers in 1968, he would turn 40 while recovering from a nearly fatal gunshot wound.
Frank Sinatra. 1955.
Sinatra was just getting started at the age of 40: He was at the beginning of his major comeback, having released In the Wee Small Hours of the Morning. At the time, he was married to Ava Gardner.
Dean Martin. 1957.
The year he turned 40 was a mixed bag professionally for Martin, who had a hit single with "Volare" but a box-office flop with the movie Ten Thousand Bedrooms.
Sammy Davis, Jr. 1965.
Davis was on a hot streak at 40. He was performing with the Rat Pack, starring in films and the Broadway hit Golden Boy, and breaking color barriers. A year before turning 40, Davis became the first Black person to perform solo at the Copacabana in New York.
Forty can be a tough age, even today, especially today. But these guys—from Ernest Hemingway to Jay-Z—made it look effortless, cool, and aspirational.