The World's Most Stylish Men at 40
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.
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.
Denzel Washington. 1995.
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.
Michael Jordan. 2003.
Jordan was still menacing defences 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 moustaches 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.
The Crown has 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).
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