The Most Stylish Dads of All Time

Fatherhood doesn't mean the end of fashion sense.

The Most Stylish Dads of All Time
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The term “dad style” conjures images of washed-out denim, white sneakers, and oversized pique polos. (See: Jerry Seinfeld.) In other words, “dad style” tends to not really be style at all. To the stereotypical father, getting dressed—like brushing your teeth or putting on deodorant—is just one more item on the morning to-do list.

To the stylish dad, on the other hand, getting dressed is a labor of love. In between raising kids and holding down extremely high-profile gigs, the following men are living, breathing proof that good style doesn’t go out the window with fatherhood. Think of it less as a ranking of style icons and more as a pantheon of style gods.

1
Paul Newman

paul newman on the set of towering inferno, most stylish dads Alamy

Late screen legend Paul Newman is hands-down the most stylish actor/race-car driver in history. (Sorry, Patrick Dempsey.) He looked just as great wearing slim-lapeled gray tailoring at political affairs (as seen in the 1963 March on Washington) as he did wearing off-duty digs on the big screen (as seen in the 1974 thriller, Towering Inferno, above). That he was also a father of six while looking so consistently fashionable—for so long—is nothing short of Olympian. Oh, and he also founded a food company, Newman’s Own, that sells everything from cookies to salad dressing to lemonade—and donates 100 percent of its profits to charity.

2
Dwayne “The Rock” Johnson

dwayne the rock johnson with simone johnson Shutterstock

Named People’s Sexiest Man Alive in 2016, Dwayne “the Rock” Johnson has had an impressive style shift over the years. As a member of the World Wrestling Federation, for years, most of his public appearances involved a whole lot of spandex—and little else. Nowadays, he’s evolved to form-flattering polos, patterned slacks, chunky merino knits, and (as seen above, next to eldest daughter Simone Johnson) impeccably cut summer-grade tailoring. Johnson is so stylish now that, in May 2017, he even scored a GQ cover shoot.

But the father of three is more than just a fashion icon. He’s also a bona fide trendsetter: In a 2019 Instagram post, he singlehandedly made the case that workout tights can work on dudes. (To be fair, though, with quads like Johnson’s—which are practically topographical maps of the Andes—any type of pants would work.)

3
Barack Obama

barack obama former president at an international food meeting in milan, most stylish dads Shutterstock

Whatever you think of the man, there’s no arguing that 44 is a seriously stylish guy. Now a full-blown private citizen, Barack Obama has stuck with the wardrobe of flawlessly tailored Brooks Brothers suits, but has tossed out the neckties for open collars. Outside of public events, he’s been frequently spotted wearing the type of rugged brown leather jackets he used to rock in his law school days.

Even the fashion pros at Harper’s Bazaar have taken note, remarking that, “both he and Michelle are coming into their personal styles post-Pennsylvania Avenue, rocking looks we likely would not have seen them sport during their time in Washington.” Former first daughters, Sasha and Malia, should be proud.

4
Ryan Gosling

ryan gosling on the red carpet for cannes, most stylish dads Shutterstock

If there’s a man alive today who could inherit Steve McQueen’s old mantle, “the King of Cool,” it’s Ryan Gosling. Put him in a leather bomber and tattered tee (Drive); he looks great. Put him in a 1920s-era newsboy get-up (The Notebook); he looks great. Put him in a futuristic fur-lined topcoat and combat boots (Blade Runner: 2049); he looks great! Point is, if it counts as clothing, Gosling looks good wearing it.

And then there’s his signature off-screen sleeve style. Gosling frequently deploys a military cuff—a variation on traditional rolls for a tighter look that shows off just the right amount of bicep (as seen in the photo above).

It also can’t hurt when he’s playing with his two daughters, whom he had with longtime partner Eva Mendes. “When you meet your kids, you realize that they deserve great parents,” Gosling told GQ in 2016. “And then you have your marching orders, and you have to try and become the person that they deserve.”

5
Carey Grant

carey grant portrait, most stylish dads Alamy

Yes, with his meticulous hair and elegant suits, the late Cary Grant was the very definition of “dapper.” But good style isn’t just about what you wear—it’s about how you think and act and feel, too. What makes Grant—who had one daughter at 62—one of the most stylish dads in history is the fact that, for decades, he was nothing if not consistent. As Grant himself wrote in The Week, “In all cases, the most reliable style is in the middle of the road… And so it should be with clothes.”

Once his daughter Jennifer was born in 1966, Grant’s focus changed entirely. “She’s my best production,” he used to say, according to The Montreal Gazette.

6
Idris Elba

idris elba Shutterstock

People’s Sexiest Man Alive in 2018, Idris Elba OBE (yup, he’s a knight, too) is no stranger to style. On the red carpet and off, he rocks flashy patterns and trendy cuts with unrivaled confidence. The father of two is so truly above and beyond in the wardrobe department that, over on the popular men’s fashion blog Style Girlfriend, he won the reader poll for Most Stylish Man of 2019—beating a whole bunch of other stylish dads, including Bradley Cooper, Jason Momoa, and Paul Rudd.

7
Humphrey Bogart

humphrey bogart candid, most stylish dads Alamy

In the 1940s, when Humphrey Bogart was at the height of his power, fedoras weren’t just cool, they were practically mandatory—and nobody wore one like Bogie did, always a few degrees off-axis. His go-to choice of clothing—wide-lapeled, billowy suits, which you’d never see in the 21st century—was just a natural extension of his inherent nonchalance. And then there was the manner in which he’d let a cigarette effortlessly dangle out of his mouth (which we didn’t know at the time was more deadly than debonaire).

Many of the movies that made the notoriously absent father of two a style icon haven’t exactly aged well. But the man himself, like a fine wine, has only grown more distinct as the years go by—even though he died more than 60 years ago.

8
Jeff Goldblum

jeff goldblum on the hollywood walk of fame, stylish dads Shutterstock

In the Jurassic Park era, Jeff Goldblum was like any other male A-lister: good-looking, sure, but dressed no different than any other guy walking down Sunset Boulevard. Then, somewhere in the mid-2010s—somewhere on the road between The Grand Budapest Hotel and Thor: Ragnarok—he picked up Andrew T. Vottero as a stylist. From there on out, it was all Raf Simons fashion shows and GQ shoots.

He also had two sons along the way, with his wife, Emilie Livingston, the former Olympic gymnast. Thankfully, fatherhood hasn’t stopped Goldblum, 66, from turning heads: In early 2019, he showed up at the Sundance Film Festival with three high-minded winter looks so distinct they belong in a museum.

9
David Beckham

david beckham at cannes

Generally, stylish men fall into one of two camps: scruffy, tatted-up, devil-may-care rocker types; or groomed, suited-up, not-a-hair-out-of-place gala types. David Beckham might be the only man on the planet who falls effortlessly into both—and he has no hesitations about passing the baton. Just look at his eldest of four, Brooklyn Beckham, a model, who has quickly become a bona fide style icon in his own right. No doubt the Beckhams have style baked into their genes.

10
Brad Pitt

brad pitt at cannes in 2012 Shutterstock

Brad Pitt has a superpower: Anything that should look sleazy on anyone else looks fantastic on him. Just look at this photo of him at the Cannes Film Festival, in 2012. The star wore a muted olive suit (no), a V-neck deeper than the Mariana Trench (no!), two gold chains (No!), greasy Kurt Cobain-esque locks (NO!), and some villainous goatee-and-sideburns facial hair (NOO!!). On paper, on anyone else, this would be remembered as the worst look in menswear history—and yet, Pitt looks like the hottest model in a John Varvatos catalog.

For the good of fashion, let’s hope his six children pick up the power, too.

11
John Legend

john legend and wife chrissy teigen, stylish dads Shutterstock

John Legend is one of just 15 people to nab the coveted EGOT (meaning: he’s won Emmy, Grammy, Oscar, and Tony awards); needless to say, he goes to a lot of awards shows. So it’s no wonder that he always looks on-point in a suit, whether he’s wearing his signature all-black head-to-toe or something with a bit more flair, like this ’70s-inspired getup. The fact that he’s managed to fit in being a father to two—with his wife, supermodel and mega-watt Twitter star, Chrissy Teigen—in the process is nothing short of commendable.

12
Sean Connery

Sean Connery in the 60s, most stylish dads Alamy

By all accounts, Sean Connery is James Bond. (Sorry, Roger Moore fans.) By suiting up as fiction’s suavest protagonist for seven films over three decades, Connery, a father of one, automatically ranks among history’s most stylish dads. But his dashing looks weren’t reserved for just one role. In all of his films—from Alfred Hitchcock’s Marnie to the original Murder on the Orient Express—Connery, who’s pushing 90, carries himself with an insouciance that can’t be taught or bought.

13
George Clooney

george clooney wearing a tux at the venice film festival in 2017 Shutterstock

You don’t need us to tell you that George Clooneytequila tycoon, notorious prankster, and father of twins—is a well-dressed guy. But the key to Clooney’s style isn’t that he wears great clothing (though that of course helps). It’s that he wears it in an era-defying way, reminiscent of Old Hollywood style icon Clark Gable. And the comparisons don’t stop at the wardrobe. In 2013, Esquire drew a direct line between the two: Clooney lived in Gable’s house in L.A.!

And having twins in 2017, with his wife Amal Clooney, certainly hasn’t slowed his style game now, though it has changed his perspective. “I am at last experiencing what most people in the world get to experience, which is the incredible amount of love you gain when you have two children you are responsible for,” Clooney told Daily Mail.

14
Ryan Reynolds

ryan reynolds blake lively and their two kids Shutterstock

On-screen, he’s most famous for wearing either skin-tight red spandex, or nothing at all. But in real life, the man behind Deadpool is quite a dapper dad—to two daughters, with his wife, Blake Lively. Knit ties, blue wool overcoats, suede bombers, and gray flannel suits are all part of the Ryan Reynolds repertoire; and he can pull it all off with ease.

15
Kanye West

kanye west and kim kardashian on the red carpet Shutterstock

Love him or hate him, Kanye West’s stature in the world of fashion is undeniable. Perhaps more than any other individual in the industry, West has helped usher in a new era of streetwear. His fashion lines (billed as “seasons,” like a TV show) tend to set the internet on fire and regularly make headlines in outlets like the New York Times or Hollywood Reporter. His signature shoes, the Adidas Yeezy Boost, go for hundreds of dollars on eBay—and that’s at resale! No two ways about it: This father of four has some major style power, just like his wife, Kim Kardashian West.

16
Gregory Peck

gregory peck portrait, most stylish dads Alamy

Standing 6’3″ and with a jaw so sharp it could cut glass, Gregory Peck is the epitome of tall, dark, and handsome. He’s also the epitome of “righteous dad”—not only because he had five children of his own, but because of his portrayal of Atticus Finch, in the 1962 movie To Kill a Mockingbird. In fact, his turn as Finch was so unforgettable that Oliver Peoples, the high-end eyewear designer, has a best-selling model inspired by his frames in the film, which are fittingly called the “Gregory Peck.”

He died in 2003, but it’s safe to say Peck enjoyed his roles as a style icon, father, and actor along the way. “I just do things I really enjoy,” he once said, according to the Los Angeles Times. “I enjoy acting. When I’m driving to the studio, I sing in the car. I love my work and my wife and my kids and my friends. And I think, ‘You’re a lucky man, Gregory Peck, a damn lucky man.'”

17
Oscar Isaac

Oscar Isaac Alamy

As any style-minded guy knows, grooming counts just as much as clothing. And few men are more perfectly groomed than Star Wars actor and father of one Oscar Isaac. First, there’s the hair. Whether bushy and unkempt (as seen in Inside Lleywn Davis), shorn to a millimeter (Ex Machina), or free-flowing like a river (Annihilation), it works. And then there’s the stubble. By presumably some form of magic, Isaac has permanent two-day stubble—the exceptionally rare type of facial hair that eludes everyone but the most well-groomed European men.

18
Tom Ford

tom ford on the red carpet, most stylish dads Shutterstock

Tom Ford singlehandedly resurrected Gucci. He brought Yves Saint Laurent back from the brink of obsolescence. He launched his own luxurious, extremely aspirational brand. He literally designed suits for James Bond (specifically, the Daniel Craig installments). No matter where Ford goes, the world’s suavest people wear his clothing—so it should be no shock to hear that Ford, a father of one, is one of the world’s suavest people.

Though he famously told Mr. Porter, “I feel less sexy now that I’m a father,” we couldn’t disagree more. Need proof? Just look at that powerful, deep blue velvet tux.

19
Steve McQueen

steve mcqueen candid photo, most stylish dads Alamy

Direct your eyes up at the King of Cool and father of two. Need we say more? And for more style inspiration through the years, here’s The Most Popular Menswear Style the Year You Were Born.

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