Brad Pitt's Sexiest Looks Through the Years

Pitt looked James Dean-cool in his black leather jacket at the Jimmy Stewart Relay Marathon Kick-Off Cocktail Reception in Beverly Hills.

The heartthrob even made nerd chic look good!

Everything good about '90s heartthrobs is in this very picture. 

The bearded babe smized years before Tyra Banks even taught us that word when he stepped out for the New York City premiere of Johnny Suede.

Pitt was a casual cutie at the Los Angeles premiere of Zebrahead.

You are not wrong -- there is virtually no one else, even in 1993, who could have pulled off these long locks and that brown vest, which is what the Legends of the Fall actor donned for the 8th Annual West Independent Spirit Awards.

Sure, the actor looked like he should have been surfing in Venice at the Los Angeles premiere of The Legends of the Fall, but it worked for him!

Pitt looked quite handsome as he took home the award for Best Supporting Actor in a Motion Picture Drama for his role in 12 Monkeys during the 53rd Golden Globe Awards.

Pitt and then-girlfriend Gwyneth Paltrow sported matching haircuts, black jackets and sexy stares at The Devil's Own premiere in New York City.

The actor was pure hunk status at the Seven Years in Tibet premiere.

The 12 Monkeys star looked like a total rockstar in his orange sunglasses and white tee during the Tibetan Freedom Concert in Washington, D.C.

Pitt looked devilishly handsome at the New York City premiere of Meet Joe Black.

The hunky actor looked sharp at the London premiere of Snatch. In the Guy Ritchie film, Pitt played Irish boxer Mickey O'Neill.

Pitt smiled wide as he supported then-wife Jennifer Aniston at the 54th Annual Primetime Emmy Awards, where she took home an Emmy for Best Actress in a Comedy Series for Friends.

The tan Troy star looked like he had reverse-aged when he appeared on MTV's TRL.

Even blonde looked good on him! Pitt showed off his lighter locks when he hit the red carpet for the Mr. & Mrs. Smith premiere in L.A.

It was hard to take our eyes off the Babel babe during his film's gala presentation at the Toronto International Film Festival.

The dad of six was one dapper dude during a press conference for The Curious Case of Benjamin Button in Burbank, California.

We can't get over how good both Pitt and Angelina Jolie looked in their shades of gray at the Paris premiere of The Curious Case of Benjamin Button.

The Oklahoma native looked terrific in a tux at the 81st Annual Academy Awards.

Oui, oui! The Se7en stud looked lucky in love with then-girlfriend Angelina Jolie when they hit the red carpet for the Inglourious Basterds premiere during the 2009 Cannes Film Festival.

Pitt and then-girlfriend Angelina Jolie smoldered at the world premiere of The Tourist in New York City.

Sunglasses on the Golden Globes red carpet? Only if you're this hottie! 

Pitt was the fashion king of our dreams at the Orange British Academy Film Awards 2012.

If you think Pitt can't pull off a ponytail, please look back fondly at his 'do from the 12 Years a Slave premiere at the 2013 Toronto International Film Festival.

The Fury actor looked anything but furious at the 20th Annual Screen Actors Guild Awards. 

Hats and glasses and necklaces, oh my! The Big Short star was well accessorized at the 15th Annual AFI Awards in Beverly Hills.

Pitt was a mustachioed stud at the London premiere of Allied.

That stare! That 'do! That slightly unbuttoned shirt! Pitt was the epitome of not trying too hard at the 7th Annual Sean Penn & Friends HAITI RISING Gala Benefit in Hollywood.

The Ad Astra star was glowing at the 76th Venice Film Festival.

A three-piece suit at the 2020 Golden Globes? Be still, our hearts!

The Oscar winner subtly amped up a traditional tux by donning a velvet black jacket for the 92nd Annual Academy Awards.