1988
At the Red Heat (we don’t remember it either), Pitt successfully played the cool-guy-not-trying-too-hard card in a distressed leather jacket and loose pants.
1994
The star channeled his inner Kurt Cobain with this (then) of-the-moment grunge look at the Legends of the Fall premiere.
1996
Shawl collar sweaters and corduroy pants were just as stylish together in 1996 as they are today.
1998
Pitt offset his sleek gray suit with some rebel grooming moves (spiky hair, scruffy goatee) at the Meet Joe Black premiere.
2000
Hollywood’s golden couple dressed the part at that year’s Vanity Fair Oscars party.
2001
Pitt was onto monochromatic outfits long before Yeezy brought it to the menswear’s mainstream.
2002
Based on this swag-tastic ‘70s-inspired outfit that could have been plucked out of Three Days of the Condor, we’re going to assume that Pitt is a big Redford fan.
2004
Proof you can never go wrong with a tonal navy fit: Pitt’s bundled-up look at the Along Came Polly premiere.
2004
All black doesn’t have to be basic, it can also be very badass as Pitt proved at the premiere of Troy.
2004
A real movie star should be able to wear the hell out of a tuxedo. Brad Pitt wears the hell out of a tuxedo.
2005
If you’re looking for proof that Brad Pitt is a man of extreme confidence, look no further. The A-lister rolled up to his Mr. and Mrs. Smith premiere in a worn Neil Barrett leather jacket, beat-up jeans, and freshly-bleached hair.
2006
Pitt perfected slim cargos and patterned short-sleeve button-ups long before we were telling guys to add them to their wardrobes.
2006
A properly tailored charcoal suit is the workhorse of any modern man’s wardrobe. Exhibit A: Pitt at 2006’s Babel premiere.
2007
There are probably ten men alive today who can pull off an ivory linen three-piece suit and Brad Pitt is one of them.
2007
Who ever sad all dad style was bad style? Certainly not us.
2007
Charcoal suit as workhorse wardrobe essential, Exhibit B.
2007
At a Venice Film Festival screening of The Assassination of Jesse James by the Coward Robert Ford, Pitt went full-tilt Bond in a crisp white dinner jacket.
2007
When you’re one-half of the world’s most-famous Hollywood couple, this is exactly how you should turn up to a Cannes red carpet.
2007
Yes, sometimes all you need to be the best-dressed guy in the room is a really great topcoat.
2007
Pitt’s predilection for driving caps and really great leather jackets was on display at the L.A. premiere of Beowulf.
2008
Who needs a tie when you can throw a scarf around your neck and ace that whole “rakish fella” look like Pitt did at the Critics’ Choice Awards?
2008
Pitt wore a dove gray three-piece suit at the Santa Barbara International Film Festival the way most guys wear a T-shirt and jeans.
2008
If you don’t want to wear a proper sportcoat to an event, follow Pitt’s lead at the 2008 Independent Spirit Awards and opt for a jacket in a luxe suede.
2008
How to be a gentleman with your wardrobe Part 1: When your partner should be the focus, opt for a quietly elegant (but totally unimpeachable) suit in a neutral hue.
2008
Did we mention that Pitt is kind of an expert at wearing tuxedos?
2008
Brad Pitt’s head of hair tends to get all the attention when we talk about the movie star’s grooming, but you can’t overlook that this guy knows how to rock a proper ‘stache when he wants to.
2009
Charcoal suit as workhorse wardrobe essential, Exhibit C (at the premiere of The Curious Case of Benjamin Button)
2009
When you’ve got a good thing going with your go-to fit, there’s no need to mess with it (but you can add a pair of classic shades if you want).
2009
Pitt + a Tom Ford tuxedo = sartorial success, every time—and especially at the 2009 Academy Awards.
2009
Back to black—all of it—at the L.A. premiere of Inglourious Basterds…
2009
…and in a white-out look at the premiere of The Time Traveler's Wife.
2010
At the L.A. premiere of Salt, Pitt harnesses the power of man jewelry with one simple chain and minimal pendant.
2010
The shearling overcoat Pitt wore to the NYC premiere of The Tourist would make even Jon Snow jealous.
2011
Most famous guys would get our disapproval for sporting shades with a tux on the red carpet. But on Pitt, the gradient lenses only add to his ultimate leading man appeal.
2011
Even in amber-hued lenses at Cannes’ Tree of Life screening (with costar Jessica Chastain), Pitt still looked great.
2011
This is wear Pitt hit inhuman status. No man alive should look good in a top-to-toe outfit best be described as “flesh-colored,” and yet, somehow, Pitt still looks effortlessly stylish.
2011
On The Tree of Life red carpet, Pitt reminded us you can wear a suit and still be the coolest guy in the room.
2011
Another big time movie premiere, another A+ gray suit for Pitt.
2011
If it ain’t broke, why fix it? And there’s nothing about this three-piece navy suit (with requisite shades) Pitt wore to the Moneyball premiere that needs fixing.
2011
Pitt went with monochromatic blues and Buddy Holly-esque eyewear for the win at the In the Land of Blood and Honey premiere.
2011
Pitt actually needed the cane here following an injury, but even if he didn’t, we’d still be on board with his accessory choice.
2012
Casualwear need not look sloppy, as Pitt’s black hoodie and V-neck illustrate here.
2012
It’s doesn’t get much better than Pitt wearing a Gucci tux and topcoat at the 2012 BAFTAs does it? We’ll answer that for you: No, no it does not.
2012
If you have a black tie event coming up, save this photo, print it out, and bring it to your tailor. He’ll know what to do next.
2012
At Cannes for Killing Them Softly, Pitt shows guys everyone the proper way to make their go-to suit summer-ready.
2013
There’s not much (if anything) that doesn’t work for the former Mr. Angelina Jolie, but all-black and aviators works very well.
2014
Everything about this photo is slick. Pitt’s tux is about as slick and slick gets, his hair is slicked back the right way, and the power couple manages the one thing most other duos can’t: dressing alike without forcing us into an endless eye roll.
2016
Variations of this all-white look have been Pitt’s go-to in 2016—he wore it three times in one week. You have to admire the guy for keeping it simple, no matter how messy life gets.
2016
If you're not going to drive a car in the elite 24 Hours of Le Mons race, you should stand on the sidelines and win style points in a zippered suede Tom Ford jacket and distressed denim.
2016
At the Spain premiere of Allied, Pitt once again nailed debonair in a navy suit, this time paired with a Salvatore Ferragamo coat and patterned scarf.
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