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Red Carpet Rebel: The Best Photos Of Brad Pitt Over The Years

Monica May 17, 2023

Perhaps the most recognized leading man in Hollywood for many years, Brad Pitt is considered one of the most successful celebrities in history. Pitt is the object of affection for generations of fans. But he’s not just all good looks alone. He’s won tons of accolades, including two British Academy Film Awards, the Academy Awards, a Primetime Emmy Award, and two Golden Globe Awards. Those are the achievements of many lifetimes.

Pitt has had tons of various roles throughout the decades. Many would argue his most notable movie was Fight Club, but he also starred in films like Troy, Thelma and Louise, Seven, Interview With A Vampire, Babylon, and Snatch. Through it all, Pitt was able to stay relevant and on top of the game by evolving his beloved style with the times. We chronicled just how dramatic Pitt’s looks have evolved over the years. It certainly paid off for the Missouri-born heartthrob. And to think he nearly completed a journalism degree instead of getting into acting.

Old School In Leather

Way back in 1988, Pitt went bigger than ever, with an oversized leather jacket that swallowed him whole. But he still rocked the baggy fit nonetheless. While most of us would look like we were wearing a trash bag, Pitt managed to make this worn-in bomber jacket look aesthetically pleasing (via GQ Magazine).

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The Yellow Vest

When Brad Pitt rocked this yellow vest in 1988, he looked like a surfer straight out of the Southern California ocean. He paired the vest with a bandana and black sunglasses that look at home on top of his head. Even though we don’t come close to having the guns that Brad Pitt shows off with this vest, we’re certainly inspired by the look (via GQ Magazine).

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Young Pitt In A Mullet

While most of us want to hide the photos from our youth, Pitt can show his off. In 1989, a young Brad Pitt was young and in the early days of his acting career. His hair matches his full-bodied personality at the time. He rocked a mullet, paired it with a leather jacket, and made it look bountiful (via Men’s Health).

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The Beach Look

Once the mullets went out of style, Pitt decided to change up his look and went for a messier, spiker style in 1990. His bangs curve perfectly in front of his eyes. He pulls off a sensual look for the camera that makes most of us melt in our seats (via Men’s Health).

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Double Up On Denim

The ’90s were all about denim, especially in 1991. During this red carpet appearance, Pitt doubled up on denim with a jean jacket and jeans. But he didn’t let the jackets stop there, he tied the knot of his look with an oversized jacket, thrown on top of his clothes, and a stylish pair of glasses. If any of us tried to pull this look off, we’d look like complete fools, but he made it work and work well (via GQ Magazine).

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The DB Suit

In 1991, Brad Pitt rocked this DB suit many of us never knew we needed. In this style in the early ’90s, he took fashion to another level. We see a boxy, louche fit, wide-notch labels, and a floral printed tie to top it off and add a splash of color. This is a style we could undoubtedly bring back (via GQ Magazine).

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On The Streets With A Power Tie

Brad Pitt walked the streets with Juliette Lewis in 1992 with a power tie, perfectly paired with a suit. On his way to the Spirit Awards, he’s seen strutting with a double-breasted suit and a baggy jacket. His high-wasted trousers accent the suit. To give his outfit that extra pop, he paired it with a power tie that can be seen from miles away (via GQ Magazine).

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Suede Is Back

Pitt pulls off every single style without having to try. Usually, we look good in a couple of styles and manage to nail the look. But Pitt nails every single look and leaves us all in the dust. In 1993, he brought suede back. He completed the look with a long-sleeved white shirt and gray pants. His long, elegant locks rest neatly on his shoulders. He looks like someone out of a movie…because he is (via GQ Magazine).

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The Bright Patterned Shirt

Brad Pitt didn’t only rock suede in 1993. It was also the year of bright-colored shirts. It’s the complete opposite of suede though the actor looks top-notch in both. Because the actor grew out his hair, it made him stand out from the rest of the crowd. This is the year he filmed the movies Legends of the Fall and Interview with the Vampire with a style that inspires a lot of us to try out but will likely fail at (via Men’s Health).

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Spiky and Sexy

Brad Pitt chopped off his hair and in 1995, he showed up to the Annual Golden Globes with a hairstyle that made him look unrecognizable. He rocks the short hair just as much as he rocked the long hair, even if we might miss his long locks (via Men’s Health).

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The Leather Coat

Pitt rocked this long leather coat in 1997. Without even having to try, he proved that you can pull any style off. Sure, we love a battered, vintage, leather jacket that makes us look like we’re part of a motorcycle gang. He surely looks like someone who was in Fight Club in this photo. It’s time to head to the thrift store and buy a Bratt Pitt-inspired leather jacket (via GQ Magazine).

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Open Collar

What’s wrong with an open collar, especially if Brad Pitt is rocking it? In 1997, Pitt went from a leather jacket to the open collar look. He opted for a slimming gray suit that suits his figure perfectly. He unbuttoned the shirt to make his style pop. This look makes people’s heads turn, though they turn for all the right reasons. He completed the look with leather boots and a big smile (via GQ Magazine).

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Matching Look

Brad Pitt took many liberties with his style in 1997. He went from leather, to open collar, to matching his girlfriend. Pitt and Gwyneth Paltrow were mocked for having the same haircut, though we’re not sure who rocks it better. They both pull it off. We’re sure you can’t say that about most people who accidentally match their partner’s hairstyle (via Men’s Health).

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All In White

Who knew 1998 was all about white? Brad Pitt. He took his whites and layered them to near perfection. When cold weather is on its way, the best thing to do is add those layers to one another to prevent that inevitable frosty chill. But it doesn’t end there, Pitt also added a bit of denim flair to complete his already complete look (via GQ Magazine).

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Micro Shades

We usually throw on a pair of micro shades when we’re trying to make our friends laugh. But in 1999, Pitt grabbed a pair of micro shades and rocked them. 1999 was the year of The Matrix, and even though Brad Pitt didn’t star in the film, he made it look like he did. For a maximum look, he topped the shades off with a completely black outfit. In the photo, he’s even flicking his wrist like he owns the place. Maybe he does (via GQ Magazine).

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Back To Brunette

Brad Pitt took back his blonde hair and brought back his brunette. At the American Film Institute in 2000, Pitt waltzed in with dark hair that surprised everyone. But he didn’t dye it because he felt like it, he dyed it for the film Snatch. Either way, this guy can pull off any clothing style and hair color (via Men’s Health).

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Back To Blonde

The brunette hairstyle didn’t last very long, because Brad Pitt changed up his hair color again in 2000 and turned back to blonde. At the Erin Brockovich premiere, he sported his new do with a stylish middle part and highlights that perfectly accent his blue eyes (via Men’s Health).

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Switch It Up

In 2001, the actor went shorter than ever before with a buzzcut hairstyle. It looks great with his neutral-colored suit. It’s a stark contrast to the long locks we saw nearly a decade ago. But with time, people change, and as we’ve learned, Pitt can pull off any change (via Men’s Health).

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The Helmet Hairstyle

Nothing screams more than the 2000s with this helmet hairstyle. In 2002, Pitt styled his hair with tousled bangs and a layered cut that give him a beachy look. Considering he doesn’t have a consistent style, this look suits his face. We’re not surprised by the Brad Pitt look anymore (via Men’s Health).

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The Beard

If you thought Brad Pitt couldn’t pull off a beard, think again. In 2002, he surprised us with this huge beard and goatee that seemed to come out of nowhere. He brought the helmet hairstyle to another level with this giant beard on his face. If anyone’s going to show up on the red carpet with a giant beard, it’s Brad Pitt (via Men’s Health).

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The Button-Up Shirt

In 2003, Brad Pitt ditched baggy jeans and instead sported a button-up shirt with a geometric pattern. He has a stylish pair of sunglasses and his long hair to complete the look. We can all agree that his jeans just scream the early 2000s (via Hola).

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The Flat Cap

In the early 2000s, Pitt sported a flat cap while holding one of his young children. The actor has a total of six kids, three of which are biological, and the other three are adopted. Their names are Pax, Maddox, Zahara, Vivienne, Shiloh, and Knox. His three adopted children are from Ethiopia, Vietnam, and Cambodia. This adorable photo showcases Pitt not only in style but as a loving father (via The List Wire).

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Beach Blonde Babe

In 2005, Pitt starred in Mr. and Mrs. Smith. And with that came a change in hairstyle. He dyed his hair beach blonde. While most of us would look like a cheesy Barbie doll, Pitt pulled it off. He even topped it off with yet another leather jacket. His hair wasn’t the only thing that changed that year, it was also his divorce with Aniston (via Men’s Health).

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From Blonde To Gray

Pitt wasn’t turning gray, but he did have to dye his hair for his role in Babel. The dusty style looks good on the star. We’re beginning to believe that Pitt would even look good with red or purple hair considering he pulls off anything and everything (via Men’s Health).

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Tailored Suit

In 2006, Pitt took it a step further on the red carpet as the Meet Joe Black star. He looks sophisticated and well put together in this suit, which is a stark contrast from the earlier, baggier styles we saw in the 90s. We can see how Pitt is slowly maturing (via Hola).

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Holy Curls

Not only did Pitt sport a tailored suit in 2006, but he also had a head full of curls. The messy style looks good on his head, and paired with a suit, he looks like a model. Even though he did do a bit of modeling in the past but instead focused on acting, the star can certainly do anything (via Men’s Health).

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A Darker Look

1997 wasn’t the only year Pitt matched his girlfriend’s hairstyle. In 2006, we see another moment where he changed up his look to match his lover’s. Angelina Jolie and Pitt were spotted with the same hairstyle. He went for a darker look as Jolie tried out her naturally blonde hair (via Mirror).

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The Bangs

If anyone’s going to wear side-swept bangs, it’s Brad Pitt in 2008. At the Critics Choice Awards, the star wears this bedhead like he’s a professional. We’ve tried to sport the bedhead look, but we end up looking unkempt and untidy. At least Pitt managed to rock this style without trying too hard (via Men’s Health).

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Suede Is Back

It took Pitt nearly a decade, but he brought suede back in 2008. He paired the jacket with a crisp white shirt and plaid gray pants. His hair is combed back to perfection, and his sunglasses perfectly accent the colors in his outfit. The Inglorious Bastards star keeps surprising us time and time again (via Hola).

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The Cream Colored Suit

What would you do if you saw Pitt walking into a room wearing this? We would melt to the floor. This cream-colored suit, paired with aviators, a scarf, and two-toned shoes made Pitt look like the most handsome man alive in 2008. We never thought we’d see a man going from a baggy bomber jacket in the early 1990s to a sophisticated and sexy look, but if anyone’s going to do it, it’s going to be Pitt (via Hola).

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The Gray Goatee

In 2009, Pitt wasn’t afraid to show off his age. He wore a gray goatee that was perfectly shaped on his face. His hair was short and simple, and he wore a neutral shirt to make his goatee stand out (via Men’s Health).

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The Loose Beanie

Most of us wear loose beanies when we’re hungover and trying to hide our messy hair. Brad Pitt uses it to this advantage. He was spotted at a football game in 2010 in hipster-styled clothes with a leather jacket and beard for added touches (via Hola).

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The Quiff

Pitt didn’t only sport a beanie in 2010, but also a quiff. It’s a neat style that let his elegance shine through. Even though it’s not on par with an Elvis Presley quiff, he brought it back but gave it a Pitt-styled spin (via GQ Magazine).

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Sideburns

In 2010, to add to his hipster, quiff look, Pitt changed up his hairstyle and tried out sideburns for the first time in his life. Even he can pull off a look that many men could never wear. There’s so much potential in his sideburns that no one knew about. Maybe it’ll inspire you to grow out your sideburns, though we wouldn’t get our hopes up (via Men’s Health).

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Ombré

To take it to another level, Pitt went from sideburns to ombré in 2011. He tested out his hair trends another time and made his hair light blonde at the tips and darker at the roots. While most people need to try out different styles to find one that suits them, Pitt tries out every style because they all suit him (via Men’s Health).

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The Classic Look

Pitt can pull off any clothing and hairstyle. But he can also pull off one of the simplest looks, a black suit, and tie. This 2012 combo is sophisticated and tidy, and though we’ve seen Pitt with long hair and brightly colored shirts, we all have to agree he looks the best in a suit (via Hola).

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The Army Cut

Pitt starred in the movie Fury. In 2014, many people sported the army cut, with short backs and sides in the United Kingdom. Pitt likely influences this hairstyle, though he’s the only one who could ever truly pull it off (via GQ Magazine).

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The Fury Era

The Fury era brought a lot of changes to Pitt’s style. In 2014, he took plaid to another level, with a blazer and checkered shirt. He paired it with jeans to give it a simple, easygoing, yet elegant look. Is there anything Pitt can’t wear? (via Hola).

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Boyband Curtains

In one year, Pitt went from army cut to curtain bangs. There’s no one else in the world who could change up his style so drastically and still look handsome. In 2015, he showed up to the premiere of The Big Short in New York City wearing these boyband curtains, paired with a suit and sunglasses (via GQ Magazine).

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Polished With Jolie

We’re seeing yet another instance when Pitt mimicked his partner’s style. Maybe he finds more inspiration from his partner’s than we think. In 2015 at the American Film Institute Festival, he sported a hairdo that matched his wife’s. We don’t hate it at all (via Men’s Health).

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Suede Is Back

Pitt never let suede get away from him. In 2016, he brought the suede boots back and paired them with tapered jeans and a button-up shirt. This was the era of Seven, and Pitt made sure everyone knew it. He paired the jeans with a fedora hat, leather bag, and light sunglasses that made everyone’s hearts melt (via Hola).

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From Curtains To Spikes

It took Pitt two years, but the star went from boyband curtains to spiky hair. In 2017, he took his spikes half an inch higher and wore a neutral suit to match. His barely noticeable scruff looks good with the spikes (via GQ Magazine).

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Tan From Head To Toe

In 2019, the Once Upon a Time in Hollywood star wore a completely tan outfit with tan shoes to match. If anyone other than Pitt tried to pull this off, they would look ridiculous. He took monochrome and made it look cool (via Hola).

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Simply Brad Pitt

Pitt is slowly going back to his roots. In 2019, he wore his hair in a middle-length style, which probably suits his personality the best. Even though we love some of his outlandish hair and clothing styles, this one suits him the best (via Men’s Health).

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Suit And Tie

In 2020, Pitt wore yet another classic suit. We see his sartorial elegance in this simple outfit one more time, with a white shirt and bowtie to match. Alright, Pitt, we get it. You can wear anything and make it look good. Throughout the years, Pitt has done nothing but prove he can pull off any clothing style and hairstyle and look good doing it. It’s a feat most of us will never achieve, so we’ll just have to keep admiring Pitt for his ability to look good anywhere at anytime (via Hola).

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