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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).
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).