Brad Pitt Cowboy Hats (with Photos)

Brad Pitt Tristan Cowboy Hat
(Clockwise) Brad Pitt straw cowboy hat in Thelma & Louise (Photo by MGM/Getty Images), Brad Pitt fishing hat in A River Runs Through It (Liaison/Getty Images) and Brad Pitt Tristan Cowboy Hat in Legends of the Fall (Sony Pictures)

As a member of Hollywood A-list, Brad Pitt has had a long and storied career. In his young days, he had bit parts on TV shows like Dallas and 21 Jump Street. Then, in 1991, he hit the mark with a small role as a young stud in Thelma and Louise. The world was never the same afterward. His Brad Pitt cowboy hat look was forever etched into motion picture folklore. So let’s dive deeper and explore all the headpieces he made fashionable. And let’s start with the mens cowboy hat style he made famous.

Tristan Ludlow From Legends of the Fall – The Brad Pitt Cowboy Hat

J.D. From Thelma and Louise

Brad Pitt Mens Straw Cowboy Hat, Thelma & Louise, 1991
Brad Pitt wearing a men’s straw cowboy hat in Thelma & Louise, 1991 (Photo by Metro-Goldwyn-Mayer/Getty Images)

The titular duo is on the run from the law when they meet Pitt’s character J.D. and spend the night with him. J.D. is a bit of a drifter and he makes money via armed robbery, but not in a bad way. 

In the film, Pitt wore a straw cowboy hat with a braided leather hatband. The band also had a tail, which you could see dangling a little from the back. The hat is a typical cowboy accessory, with a tall, pinched crown and a crease running through the center. The brim curves up on the sides and down in the front and back. 

Brad Pitt and Jennifer Aniston in a black felt trilby at the premiere of “The Bourne Identity” at Universal CityWalk in Los Angeles, Ca. Thursday, June 6, 2002. Photo by Kevin Winter/ImageDirect

Brad Pitt is a Man of Many Hats

Mr. Pitt looks good both on and off-screen, and he often wears hats when he’s out and about. Here’s a rundown of the various hats he’s worn through the years:

Mens Flat Cap – Pitt has worn this type of hat numerous times, including to the Beowulf premiere with his then-wife Angelina Jolie. This mens cap has a small, curved front brim and an angled, floppy crown. It resembles the type of hat worn at golf tournaments. 

Brad Pitt wearing a mens wool flat cap at Beowulf premiere
Brad Pitt wearing a mens wool flat cap and his wife Angelina Jolie at the Beowulf premiere, 2007 (Photo by Barry King/WireImage/Getty Images)

Trilby – A trilby is a classic hat style that fits with a classically handsome actor like Pitt. This straw trilby hat has a fixed, narrow or stingy brim (less than 2 inches). The crown has a center crease with a pinch in the front. Many people confuse trilbies with fedoras, but they are very different hat styles. 

Brad Pitt wearing a straw trilby hat at a premiere
Brad Pitt wearing a straw cowboy hat at the premiere of Full Frontal, 2002 (Photo by SGranitz/WireImage/Getty Images)

Top Hat – 2002 was a year of hats for Pitt, and he wore a straw top hat to that year’s Sundance festival. The hat had a tall, circular crown with a 2.5-inch upturned brim all the way around. At the time, he was married to Jennifer Aniston, and she often accompanied him and his hats at various red carpet events. 

Brad Pitt wearing a straw top hat at Sundance
Brad Pitt wearing a top hat at the Sundance Film Festival, 2002 (Photo by J. Vespa/WireImage/Getty Images)

The Hat Stops Here

Brad Pitt is a man of many styles and hats. The Brad Pitt cowboy hat is an iconic look, and this article dives deeper into what makes it work. Learn more about how Pitt’s hats have accentuated his natural features.

Red Brim Hats: In Praise of Artful Details

I was recently scrolling through fashion pictures looking for some new season inspiration when something stopped me.…

More →

Tom Ford Cowboy Hats: Pleasure Posse Saddles Up

It was a new fragrance debut, but it might as well have been a Tom Ford Cowboy…

More →
Pharrell Williams wearing three unique hat styles at various events

The Best Pharrell Williams Hat Fashion Guide

Few music producers are as versatile or as well-known as Pharrell Williams. However, outside of his musical…

More →
A mix of famous, well-known Johnny Depp hat styles

The Ultimate Johnny Depp Hat Style Guide

Acting is an inherently creative craft and one that some people embrace both on and off-screen. One…

More →

Strange New Street Style: Incredible Coachella Fringe Fest

After a two-year pandemic imposed hiatus, more than 125,000 music lovers, fans, and celebrities descended on Indio…

More →
A wide variety of hats made their appearance at Coachella 2022.

Perfect Festival – Cool Coachella Hats

The Coachella Valley Music and Arts Festival was founded by Paul Tollett and Rick Van Santen in…

More →
A wide variety of felt hats were seen at Coachella 2022.

The Best Coachella Outfit for Women with Hats

The return to Coachella in 2022 went above and beyond in terms of fashion. A “Let’s Get…

More →
The many hats of Jessica Alba include a Trilby, an Australian Outback, and a Floppy hat.

The Influential Hat Styles and Lifestyle of Jessica Alba

There is a certain level of allure in talking about Jessica Alba (born April 28, 1981). The…

More →