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
Pitt was one of the main stars of this film from 1994, and it helped catapult him and the customer cowboy hat he wore to popular status. In fact, the natural dyed, pure beaver fur felt cowboy hat he wore in this movie is still popular and sought after today.
The cowboy movie hat has a brown felt teardrop crown and a four-inch brim. The pinched hat has a brim that curls up on the sides and in the back, The front of the brim dips down slightly. The Tristan cowboy hat also had one of those really cool western hatbands, which contrary to other reports online was not a braided leather or horse hair hat band.
J.D. From Thelma and Louise

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 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.

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.

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.

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.