You’ve seen it. That perfectly positioned, backwards-facing flat cap that seems to have its own SAG-AFTRA membership. It’s as much a part of the man as the word "motherf**ker" or those piercing stares he gives before a monologue. Samuel L. Jackson and his Kangol caps aren't just a celebrity endorsement. It's a love affair that’s spanned decades.
Honestly, it’s hard to imagine him on a red carpet or a golf course without one. But how did a British military beret company become the signature look for Hollywood’s highest-grossing actor?
The 1960s Spark
Most people assume Sam Jackson started wearing these hats in the '90s to look cool for Quentin Tarantino. Wrong.
It actually started way back in the 1960s. Jackson’s grandfather gave him his very first Kangol—a brown tweed number with a leather button. He was just a kid in Chattanooga, Tennessee, but that gift planted a seed. He wasn't trying to be a hip-hop icon yet; he was just a guy who liked traditional clothes. Corduroys. Tweeds. Collared shirts. He once described himself as a "misfit" because of how he dressed.
Fast forward a few decades and that one brown hat has turned into a collection of over 300.
The Jackie Brown Turning Point
If the '60s were the start, 1997 was the explosion. In Jackie Brown, Jackson played Ordell Robbie, a ponytail-wearing gun runner with a penchant for—you guessed it—Kangol caps.
He wore them backwards. It was a choice. That specific look, particularly with the Wool 504, became legendary overnight. It wasn't just a costume choice; Jackson kept wearing them after the cameras stopped rolling. He wore them to the Oscars. He wore them to interviews. He wore them to the grocery store.
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"The popularity of the cap really increases after this movie... he continues wearing it off the set. You can always see him wearing a variety of Kangol caps in interviews, out and about and in other films." - Miller Hats Historical Archive
504 vs. 507: What's the Difference?
If you're looking to grab one for yourself, you'll likely run into these two numbers. They look similar to the untrained eye, but they aren't the same.
The 504 is the OG. It was introduced in 1954 (hence the name) and has a wider, flatter profile. It’s the "classic" flat cap look.
The 507, on the other hand, is sleeker. It’s got a more ergonomic, curved fit that feels a bit more like a baseball cap. It’s narrower. If you have a smaller face or want something that looks a bit more "modern sport," the 507 is the go-to. Sam wears both, but the 504 is what he’s most famous for flipping backwards.
Materials Matter
- Wool: The heavy hitter for winter.
- Tropic Ventair: This is the one with the little holes. It’s breathable. Perfect for the golf course.
- Furgora: That fuzzy, angora-blend texture. It screams '90s hip-hop and big energy.
The Golf Connection
Samuel L. Jackson loves golf. Like, "it's-in-his-movie-contracts" loves golf. He literally has a clause that says he gets to play a certain number of times a week while filming.
Because of this, he eventually partnered with Kangol for a specific Kangol Golf by Samuel L. Jackson line. These weren't just random hats; they used his favorite colors—lots of purple and yellow—and featured his silhouette on the hangtags.
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He even did a "Motherfunder" crowdfunding video for the Bollman Hat Company (the folks who own Kangol now) to help move their production from China back to Pennsylvania. He did it for free. That's real loyalty.
Not Just a Brand, a Uniform
There is a specific psychology to why this works. In a world of flashy, ever-changing fashion, Jackson found a "uniform." It's reliable. It covers the head (Jackson has been bald for a long time and leans into it), and it provides a frame for his face that is instantly recognizable.
Kinda like Steve Jobs and the black turtleneck.
It also bridges a gap. Kangol has roots in the 1930s British military, but it was "raised" in the 1980s New York hip-hop scene by guys like LL Cool J and Grandmaster Flash. By the time Jackson took the reins, he was blending "Old World" prestige with "Street" credibility.
How to Wear It Without Looking Like You're Trying Too Hard
If you want to pull off the look, take a page from the man himself.
- Flip it: Wearing it backwards is the "Sam Jackson" way. It turns a traditional "old man" hat into something aggressive and cool.
- Size it right: These aren't "one size fits all." If it's too tight, you look like you're wearing a beanbag. Too loose, and it looks like a costume. Measure your head.
- Coordinate, don't match: You don't need a purple suit to wear a purple Kangol. Use the hat as the "pop" of color in an otherwise neutral outfit.
- Confidence is the main ingredient: You can't be shy in a Kangol. You have to own the room.
The Legacy of the Kangaroo
Despite the logo, Kangol isn't Australian. It's British. The "K" is for knitting, "ANG" is for angora, and "OL" is for wool. The kangaroo was only added in 1983 because Americans kept asking for "the kangaroo hat."
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Today, Samuel L. Jackson remains the unofficial—and sometimes official—face of the brand. Whether he’s at a Lakers game or a film premiere, the hat is there.
It’s a rare thing for a celebrity to be so tied to a single item of clothing without it feeling like a gimmick. With Sam, it just feels right. It's authentic. It's a part of the character he plays in real life: the coolest man in the room.
Get the Look
Start with a Tropic 504 Ventair in black or navy. It's the most versatile entry point. It works in the summer, keeps its shape, and doesn't feel too heavy. Once you get comfortable with that, you can move into the bolder colors or the fuzzy Furgora styles.
Just remember: brim to the back if you really want to channel the Ordell Robbie energy.
Stop by a dedicated hat shop rather than a general clothing store to get the sizing right. A proper fit makes the difference between "fashion statement" and "I found this in my uncle's closet." Once you have the fit, the rest is just swagger.
Next time you’re watching a Samuel L. Jackson marathon, keep an eye on the headwear. From the "Spitfire" to the "504," it’s a masterclass in how to build a personal brand one cap at a time.