The Five Most Important LL Cool J Hats

Step into a world of LL Cool J’s hats.
Photos: MTV Style

LL Cool J will three-peat as Grammys host on Sunday, and we’re big-time pumped to see a perfect melange of pearly whites, charm, lip licking, and eye twinkles. (Ladies Love Cool James for a reason.) As far as his wardrobe choices go, there is one department in which he WILL NOT FAIL: That dude will wear a damn hat. We bet you one million dollars.

The simple fact is that LL Cool J and hats belong together. They’ve been in a long-lasting, loving, nourishing relationship since he was a kid. When he became a sensation with the release of Radio in 1985, it wasn’t long before he became synonymous with the Kangol bucket hat and transformed the accessory into a hip-hop essential.

Because of this attachment to his Kangol, there was a time in the late ’80s and early ’90s when LL Cool J’s bare head was basically a mythical creature, and people even started to wonder if everything was OK under there. I remember being so intrigued by what secrets lay under that brim. In the video for “Flava In Ya Ear (Remix),” the world got its big reveal: LL’s bald noggin peeking through the top of a leather visor. He glances coyly at the camera and brushes the surface, acknowledging the shift in what the world knew about LL Cool J’s head.

LL Cool J: a man of many hats.
Photos: Getty Images

Still, the man is rarely seen without a cap. Do an image search—the only time James doesn’t wear a hat is on NCIS: Los Angeles. (Actor Cool J = sans hat.) As a musician, it was a savvy move for him to create this association with an accessory. Not only did he succeed in looking cool, but with the Kangol he created a signature look that will go down as one of the best and most memorable hip-hop silhouettes of all time.

LL wears a lot of hats: father, actor, host, author… just kidding. We’re here to talk about literal hats; let’s save his metaphorical hats for another day or maybe never. In LL Cool J’s vast collection of headwear, there are five styles that stand out above the rest as Cool J favorites and cultural influencers. Let’s take a look.


Rockin dem beige beanies
Photo: Getty Images

James is going through a real beanie phase in his dad years. He’d wear ’em sometimes in earlier days but for a similar look, would gravitate more toward do-rags or bandanas. These days, the beanie is one of his top hats of choice and can be spotted primarily in “casual cool James” scenarios such as talk show appearances and low-to-medium fancy events. Maybe one day he realized how warm casino online a beanie can truly be and has not veered far from that coziness since.

Cool arms, LL.
Photo: Getty Images


LL at the ’91 VMAs
Photo: Getty Images

No other rapper wore a floppy top hat—a trend in the early ’90s—quite like LL Cool J. He grew so enamored with the look that he added a few dozen to his collection, and for a couple of years it became his new signature. In the long run, the hat failed to stick around, but it still stands out as one of LL’s most iconic looks.

That’s so ’90s.
Photo: Getty Images


LL in 2002
Photo: Getty Images

James’ go-to fancy cap has been a perennial favorite since the 2000s, when he started wearing them with increasing frequency—signaling a shift from his youthful street fashion sensibility to a more-sophisticated wardrobe. These days, it’s one of his top two most-worn hats. You can bet if he’s attending a black tie affair, LL’s suit of choice will be topped with an accompanying flat cap.

LL Cool J at the Grammys in 2013
Photo: Getty Images


Mariah & LL at the ’97 VMAs
Photo: Getty Images

When contemporary LL puts a fitted on his head, he means business. He wants results, and he wants them NOW. As a performance accessory, it unleashes extra reign and terror upon the masses in ways that a beanie simply cannot. With a backwards cap and mic in hand, LL reaches higher levels of rawness and seeeeeex appeal. And when it became his look of choice in the mid-’90s, he helped the often layered do-rag cap combo become ubiquitous.

I’ll tap into that conversation for a dollar
Video: Island Def Jam; GIF: MTV Style

LL does ’TRL,’ but he thinks it’s The Gun Show
Photo: Getty Images

Establishing dominance in ’Hit ’Em High’ music video
Video: Atlantic Records; GIF: MTV Style


1985. VV important image.
Photo: Getty Images

In the universe of celebrities and synonymous accessories, LL Cool J and Kangol rank with the greatest of them all. When Radio was released in 1985, there he was on the back cover with OG Air Jordan 1s and a red Kangol bucket. The style remained a permanent part of his image (in various bucket hat forms) until maaaaaaaybe 1990. Other artists favored bucket hats as well (Russell Simmons, for one), but it was LL Cool J who brought the Kangol to massive mainstream heights—and decades later, the hat represents an era in rap history.

In London, 1986
Photo: Getty Images

This was a necessary addition.
Photo: Getty Images

And if ya didn’t know, now ya know.

Ya bish!
Video: Island Def Jam; GIF: MTV Style

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