Justin Timberlake Is A Hat Man

A long, winding history of the pop star’s taste in headgear

There are men who like hats, and then there is Justin Timberlake, whose patronus is a hat.

Surely this is information you already know. When we explored JT’s perennial status as pop culture’s Ultimate Dad™, we acknowledged his zest for fedoras, newsboy caps, and, shit, even vests. But until he showed up wearing a chapeau in support of wife Jessica Biel’s turn in The Book of Love last weekend, I don’t think any of us really got what hats mean to Justin, or what Justin might mean to them.

Here’s Mr. Timberlake’s long, winding history of hats through time — and most importantly, what it all means.

1998–1999: The hatless years

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The Debut

Upon *NSYNC’s emergence as the boy band du jour (step aside, BSB), Justin’s head had no reason to hide. His curls were tight, his tips were light yellow, and his roots provided a delightful contrast, which explains why the rare sightings of our boy in a toque from this era tend to involve a concerned expression. On these occasions he looked as though he didn’t know why he was wearing it — or, perhaps, as though he didn’t know why wearing it felt so right.

2000: The handkerchief

Jeff Kravitz/FilmMagic, Inc

The Handkerchief

I know this isn’t a hat. But it’s a head covering that failed to do its job, because we were all still able to see JT’s cornrows. Which brings me to my first real theory: Justin may secretly be wearing cornrows every time he wears a hat today.

2000: The baseball fan


The Baseball Cap

You’ll be hard-pressed to find a photo of Justin squashing his glorious curls between the years 1998 and 2001. But for a rare moment, prior to a charity basketball game, he advertised his athleticism with a cap that was less tied to a particular basketball team and more tied to his future: one in which he’s tethered to snuffing out his natural volume.

2001: The denim cowboy

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The Denim Cowboy

And so we began to see the legacy of JT as a boyband member slowly dissolve. Instead of coordinating with his musical group, he showed up to the 2001s AMAs in matching denim with then-girlfriend Britney Spears. And while we thankfully never saw the return of yee-haw chic to his wardrobe, it did usher in the dawn of a new, post-*NSYNC reality, one that births the theory that Justin’s hats are dependent on his romantic partner. Which I can back up with the fact that when dating Spears, Timberlake only ventured down two very specific hat paths: baseball caps and a few more toques. Tellingly, no fedoras.

2002: Fedoratown

Kevin Winter/Getty Images/Fox


Ding dong, *NSYNC is gone. And while JT’s appearance at the 2002 Teen Choice Awards took place alongside a bucket hat–wearing Chasez, that same year ushered in a solo Timberlake, one free of his bandmates and of Ms. Spears alike. Justin’s new partner in crime? A flair for chapeaus, but especially one style thereof. From 2002 onward, Timby clung to the fedora like a lover he felt really, truly understood him. Which brings two more theories into the mix: Either he has been in a relationship with the fedora for nearly 15 years, or the fedora is the security blanket he clings to in moments of need.

I mean really.


2002 MTV Video Music Awards - Arrivals


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2002 Billboard Music Awards - Arrivals

(Also: #why)

I’m serious.

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Nickelodeon's 16th Annual Kids' Choice Awards - Arrivals

Minus a few wild cards.

James Devaney/WireImage


But what’s interesting is that while he’d throw a beanie or baseball hat into the mix, Justin never truly jettisoned the fedora upon evolving into his "SexyBack" self. Before 2002, his hats reflected the type of person he wanted to be seen as. As *NSYNC’s lead, he was hatless and fancy-free. As Britney’s boyfriend, he followed her accessories style. And once he was truly out on his own, he shaved off his curls and picked up a hat previously reserved for Frank Sinatra and our grandpas — years before it became mainstream again (meaning he was trying to evoke old Hollywood glamour, or at least his understanding of it). And he never let it go. Whether performing on SNL in 2006 or standing near a fancy painting in 2013, he adapted his look to suit his headgear. He refined his fedoras to work with his jacket, or adopted an earth tone to keep them casual.

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Fedora on SNL!

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Fedora Art

Which is even more interesting when you consider that he’s begun to straighten his hair and commit to full grownup-dad vibes — a look he combined with, yes, a fedora, even when receiving a Moon Man three years ago.

Larry Busacca/Getty Images for MTV

2013 MTV Video Music Awards - Show

Which tells me that Justin’s state of being is less about hats in general, and more about a specific style. Yes, we’ve seen him in a small variety of chapeaus over the course of his solo stardom, but his penchant for fedoras is arguably in no way about fashion (since they are the worst) and more about familiarity. Upon the end of *NSYNC and his relationship with Spears, Timberlake had but one thing: his fedora. And while he dabbled in newsboy caps and the occasional beanie, his flair for wearing a fedora implies that it’s his aesthetic teddy bear; it’s something he feels he needs and he clings to, whether he's taking a backseat to his wife’s movie work (like last weekend) or performing a song for and about Trolls, a movie that’s been advertised since most of us were middle-schoolers.

And yes, it’s tempting to think that underneath the fedora hides a secret. It’s easy to tell ourselves that beneath his go-to accessory he is a balding man, or he’s returned to secretly gel-scrunching, or that he’s reverting to his long history of iced tips. It’s easier still to believe the hat is his gateway to artistic integrity; that by wearing it, he will always know he is Justin Timberlake, solo star, and he is strong — like the headwear equivalent of Samson’s hair.

But it’s not. If years of watching Forensic Files have taught me anything (and believe me, they have), it’s that the answer I like the best is the most correct one. And I like the idea of Justin Timberlake eyeing his collection of hats and choosing the one that brings him the most joy. I like the idea of him holding one as he falls asleep, or turning the car around mid–road trip because he forgot the one that means the most. I like the mental picture of him trying a new fedora on in the mirror, remembering the feelings behind his first solo single, and nodding to himself in satisfaction.

He tilts it slightly, eyes himself adorned by his favorite sartorial constant, and, despite Jessica Biel’s cries that he please wear something else, he smiles and says softly, “It’s gonna be me.”

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