I knew Justin Timberlake had come a long way since his frosted tips teenie-bopper days. I don't mean musically which, of course, duh. I'm going in on the superficial stuff, like his hair and facial hair. But until I examined his various styles side by side, I had no idea how often he has changed in the last 20+ years, not to mention how frequently he reverts to some of his more classic styles (the less polarizing ones, that is), while still managing to tweak them and make them individual within his portfolio.

This might sound weird but, I never realized how faithful he was to maintaining a good-looking neck beard—you know, the transition part between the beard and the not-beard. I also didn't realize that I could become borderline infatuated with a well-faded neck beard. (Salute to you, Mr. Timberlake.) It's an elite move—much harder to maintain than a precisely-trimmed neckline. I encourage all aspiring beard-havers to rifle through Timberlake’s looks over the years: The first ones are purely for the record books (though his 1997 aesthetic is being revived, for better or worse, in Brooklyn, East London, and São Paulo right now). As for the later half of his career—the mid-aughts onward—observe the subtlety with which Timberlake changes this or that, how generous he is with the hair relaxers, and how big a difference it can all make.

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1993-ish: Shout out to all Mickey Mouse Club alums who made it, and to those who did not. Timberlake is pictured here with fellow Mouseketeer Ryan Gosling. This starting point should help you the scope of the appreciate the grooming journey you're about to witness, wherein Timberlake embraces and then rejects those once-signature curls.

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1997: Hard to believe this was just 4 years later, but here’s the *NSYNC Timberlake we all got to know in the late 90s. This haircut would actually work these days, highlights and all. (Don’t they say these things come back around every 20 years?) It’s great for prominently defining your natural texture—see how piece-y it is? If you’ve got curly hair, stock up on some curl-enhancing cream to give your style the same definition.

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1998: I don’t want to make the ramen-noodles reference, but we’ve all heard it, and this is why. The curls are longer, it’s dyed blonde instead of highlighted, and the lower half remains his natural dark blonde. The same curl-defining cream would help you here, but this style feels more dated than the last one. (A little length and color makes a huge difference.)

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1999: A year later, Timberlake brought everything to one even length, and went back to a more subtle highlighted look. Maybe it’s just the peroxide-blonde dye-job in the last one that was so off putting, because this one actually kind of flatters him. Kind of. Please now picture Young Justin in his dressing room with a blow dryer and diffuser—the hair-dryer extension that has teeth, which direct the hot air and help enhance curls. If you don’t have one, curly-haired men, consider getting one. It's better than time travel.

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2000: Same hair, new beard. Er, not a beard. Not even a goatee, really. This is kind of an island of fur just marooned on his face. It belongs in a vault with the shades.

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2000, part 2: 2000 wasn’t a shining year for JT. This look is extremely hard to pull off—especially when your hair is as textured and unruly as his. It starts to dwarf your head. Just keep everything on the shorter side if your curls match Justin’s. (1997 was really the only good year for this era.)

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2001: Early aughts celeb romance! Back when innocence was still possible. Sigh. Timberlake has returned to a natural state, hair-wise: His curls are grown uniformly, sans coloration. He’s got some nice shine up top, too. Perhaps there’s a pinch of hair oil going on.

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2002: This feels like the first glimpse of the modern Timberlake, at the start of his solo career. Gone are the curls, though he’s still got some texture in there. Talk to your barber or stylist if you want to straighten your own short hair (since a straightening wand is only good for longer hair). Chances are they’ll start you out with some relaxing oil, or a curl-reducing cream pomade if it’s long enough to comb through.

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2003: I never realized how often Timberlake changed things up in the first half of his career. In my head, he wore the late-90s curls for a decade or more. But no, here he is in the early aughts with a buzz and some weeklong stubble. Save for a little neck beard, it was a good change of pace as he carved his own identity.

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2004: At the Grammys, JT sported a Caesar cut, curl-free. His hair is short enough here that the curls wouldn’t be showing themselves, though those across the forehead might have been relaxed into place. (Negative points for the scraggl, overgrown neck beard, though.)

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2007: Jumping ahead a few years here, mostly because Timberlake didn’t change his style much for a while—it was always this buzz cut or something slightly grown out, typically with some stubble. (And a neck beard! I’m starting to appreciate it, since he’s been so dedicated to it.)

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2008: This, right here, is terrific. He’s got the Caesar, grown more than in 2004, and all relaxed. And, yep, I’m fully endeared to the un-manicured stubble.

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2009: The curls made a brief comeback in 2009, as did his bare face. It’s like 2001 all over again.

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2010: This is the first glimpse of Phase 3 JT—the guy we currently see. Long hair, probably straightened with a flat iron this time, since it’s seemingly long enough. (Then blown back with some cream pomade, or paste, applied to his towel-dried hair, is my best guess.) I think it looks especially sharp with his couple-weeks’ scruff.

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2011: This is where Timberlake gets our props as a grooming idol—he seamlessly switches between styles (and revisits them!), leaving me confused about what year it is. Never mind that this is seven years later, but this could very well be 2004 Justin.

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2013: AND he finds ways to look unique with a couple simple tweaks: Five o’cock shadow, medium-length straightened hair, styled this time more loosely—probably with a medium-hold cream, blown dry.

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2014: Here’s Timberlake touring his last album, The 20/20 Experience, with a nice fade (the first we’ve seen on him in this timeline, which seems odd) and a fuller-than-usual beard. Yet again—two small tweaks, one new look. It’s our favorite of the pack.

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2016: Here he’s got a high-and-tight fade, relaxed and texturized (probably with fiber, given it’s matte and too short for much else). It’s all a good match for the fuller beard, something most guys could pull off.

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2017: See what we mean about how he revisits styles often? Maybe the beard is fuller this time, but this longer, coifed style has resurfaced a handful of times this decade. (And rightfully!) I like that there’s some waviness to this iteration, too—his hair is relaxed, but not entirely. Maybe it’s settled a day or two, or his stylist went in with some texturizing putty.

Adam Hurly has been covering men's grooming since 2013 (and for GQ since 2016). He is also a travel writer. In Fall 2024, Adam is launching Blue Print by Adam Hurly, a men's grooming platform. Adam resides in Lisbon (previously Berlin, NYC, and San Francisco). He is a Sioux Falls, SD, native... Read moreWriterInstagramRelated Stories for GQJustin TimberlakeFacial HairHair