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Charting Harry Styles's Journey to Manhood, One Weird Hat At A Time

Anne T. Donahue on the stages of teen pop masculinity.

Between the Grammys, NME Awards, and the upcoming Brits, we’re clearly in the midst of a culturally and aesthetically rich era — especially in terms of the looks worn by young men in pop.

Not that any of it is original. Since The Beatles emerged in their coordinated suits, since Mick and Keith forfeited shirt buttons for skin, and since Marky Mark rejected sleeves in general, young men with something to prove have used style to underscore their musical identity, adding to their mystique (or lack thereof) by asserting who they are through what they’re wearing.

And right now this move’s more obvious than ever. On his recent GQ cover, Justin Bieber pouts in prints -- two types of polka dots worn with tweed -- as he poses with a pocket square as visible as his watch, all while showing off three rings that allude to the notion of power and money. So, according to his clothes, Justin Bieber is a boss (maybe even an old-school “gangster”), despite him only just escaping the hole he dug for himself in 2013 and 2014.

Of course, J-Biebs isn’t the only one aesthetically fronting. The stylistic stages of an early-to-mid-twenties pop star tend to do one of two things: (1) establish the wearer as a grown-ass man and/or as a musician who’s finally arrived, or (2) confirm that the thirst is real and that, like the rest of us, he will regret his choices thoroughly. Here’s how to make sense of what.

1. PLUNGING NECKLINES

As seen on: Harry Styles

One Direction progressed, and so did Harry Styles’s neckline. Which, when you realize he’s simply following in the style footsteps of Joe Perry, Mick Jagger, and Keith Richards, is hard to truly condemn -- especially since Harry’s tops tend to be exclusively Saint Laurent or Marc Jacobs. It also sends a message: I’m a not a corny teen icon, I am a real artist. Look at my navel. When looking at the rest of 1D, we notice they opt to wear their shirts traditionally: as T-shirts, as hoodies, or done up to an acceptable point, the way god/the designer intended.

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Will he live to regret it? Designer credibility aside, we’ll always think of this look as “those few years Harry didn’t button his shirts up.”

2. SLEEK SUITS

As seen on: Justin Bieber, Harry Styles, The Weeknd

When Justin Timberlake donned a suit on the album cover for FutureSex/LoveSounds, he asserted his post-boy-band adulthood. Such is the point of such a traditional look: It makes sense that, as a young man desperate to establish himself as an artist who’d never egg his neighbor’s house, Bieber would appear in a suit not just on the cover of a magazine but also on the Grammy red carpet (and in Saint Laurent, no less).

Meanwhile, Harry’s approach is different: Not only has Harry been seen almost exclusively in Gucci suits (if he's wearing a suit), he wears them traditionally: buttoned to the top, fitted, and runway-appropriate. So where Bieber uses a suit to assert maturity and finesse, Harry demonstrates his understanding of technique, proving that he can dress up and wear a piece in a way that does it justice (before catering to his current penchant for exhibitionism). He's wearing them like Timberlake, but is more likely to score a label campaign or collaboration.

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Will they live to regret it? Suits are safe.

3. STATEMENT PANTS

As seen on: Ed Sheeran, Louis Tomlinson, Nick Jonas

Webster’s Dictionary defines “statement pants” as -- just kidding! But where the safe bet for dude-centric bottoms had been limited to drop-crotch skinny jeans, the last few months have seen leather counterparts, oversize joggers, and, in the case of Ed Sheeran, casual capris.

Last year, leather sweatpants were a quick and easy way to assert one’s investment in current trends. (See: Kanye’s embrace of the look, as well as Usher’s, Future’s, John Legend’s.) So when Nick Jonas wore a leather suit to last year’s VMAs, it spoke of confidence, adulthood, and moreover, relevance.

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Will they live to regret it? Nothing establishes era and personal ethos like a pair of pants. But at the same time, pants are a safe way to experiment since -- unless they’re capris -- they're never bad enough to truly ruin a person.

4. UNDERDRESSED

As seen on: Zayn Malik, Shawn Mendes

There are two schools of underdress. Back in the early 1990s, the artist formerly known as Marky Mark capitalized on his Calvin Klein underwear deal to telegraph DGAF comfort, a sure sign of masculinity. And Louis, the current resident bad boy, is trying hard to convey the same thing.

But this year, we’re seeing something a little different. On the one hand, we have Zayn, who showed up to a Grammy pre-party in an untucked, unironed dress shirt with rolled-up sleeves. Which is pretty standard, since his current M.O. is to swap out his former 1D uniform for T-shirts, leather jackets, or a complete lack of top. To have dressed up more would’ve signaled a loyalty to his former self, the idea that he gives a shit, and since not enough distance exists for him to acknowledge it, he’s erring on the side of righteously underdressed.

Meanwhile, Shawn Mendes’s gravitation to jeans, a simple T-shirt, or a basic sweater sees him also err on the side of casual, but for a different reason: As a 17-year-old Canadian, he’s treading lightly on the aesthetic front, channeling the likes of Hanson or The Moffatts, who opted to dress like regular teen boys over being the next coming of fashion Christ -- mainly because they’re still trying to prove themselves musically.

Will they live to regret it? Shawn will wake up daily and give thanks to Taylor, Zac, and Isaac for paving the way for non-offensive dude style. Zayn is more like all of us: He will look back on his early twenties and shudder at his choices.

5. WIDE-BRIMMED HATS

As seen on: Justin Bieber, Harry Styles, James Bay, Liam Payne, Nick Jonas

I know we all want this to work. I know a hat seems like the easiest way to say, “I am an artist who listens to Fleetwood Mac.” But there has never been a time when a wide-brimmed cousin-of-a-fedora looks like anything but the man fronting for a turn-of-the-(18th)-century religious sect. Harry Styles, you are not a deeply religious Appalachian farmer; take that shit off.

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Will they live to regret it? Has a hat trend ever ended well?