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Right around the turn of the last decade, something strange was happening. Guys—young guys, cool guys—started dressing like their grandfathers. Voluntarily. Most fashion trends feel emergent, something unpredictable that bubbles up from the soup of culture and life. This one was much simpler than that: It was beamed in. Or, more precisely, it was carried in by the apparatus of what would soon be known as “premium” cable. The Mad Men look—skinny ties, gray suits, perfectly creased pocket squares—was inescapable.

Jon Hamm, aka Don Draper himself, at the Mad Men Season 4 premiere in 2010. Note the skinnier tie, plus the subtle contrast-collar on the pale pink shirt. Getty

Granted, Mad Men started airing in 2007, and within a year became a cultural phenomenon (if not a ratings success). But menswear tends to move a little slower than culture at large, and it wasn’t until the beginning of this decade that it took hold in real life. By the early 2010s, the J.Crew Ludlow suit, launched a year after Mad Men in 2008, was ascendant (and never without a pocket square in the breast pocket). In 2011, the show’s costume designer, Janie Bryant, teamed up with Banana Republic on a capsule collection inspired by the men of Sterling Cooper.

In the early 2010s, guys were suiting up, shining their shoes—and learning a whole new set of rules about how to dress. At the time, it felt kind of great. The prior decade, from its Von Dutch trucker hat down to the hems of its bootcut jeans, wasn’t exactly a high-water mark for men’s style. And after the financial rug was pulled out from under a generation of young professionals in 2008, looking to the past felt safe. Smart. A guaranteed path to good, lasting style.

Call it the evolution of the "suit." Bradley Cooper’s mid-gray windowpane check (2012) vs. early adopter Jaden Smith’s graphic pair-up (2016). Getty

Now, a decade later, that mentality seems almost quaint. Style stars like Timothée Chalamet, Chadwick Boseman, and Harry Styles are wearing the kind of stuff that would have been inconceivably weird in 2010. And on the eve of 2020, real guys are following suit (and, to be clear, it’s with actual suits that this is most evident). If the 2010s was the decade in which men grappled—publicly, painfully—with how to be a man in the modern world, it was also the decade in which we—generally more privately, except for celebrities—began to ask ourselves how to get dressed in this new landscape.

For all the talk of athleisure and streetwear and everything else, when it comes to fashion, the 2010s will be remembered as the decade in which we stopped obsessing over how a man “should” dress and finally started having a little fun.

Colin Hanks went as classic as they come with a dark suit, skinny striped tie, and a tie bar in late 2012. Harry Styles? He went for something (very) different in a sheer shirt and flowy trousers at the 2019 Met Gala. Getty

There are a couple of crucial things to remember about the Mad Men style moment, especially when it reached fever pitch. The first is that it was fueled, in no small part, by the internet. Just Google “how to dress like Don Draper,” and you’ll find a cornucopia of established sites and fledgling menswear blogs alike, all eager to tell you what to do. The result: a feedback loop. Guys were searching for answers to a straightforward question, and because the universe hates a vacuum, the internet stepped in to fill the void.

The problem is that these answers, as they tend to do, took the form of mandates. “You should have a pocket square, or else you are not a well-dressed man.” “Your tie should match the width of your lapel, lest you look unkempt.” Not all of these ideas are bad—in fact, the one about ties and lapels is good to keep in mind to this day—but for those guys searching for guidance, they created a sense that there’s a universal set of rules. For getting dressed, sure, but also for being a man.

Ryan Reynolds still has a bit of a trad streak today, but this super-skinny tie (plus tie bar, of course) in 2011 had "Mad Men style" written all over them. Getty

It doesn’t help that the fashion being emulated, in this case, was from the early ‘60s (which, as Vanessa Friedman pointed out at the New York Times when Mad Men was ending its run, looks a lot like the ‘50s). There’s always the danger, when fixating on an era’s dress, of conflating it with all the other stuff associated with that era. Put another way: If you’re dressing like a man dressed in 1960, are you channeling only his fashion sense, or are you maybe thinking about a three-martini lunch, and how you might look cool with a cigarette, and (here’s where things get dangerous) returning home to a life and family that look a lot like they might have in 1960? Are you wearing a suit, or a half-century-old conception of how a man should live his life?

The guys who were straightening their tie bars in the bedroom mirror in 2010 (or 2012, or even 2015) weren’t getting ready to head to the smoke-filled offices of Sterling Cooper. But they were searching for the rules that defined that dress code. They were internalizing dictums about fit and fabric and pattern and color from a time when what a man could be seemed less important than what a man should be.

David Beckham is goes a little less bold than some of his contemporaries, but this perfectly complementary look with wife Victoria Beckham in 2018 is good evidence that he’s learned how to toy with traditional masculinity a bit. Getty

Here’s the other thing about the Mad Men style moment: It passed. Most notable in its wake: the rise of both athleisure and streetwear, two style movements that are almost aggressively unconcerned with what a man should wear (and where). Sweatpants—expensive ones!—for everything? Absolutely. A graphic tee that, only a few years earlier, would have been dismissed as unforgivably juvenile by the man in the zero-break trousers? Sure, and throw some high-fashion basketball shorts in the mix, too. And then let’s wear them to dinner. Oh, and let us not forget the ultimate anti-Mad Men look: sleaze.

But while athleisure and streetwear and dressing like a teenage weed dealer feel, especially in retrospect, like a reaction to the impressively long reign of Mad Men style, something much more interesting is happening right now, as we teeter on the brink of the ‘20s: Guys are going wild, and they’re doing it in a decidedly non-casual way. Look to someone like Harry Styles, a de facto standard-bearer for this new menswear moment. His (ahem) style couldn’t be further from the empty-suit uniformity of Don Draper. But he’s upending our collective idea of how the modern man might dress while wearing suits, and high-waisted trousers, and sweater vests—the stuff of ‘60s closets, just taken to a whole other plane of existence.

Chadwick Boseman at the 2019 Academy Awards: all flowing fabrics and glittering accents. Getty

Or consider Chadwick Boseman, with his floral brocade jackets and flowing silks. Or Timothée Chalamet, wearing a screaming pink suit from Stella McCartney—and the women’s collection, no less. (Oh, and that was after Jaden Smith modeled for Louis Vuitton’s womenswear collection way back in 2016.) These guys are playing with the very core of the expression of masculinity. And while they’re doing it on the red carpet, early non-famous adopters do it in SoHo and Echo Park and on Instagram. And it feels fun! And new! And daring, and maybe even a little dangerous.

Nothing says "mid-century style" quite like Don Cheadle’s hat paired with that gray suit at the 2010 premiere of Iron Man 2. Timothée Chalamet’s exploded floral suit, from 2018, says something quite different. Getty

But most of all, it feels refreshing. Because while it is abundantly clear that these get-ups are extremely considered—just try to fool yourself into believing Harry doesn’t know exactly what he’s doing when he puts on his latest out-there outfit—they also feel unconstrained. You don’t land on these clothes by considering how a man should dress (unless of course that man is David Bowie). You land on them via experimentation and risk-taking and considering how a man could dress now, in 2019, on the cusp of a new decade.

A suit will never go out of style. A perfectly put-together outfit, informed by the classics, is rarely a bad idea. But there’s so much more to men’s style than that. And over the last 10 years, we’ve finally come to understand that we’ll never break new ground if we keep playing by the same old rules.