It's hard to say when exactly I gave up on trends, I just know that it happened. It was inevitable, I suppose. No one ever thinks they'll give up on the trappings of youth—whether it be new styles of clothing or music or eating fast food or simply going out late—until they suddenly find they can't remember the last time they ate McDonalds or went to bed after midnight. And it's not just because of a faltering memory, either. Like Blink 182 once said, "I guess this is growing up."

You see them all the time if you know where to look, especially in New York City. Those people, generally middle-aged or older, who have clearly reached a certain point in their personal style and decided, well, this is as good as it's ever going to get. They're at the back table in Starbucks, on the subway, on benches in the park, dressed like they stepped out of a '70s Sears catalog. Hell, they're your parents, and they probably gave up right when they had you. They probably haven't bought a "statement piece" in their lives, yet they don't seem distraught. In fact, most of them seem almost serene in their unknowing. These are people who not only would never stand in line to buy an overpriced T-shirt, but they probably can't comprehend why anyone ever would. Maybe this isn't a tragedy. Maybe this is enlightenment. Maybe they're onto something.

Here, however, is where those poor souls went wrong: They abandoned new styles when fashion's progress was still linear, when progress was still progress. Staking one's claim in Sta-Prest trousers, short-sleeved polyester shirts and belted overcoats was a losing proposition from the start. The same goes for the style of many '80s and '90s subcultures that have since been abandoned by the masses, whether it be Ravers or Metalheads or Punks. Or even preppies, for that matter. Pleated khakis and a popped collar polo can look just as absurd as JNCOs and a Jamiroquai hat. Well, almost. But regardless, these are people who picked a lane and decided to stay in it. For nearly everyone, some point arrives where they say "enough."

I mentioned at the start of this that I wasn't exactly sure when I gave up, but that's not entirely true. I don't remember the date, or even the year, but I believe it had something to do with the triumphant return of the snapback. When I was a kid, especially when I was in high school and college, a snapback was something you bought when you couldn't afford a fitted. The New Era 5950 was the pinnacle in baseball cap achievement, and now I was supposed to intentionally purchase a lesser item, more often than not for more money? Fuck no. That was a deal breaker. This was, in some ways, the end—my end.

Why did this happen? In part because, sometime in the 2000s, the ever-forward march of fashion had seen multiple retro cycles spin off, moving increasingly faster like miniature tornadoes. And as the avant-garde got avanter and gardier (hi, Rick Owens), the same retro touchstones—flannel! jerseys! trucker hats!—hit again and again, doing more and more damage each time. At the same time, even those designers still continually trying to push forward were dragged into the vortex, and "new" designs bore similar elements of the past.

Basically, to throw in yet another metaphor, I can watch others try and ride the waves, while I lay on the beach, sipping an Arnold Palmer.

But even as the retro cycle fractured fashion in some ways, in others it refined things. Freed from the artificial constraints of "NEWER!," certain brands and designers chose to pillage the past (their own or others) for styles that were more timeless. Levi's, for instance, with their LVC line, brought back 501s and 505s from the '40s, '50s and '60s. J. Crew explored workwear with Wallace & Barnes, while sifting through third party offerings with its "In Good Company" selections. Bootmakers like Red Wing and Chippewa found renewed acclaim with their classic American-made styles. It wasn't just an American explosion, either. Japanese denim companies acquired vintage looms, turning out better jeans than Levi's ever did, and visvim painstakingly created new heirloom-level pieces using tried and true production methods. This had been happening slowly for years, but the 2000s was when it all seemed to come together and become...something.

"Trend" isn’t the word. It was almost anti-trend. This was a victory of quality over quantity, a recognition that even in a largely subjective industry there could be objective bests, and that there could be permanence in an industry based on planned obsolescence. As such, it gave people an out. Rather than trying to stay current—a task that actually gets more difficult the harder one tries—or pick a soon-to-be-outmoded style to stick with forever, there was a third option: timelessness. This wasn't a matter of, to put it in sports terms, taking an unproven rookie and hoping they'd pan out. This was signing a talented veteran in their eternal prime. It turned opting out from something that just happened to a conscious choice. And with that as a possibility, I opted the fuck out.

Here is what I'm wearing right now as I write this, from the top down: a New Era 5950 Raiders hat (backwards), a Terrible One T-shirt I bought nearly 10 years ago, a pair of worn-in LVC 1967 505s, a black leather Polo belt, J. Crew socks and boxers, and a pair of broken in Adidas Stan Smiths. I could have just as easily worn this in 1994 and could very well be wearing it, or something very much like it, in 2034. Although, for propriety's sake, I will probably turn the hat forwards as a 63 year old man. I do have some dignity left. Maybe I'll even throw an oxford over the T-shirt, but I will never tuck it in.

Is this essentially slashing through the Gordian Knot of style? Probably. On the one hand, I don't look like a refugee from an era long past and, on the other, I don't have to try and figure out the point of Hood By Air, Off-White or any number of other "hot" brands. I feel no need to replace all my jeans with joggers, my fitteds with snapbacks or try and comprehend the mysterious allure of the drop crotch. Basically, to throw in yet another metaphor, I can watch others try and ride the waves, while I lay on the beach, sipping an Arnold Palmer. Does this make me a quitter? A coward? A dropout? I guess. But it beats hauling a truckload of suddenly out-of-fashion shit to the consignment shop every six months.

As the retro cycle spins faster and faster and the cutting edge of fashion and style gets ever more out there, it'll be interesting to see what happens in the future. Will people do whatever it takes to stay on that edge, or will more and more eventually drop off? After all, read about "The Last Chambray Shirt You’ll Ever Need" often enough, and you may actually start to believe it.

Russ Bengtson is a Senior Staff Writer at Complex. You can follow him on Twitter here.