The Return of Flared Pants Was Inevitable

It's happening now—right now. Here's why, plus how to prepare.

The return of flared pants isn’t just inevitable—it’s already happening. That’s what I’m here to tell you today. I know that, for many of you out there, this is categorically bad news. A few others may feel a sense of ambivalence about the whole issue. Fewer still will be genuinely excited.

But the other thing I’m here to tell you is that the last group has it right. This isn’t a bad thing. This could even be a good thing. I realize that might sound entirely wrong to you. I get it. I remember Y2K fashion. I remember the "bootcut" jeans that clung to thighs but pooled—gigantic, far bigger than you need for a boot—over Etnies sneakers. It was way, way worse than everyone on TikTok would have you believe. But amidst the trash-heap of bedazzled pockets, terrifyingly tiny rises, and woefully ill-informed wash treatments, there was a nugget of goodness in those pants we wore all those years ago.

Remember when every single person doling out fashion advice told you that a subtle flare creates a longer line for the leg, a bit of visual trickery that flatters pretty much every body type? They were right. And it turns out, despite the circumference of those old-school hems quickly outgrowing the necessary size for footwear accommodation, today's flares really do sit much better over boots than their slim and skinny counterparts. But these are just practical, functional considerations. Truth be told, the real magic of the flare’s return to the limelight is all about emotion.


See, we’ve been living in boom times for anything-goes, let-your-freak-flag-fly trousers for a few years now. And that’s precisely because the era leading up to our current moment was lorded over by one fit: skinny. Everyone was slinking around in their cigarette pants and low-profile sneakers for so long that it stopped seeming revolutionary—which it was when Hedi Slimane proposed the silhouette during his Dior days—and started feeling…regular. We were like the proverbial frogs in a pot, except instead of slowly boiling to death, we simply allowed our calves to be ever-more strangled.

Wrancher Dress Jean


Then, the pendulum started swinging. It always does. But instead of moving in one direction, it careened in a million different ones. Cropped and tapered! Long and loose! Straight-leg for the trads and dads, drop-crotch for the fashion fans. Everything—everything—was on the table. Still is. Except, of course, for the flare.

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The flare remained—still remains, for many—the one verboten style in the grand pantheon of pants. That we all might be a bit gun shy after its last outing makes sense. But also, isn’t it kind of silly to embrace everything from wide-leg painter pants to drastically oversized wool trousers and leave this one silhouette, which in comparison actually seems pretty tame, out of the mix? I’d say it is. And it would seem the designers and brands of the world agree.

So High Bootcut Jeans


Over the last few years, the flare has been bubbling back into the mix. Fashion brands like Acne Studios and Gucci have been putting out tailored versions, as often in the context of a suit as not, for multiple seasons. You can find similar shapes at Louis Vuitton and Dior now, too. On the mass-market side of the equation, Levi’s has lately been pushing styles like the newer So High Bootcut—a distinctly ‘70s-flavored flare—to supplement old-reliables like the 527. And brands like Abercrombie (for the ex-bros) and Wrangler, with its Cowboy Cut denim and (genuinely great) Wrancher “dress jeans,” never really walked away from their bootcut offerings. Even in the context of athletic-inspired pieces like track pants, the flare is coming into play via designer labels like Casablanca and Wales Bonner. It’s happening, folks. Whether you like it or not.


Flared Ruffled Wool and Mohair-Blend Trousers

Acne Studios

So why now? Well, for one thing you can’t ignore the current influence of the ‘70s on menswear. Funky patterns, tinted shades, flowing shirts. These are all still going strong, and the flared pant fits right in with them. Maybe everyone just wishes they could be doing cocaine off a glass-and-brass coffee table in the Hollywood Hills.

But ultimately, this feels like it’s part of something larger and more organic: the natural ebb and flow of fashion. Something comes into style. It hits ubiquity. It begins to transition and twist and mutate into an exaggerated version of itself as brands and Instagrammers vie for attention in an increasingly crowded marketplace. (See, for another example, the monstrous Frankenstein sneakers born out of the dad-shoe trend.) Eventually, as with those floppy, low-rise, ultra-tight flares of yore, we tire of it.


Slim-Fit High-Rise Flared Jeans


Then enough time passes. Something else—say, the skinny jean—comes in and goes through the same life cycle. We look back and realize maybe what we ultimately rejected was a perverted version of the thing. We start to consider what a more subtle pair of flared pants might be able to do. And as early adopters, stylish as they tend to be, begin incorporating it back into their wardrobes, we realize that, Hey, that actually looks pretty great. And suddenly, you’ve got a few pairs of flares in your rotation.


La Flare Distressed Two-Tone Jeans

Gallery Dept.

Again, I realize this may not come as welcome news. Maybe I can soften the blow. Because one huge advantage of this burgeoning moment over the last time around is that there’s not one style to rule them all. You can wear your flares and your baggies and your slim-fits and your whatever-the-hell-you-want. But the fact of the matter is the flares are back in the conversation—and maybe, your wardrobe. It was, after all, inevitable.

Flared Distressed Jeans


FromEsquire US

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About The Author
Jonathan Evans
Jonathan Evans is the style director of Esquire, covering all things fashion, grooming, accessories, and, of course, sneakers. He lives in Brooklyn with his wife and son. You can follow him at @MrJonathanEvans on Twitter and Instagram.
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