Guys, Flared Jeans Are Back—Here’s How to Rock Them Your Way

The fashion world has a funny way of circling back when you least expect it. Things you swore off in high school—frosted tips, ironic trucker hats, overly long wallet chains—might not be getting a revival just yet (thankfully), but pants? Pants are making moves. More specifically, there’s a shape coming back from the shadows of ‘70s photos and early 2000s rebellion, and no, it’s not skinny. Guys are finally loosening up again. Literally.

Why Flares Work Now When They Didn’t Before

Let’s get one thing straight: men didn’t suddenly grow fond of more fabric. What’s changed is how people wear it. The old idea of flares came with a lot of baggage—cheesy rock bands, bad bootcut fits, stiff denim that looked better on mannequins than actual people. But now? There’s a cleaner, cooler way to do it, without trying to look like you just time-traveled from 1974.

The key is how the jeans fall—not how wide they get. A good pair will break just right over your shoes, without bunching or ballooning like you’re walking around with parachutes strapped to your calves. Flared jeans pull focus without screaming for it. You don’t need platform boots or fringe jackets. Just the right vibe. Confidence helps too, but you don’t have to have it figured out on day one.

Balancing the Top Half

This isn’t math class, but proportions matter. When your pants start to widen, your top half needs to tighten up a little—or at least know when to chill. That doesn’t mean squeezing into something uncomfortably snug. It means being intentional. A fitted tee, a tucked-in button-down, a clean hoodie that stops at your waist instead of hanging past your pockets—all solid moves.

You want your silhouette to feel like it has structure. Wearing flares with an oversized hoodie that swallows your torso is like trying to see a picture that’s zoomed all the way out and all the way in at the same time. It just looks…confused. Flares ask for a little more thought up top, but once you nail that shape, it opens up all kinds of possibilities. Guys who used to live in joggers are now reaching for things with collars and zippers again, because the pants are pushing them in that direction.

The Shoe Game Just Got Interesting Again

You can’t just throw on any old sneakers with flares and hope for the best. Shoes matter more when your pants are calling attention to your feet. Low-tops might get eaten by the fabric, high-tops need to make sense with the overall outfit, and loafers? Surprisingly solid if you’re feeling grown-up.

The sweet spot tends to be something that holds its own. Not clownishly large, but not delicate either. You want to see the shoe peeking out, not just a limp hem swallowing it whole. Boots, chunky sneakers, even some of the newer hybrid slip-ons guys are messing with—they all work if they’ve got some heft.

The best thing? You’ve got room to experiment again. And let’s be honest, after a decade of looking like we were all shrink-wrapped into our pants, it’s kind of a relief to let your ankles breathe.

Choosing the Right Pair Without Screwing It Up

There’s a lot of garbage out there right now. Too many options trying too hard to be edgy or vintage or whatever buzzword they’re tossing around this month. What you need is a pair that feels like you—not your dad, not your younger cousin who goes viral on TikTok for thrift flips, you. That means checking the rise (no one wants low-rise back, not even as a joke), looking at the length, and making sure the flare actually starts below the knee—not creeping up your thigh like it’s confused about being a bellbottom.

If you’re not sure where to start, skim some racks in person and try stuff on. Better yet, take a friend who’ll tell you if you’re being delusional. The internet has a jeans buying guide for everything, but most of them are written like you’ve already done three semesters of Fashion 101. Trust your gut. If you look in the mirror and feel like a cartoon version of yourself, try a different cut. But if you find a pair that makes you stand straighter and walk with that slight click of “I’ve got this,” then congrats—you’re in.

You Don’t Have to Go Full Rockstar

There’s a version of flares that lives in your head as a joke. It’s the velvet jacket, chain-smoking frontman, way-too-deep V-neck shirt version. Forget that guy. You don’t need to become him to pull off flares. You can be the dude at the coffee shop who looks just a little more put together. The guy who always seems like he knows where he’s going—even if he’s just headed to the grocery store.

Start small if you want. A darker wash. A subtle flare. Keep the rest of the outfit simple and let the pants do their thing. Or go louder if that’s your speed. Mix textures, mess with layers, try on a jacket you usually wouldn’t wear. Flares aren’t just pants—they’re an excuse to rethink your whole outfit in a way that doesn’t feel like work.

At the end of the day, style should be fun. Not stressful. Not stiff. Not dictated by what’s trending on some app that stopped being cool five months ago. It’s about finding a way to feel like yourself—just maybe a slightly upgraded version.

Wrapping It Up

You don’t have to change who you are to wear flares. But you do have to commit. Pick the right pair, figure out your top half, and let your shoes step up a little. That’s it. The pants will do the rest.