90s Flannel Is Back. Here’s How To Wear It Like A Supermodel

There are some fashion items that never go out of style: a silk blouse, a good pump, the little black dress. These are evergreen pieces that you’ll wear in perpetuity and are quite literally investments in your future. Personal style is serious business.

There are other items, however, that we may not necessarily have deemed “fashion,” historically, but are household names nonetheless. These pieces are just as useful. However, unlike the evergreens, they tend to come and go, popping in and out of our lives as utility demands.

And then there are pieces that have, over time, proven themselves so invaluable to us that they switch from one category to the other, seemingly all at once. What was once a “here today, gone tomorrow” throwaway is now a ride or die staple. Which brings us to the current moment. One such shapeshifting item is rising in the style ranks as we speak. Yes, we’re talking about the holy grail of homesteading attire, the casual 90’s throwback, the obvious must-have for fall and winter. Flannel has reentered the chat, and it’s causing a real ruckus.

Giving instant nostalgia for freshly chopped wood, a cozy cabin, and a strapping lumberjack, it may seem obvious that flannel would always have a place in our fashion repertoire. But it has certainly fallen out of favor from time to time. Sometimes associated with a function over style approach or subversive 90’s grunge, it hasn’t always been the choice of the trend-savvy. For better or for worse, it has, in the past, occasionally been relegated to the fringe.

No matter how deeply we kept it buried within our Le Pliage tote, flannel’s obvious irresistibility was bound to resurface eventually.

But no matter how deeply we kept it buried within our Le Pliage tote, flannel’s obvious irresistibility was bound to resurface eventually. Et voilà, here we are. In 2025, girls are once again embracing the cozy and homey top, and the outfits are snapping. Oversized flannel paired with baggy jeans, a basic tee, and some really good hair and you’ve got a beautiful new rendition of big city meets small town. Seventh Ave meets country road. A folk fashion triumph. Just ask the locals. They always know.

But how do you style it without looking like Uncle Phil (whom we love)? Understanding its essence is essential. Aligning perfectly with the oversized moment we remain in stylistically, flannel isn’t so much about snatching the silhouette as it is about leaving something to the imagination. The point is effortlessness, girl next door. It gives borrowed this from my boyfriend and he’s not getting it back. It’s as gone as last month’s paycheck.

Making it feminine is the key to avoiding frumpiness. There are a myriad of ways, as long as you’re intentional. Do it well and you’ll have a look worth replicating. Worn just as easily to a weekend football game as to brunch with the girls, one thing’s for certain: flannel is doing the work right now and keeping it down home.

Here’s how the fashion-forward have styled it as of late:

Oversize it

As we all know, girl closets right now are 90% oversized and 10% teeny tiny (like could fit an actual baby). Flannel works best in the former category. The hottest tops for winter look like they’re about to fall off your frame at any given moment, and flannel is no exception. Drowning in it is the vibe, the bigger the better. As usual, cute hair and lip gloss keep it girly. When you’ve nailed the basics, it’s really hard to mess this one up. Oversize fits all.

Open

Open and free seems to be one of the more popular iterations of the flannel retelling this time around. Oversized flannel worn unbuttoned and unburdened reads cool girl chic and doesn’t care what others think. Paired with a fitted tank or basic tee and baggy jeans ensures both fitting in and standing out, which is what it girls do with ease. The motto: keep it loose and win.

Closed

Alternatively, worn all buttoned up and tucked into your favorite pair of jeans presents a more polished version of the flannel offering. This is perfect for any less casual activity. A belt and a bob complete the look. Or go waist accessory free for a more relaxed but still sensible variation of the trend. Chic boots or loafers are a bonus. When you’re hot and young, you make the rules. All of them.

All tied up

There’s nothing more 90’s than a tied up top. A knotted flannel takes the throwback cake. And brings the outdoorsy boys to the yard. Pair it with a ballcap and leather tote and you’ve got yourself a genuine cowboy fly trap. Sporty, without having to get your hands dirty. The results? Damsel-status preserved, fresh manicure and farm boy approved. Which is all any of us ever wanted.

Layered

Every good fashion girl knows that layering is the key to iconic style. Upgrade your flannel by pairing it with a sturdy barn jacket for New England charm. Or layer a cozy cashmere sweater for a more elevated look. Drape the sweater over your shoulders or tie it around your waist and you’ll be manifesting first-class abundance in no time. Dress for the seat assignment you want, experts say.

As an accessory

This time, the flannel is almost an afterthought, but not really. Paired with a simple sweater and leather jacket, a flannel around the waist somehow gives you a mysterious quality that will undoubtedly intrigue. Not quite grunge, but edgier than everyday, the soft plaid accessory will have them wondering if you’ve just authored a moody novel or been lead singer in a band. As we know, it’s important to always keep them guessing. Maintain the je ne sais quoi.

Under a vest

Vests are hot when it’s cold. Over a flannel? Stratospheric. Yes, pairing flannel with a sleeveless coat inexplicably takes your outfit from JV to Varsity in nothing flat. One of life’s great mysteries. Go neutral to blend in with the falling leaves or make it pop with some complementary seasonal color. There are no wrong answers here. We don’t pretend to understand it, but the flannel and vest combo is an outfit MVP, guaranteed.

Matching with your man

The ultimate act of love: matching with your main flame. His and hers flannel is about as intimate as you can get. Actually. And if you can get him to do it in public, he’ll be yours forever. The revenge pics would be too damning if he ever left. A little sartorial blackmail never hurt anyone.

Conclusion

This winter has a new boss and it’s covered in plaid. So whether you’re looking to attract a burly mate, make a throwback statement, or simply stay cozy this season, flannel is a surefire staple for the siren rotation. Wear it oversized and open for effortless chic or tie it up with the right accessories for hometown honey and you’ve got yourself a checkmark-verified look. Charming and chic. Cozy and cool. Winter fashion equals case closed.