Tips for Dressing Up a Flannel Shirt

Fall and winter are the seasons for pulling out that old friend, the flannel shirt. The material is largely popular for its warmth and soft texture. It’s also incredibly versatile and easy to wear virtually anywhere, from weekend football games to Sunday brunches to holiday shopping excursions.

Despite that level of flexibility, it’s also true that flannel tops are incredibly casual. That means you may relegate them to off-duty events instead of considering them for anything even remotely dressy. That’s understandable. Most people wouldn’t look at a flannel shirt and accuse it of being fancy. But in the world of fashion, virtually anything is possible with a little bit of creativity and ingenuity. When you play around with the possibilities, you’ll quickly discover that flannel is surprisingly easy to dress up—just as easy as it is to wear it more casually. Here’s everything you need to know to give it that dressier spin.

Begin with High-Quality Flannel

How do you find the best flannel shirts? Look for ringspun combed cotton – and look for something that's brushed on both sides, not just the outside. That's how we make our Flagship Flannel™ here at Lands' End. That goes for everything from our classic button-front tops to our flannel tunics.

We comb the cotton to remove shorter, weaker fibers, which will help the fabric resist fraying and pilling down the road. Then we use the ring-spinning technique, which creates smoother yarns that can be woven tighter, making the fabric stronger. Lastly, we brush both sides of the fabric, so it's not just soft outside – it's cozy inside, too. Who wouldn’t want to go casual in something that feels so good?

Dress Up Casual Flannel Outfits

There are few garments as comfortable as flannel shirts. They just look cozy—and are so soft you might want to wear them to bed! But because they pretty much define casual perfection, that also makes them fantastic candidates for your laid-back weekends. Pair yours with your favorite classic jeans and step into a pair of sneakers or basic boots. More than just a weekender outfit, it’s also an option to wear to a casual office.

Want to dress up your shirt a little bit, even while going relatively casual? Guys can pair theirs with some crisp men’s chinos with a more slim fit to create a balanced look from top to bottom. Women will love their breezy flannel top with sleek leggings. Add a pair of rugged boots or suede booties to complete the look.

Make Flannel Dressy with Accessories

Don’t believe that a casual top can ever look dressy? Think again. It’s all in what you pair it with—and how adventurous you choose to be. Even the most low-key pieces can look dressed up if you add one or two unexpected elements to the mix. Take an approach inspired by the 1970's and tuck your flannel shirt into a pair of classic corduroy pants. Opt for one with a wide leg to create some visual balance. This silhouette is also friendlier to heels and boots, so you can easily add some polished footwear to the mix to really bring your outfit into dressier territory. A strappy stack heel or a pair of chunky booties will work well.

You can even take flannel in a pretty direction with the right accessories. Begin with your shirt of choice. Since it’s the sole pattern in this outfit, make it count by selecting a color palette you absolutely love. Then pull on a pair of sleek dress pants, ideally one with a straight or fitted silhouette. Tuck in the shirt, and add a belt in a color that contrasts well with the shirt, like a rich black or mahogany leather. Look for a belt that has a decorative but not too ostentatious buckle for added dressiness. Finish with a necklace in a metal that matches the buckle. You can pair this outfit with heels for a truly dressed-up ensemble you’ll love to wear.

Layer It Over a Dress

You may be surprised to find just how well flannel shirts pair with dresses for women. Use your flannel top to make maxi dresses a more integral part of your fall wardrobe. While you may typically retire them at the end of summer, maxis become far more wearable when you toss a flannel shirt on top and knot it at the waist. Add a few layered necklaces and slip into a pair of metallic sandals to complete the look.

You can try the same with virtually any other type of dress, whether it’s a midi length, a fit-and-flare style, or a shirt dress. Add a pair of tights if it’s cold outside, or try a pair of leggings if you need even more warmth. With a shorter dress, they’ll be perfect for providing the coverage you need. Play up the shirt’s versatility by belting it at the waist with a sleek or thick metallic belt, or by looping a chain belt around the waist for interesting contrast.

Where to Wear Dressy Flannel

It’s not just easy to dress up flannel—it’s also easy to wear it in so many different environments. Of course, it’s the go-to choice throughout fall. You’ll find yourself reaching for it when you take the kids to the pumpkin patch or when you go watch your team score big at the football game on Sunday.

But being that you can dress it up, it’s not just suitable for casual spaces. You could even conceivably wear your flannel on date night, especially when thrown on over a dress. Why not try it with sleek black leggings or skinny jeans and a structured blazer. Wear the shirt slightly undone, with layered necklaces to create an interesting focal point. Finish with pointy-toe boots or strappy sandals.