How to Wear a Flannel: Easy Men’s Styling Tips

Winter is the ideal season for cozy sweaters, flavorful punch, and—of course—styling a flannel shirt. Much like the warm glow of a crackling fireplace, flannel has an inviting quality that makes it a favorite during the colder months. Perhaps it’s its soft texture or its classic plaid patterns, but the flannel shirt has earned its place among the pillars of Americana—right alongside blue jeans and white tees—thanks to its incredible versatility.

Originally crafted from woven and brushed wool to keep farmers snug in 17th-century Wales, it was the Industrial Revolution that truly democratized flannel attire and turned it into the fashion essential we all know and love. Nowadays, flannel is as in trend as ever, with roots that run deep in workwear and pop culture. Don’t believe it? Join us as we explore how to create the best flannel outfits for men together!

What is a Flannel Shirt

Flannels have earned a timeless spot in the working man’s wardrobe, on and off the job. These button-ups are made from soft-woven fabrics—usually cotton or wool—and are a staple for many. The flannel material is milled or raised with a more robust texture compared to other casual or button-up shirts. These pieces are very popular in colder regions and are often viewed as vintage-inspired pieces with roots in Western fashion.

While the checkered flannel shirt style has taken center stage in mainstream fashion, we also have great options in plain, solid colors. Although people often associate flannel shirts with checkered patterns, solid-colored options can offer a more urban, understated look. Checkered and patterned flannels, on the other hand, come in countless designs—with lines, squares, and intricate details. It’s ultimately up to you to choose which patterns resonate with your personality. A good starting point is simple checkered patterns that pair well with most of your pants, and from there, you can gradually experiment with bolder designs as you see fit.

Men's Flannel Outfits

How should you wear a flannel shirt? Luckily, its style makes it versatile enough to easily fit into numerous outfits, but having a few handy tips will ensure you nail the look every time. That's why we've gathered some reliable styles and proven strategies for incorporating this fabric into your everyday wardrobe. Let’s dive into styling a flannel shirt for guys right away.

Flannel Shirt with Denim Jacket

This flannel outfit radiates a masculine charm—perfect for transitional weather and casual outdoor adventures. At its core, the casual flannel shirt embodies a workwear aesthetic. The whole ensemble gains texture and a vintage edge thanks to a denim jacket with the baggy jeans creating a clean silhouette. Overall, this style is well-suited for weekend outings or laid-back meetups with friends.​

Pair your checkered flannel with the Washed denim overshirt and the Tapered jeans from Les Deux for a look that combines urban aesthetics with workwear touches.

As an Outer Layer

This outfit embodies a classic style that is never gonna fade away. It showcases a plaid flannel shirt, which is casually worn open over a plain white tee. Paired with black tapered pants, the outfit achieves a nice balance and structure and serves ideally for everyday activities—grabbing coffee, hanging out with friends, or simply taking a stroll around town. 

Let’s style the Flannel check overshirt from Les Deux with the Tapered classic jeans from Citizens of Humanity and the white Crewneck loose-fit t-shirt underneath. As simple as that, but the impact is enormous.

Flannel With Puffer Jacket

This laid-back streetwear outfit showcases a plaid flannel shirt layered over a sleek knit, topped off with a comfy puffer jacket. When paired with casual trousers and polished leather shoes, it brings together the urban style and comfort of essential clothing. This ensemble is ideal for your daily routine on chilly and rainy days.

Make your flannel shirt the middle part of your sandwich with the Puffer jacket from Moose Knuckles on top and the Rollneck cashmere pullover from FTC Cashmere underneath.

Smart Casual

This smart casual look blends rugged and refined styles into one well-balanced picture. A plaid shirt adds texture beneath a tailored blazer paired with matching trousers for a polished vibe. Yes, flannel works as a part of business casual attire for casual Fridays or creative work settings.

You may style a plaid or solid-colored shirt here, yet we suggest going with a single color in a neutral shade. As for the tailoring, check out the brown suit from Tiger of Sweden featuring the Slim-fit blazer and the Straight-fit trousers. Be careful with the hues, and don’t get too edgy with the accessories.

As a Middle Layer

What is a flannel shirt if not the ideal layering piece? We’ve already talked about how it works as a light overshirt, but this also makes it suitable for wrapping up when the mercury drops. The right street-style flannel brings additional depth and texture with layered looks. Wear one over a T-shirt and then throw a lightweight jacket or a vest on top for ultimate cold-weather protection.

​We’ll pair the Check flannel shirt from Les Deux under the Lightweight neoprene bomber jacket from Blauer with the basic long-sleeved tee and a pair of trustworthy matching trousers.

Flannel under Cardigan

A great jacket substitute would be a cardigan—easy to slip over your flannel shirt—buttoned with a pleasing V-shape that will allow your shirt collar to pop. Sweaters are another great option for pairing with preppy flannel shirts. While there are many different styles available, it’s generally best to avoid crewnecks. Much like a cardigan or sports jacket, the V-shape won’t constrict your shirt’s collar, meaning you simply need to pull on your sweater and go about your day without having to readjust your outfit. Due to the casual nature of flannel shirts, you’ll be better served by avoiding flat, plain knits. These are great for dressier outfits, but a flannel shirt requires something a little more relaxed. Look for interesting weaves, such as chunky or cable knits.

For our outfit, we mixed the Flannel check overshirt from Les Deux with the Casual chino-fit trousers and the Chunky knit cardigan from Tiger of Sweden. A little bit preppy, a little bit utilitarian—ideal for daily errands.

FAQ

How should a flannel fit

Aim for a fit similar to a dress shirt: it should be neither too long nor too short. Your flannel shirt should offer a comfortable fit—not too snug, yet not overly loose—allowing you to strike that elegant look while wearing it.

Is a flannel business casual

Flannel can work for a business casual look—just keep things simple. Choose a solid color or a nuanced pattern, tuck it into chinos or slacks, and layer it with a sweater or blazer. Keep the sleeves buttoned and pair it with loafers or oxfords to ensure your outfit is office-ready. 

How to dress up a flannel shirt

Flannel shirts can be easily dressed up for semi-formal dress codes. Opt for a well-fitted flannel in neutral shades like navy, gray, or deep green. Pair it with dress trousers or chinos, and layer it with a blazer. Avoid overly bold patterns; instead, choose subtle plaids or solid flannels that enhance your outfit without drawing too much attention.

What shoes to wear with a flannel shirt

Consider styles like Derbies or loafers, especially in suede. Want to add some extra texture? Various types of boots can work beautifully as well—Chukka and Chelsea, in particular, create a stylishly casual look.

Flannel vs dress shirt

Flannel and dress shirts serve different purposes. Flannel is softer and warmer, making it ideal for casual outfits and layering in cooler weather, while a dress shirt is lighter, smoother, and designed for more formal looks. Each brings its own strength—comfort and texture on one side, structure and polish on the other.

Flannel tucked or untucked

The untucked flannel has often been linked to skaters, hipsters, and other ultra-casual subcultures. By tucking your flannel into your pants, you stand out and also add a touch of polished flair to your look.