How To Wear A Flannel Shirt: 18 Rugged Looks For 2024

The flannel shirt is a casualwear staple and for good reason. With its roots in American workwear and longstanding associations with lumberjacks, grunge and 90s skate kids, the appeal of the flannel shirt is wide and varied. It’s ideal for wearing with indigo denim and leather boots, but looks equally cool worn open over chinos and sneakers. With a heavier weight than regular shirts it can also double up as a makeshift jacket, while it rivals an Oxford shirt with its layering abilities.

In short, if you don’t already have one, you need a flannel shirt. From choosing fabrics to settling on the right pattern, here’s everything you need to know about this iconic piece of Americana.

How to wear a flannel shirt

Fabric choice

Traditionally, flannel was always made from wool. Head into your nearest vintage shop and chances are you’ll find row after row of flannel shirts. Pick one up and it’ll likely feel rough and coarse to the touch due to the rugged nature of old-school worsted wool flannel.

This is the reason why the majority of flannel shirts today are made from cotton. Much softer and less scratchy, modern flannel fabrics still give the look of wool flannel, but won’t sand your skin off in the process.

Flannel is typically ‘napped’, meaning it’s been brushed for an extra soft hand feel. So if you’re after an authentic flannel shirt, the likes of which your great grandfather would have worn to fix his car, go vintage and scour the racks of your local thrift store. But if you want comfort and warmth, seek out a contemporary cotton flannel shirt and reap the benefits.

Embrace some colour

If you want to start wearing more colour, flannel shirts are a great place to start. Brushed cotton flannel takes colour especially well, so it’s just a case of deciding on a palette you’re after and taking it from there.

You can find flannel shirts in practically every colour and pattern imaginable, from classic green and blue Black Watch tartan through to sleek monochrome houndstooth patterns. But they also come in more out-there shades, from red, white and yellow multichecks through to grungey black and red plaid.

If you’re new to wearing colour or want to subtly brighten up your looks, try going tonal neutrals. A flannel shirt in blue or bottle green will be surprisingly versatile and will pair well with other casualwear staples including raw denim jeans, chinos and T-shirts.

Don’t neglect the details

Similar to the fabric offering, flannel shirts come available in a wealth of differing designs. The shirt’s heritage as a workwear garment means you’ll often find them with functional details including chest or even side pockets, which give them a more jacket-like feel. Designs like this take on a more utilitarian feel, making them ideal for wearing with other blue collar pieces such as carpenter pants, leather boots and chore jackets.

For something slightly smarter, opt for a slimmer design without pockets. Go for a shirt with a button-down collar and a classic curved hem and you’ll find them slightly easier to dress up, perhaps tucked into tailored trousers with Derby shoes. It’s worth noting though that the flannel shirt is an inherently casual piece, so avoid wearing them with formal tailoring.

Flannel shirt outfits for men

90s-inspired flannel

Flannel shirts have plenty of history with the 90s, particularly in the grunge scene where they were favoured by icons like Kurt Cobain. To try channelling the aesthetic today, avoid the unwashed hair and slim down the fits slightly, with a pair of regular cut stonewash jeans and canvas slip-ons.

Texture Mixing

One of the most appealing aspects of choosing a flannel shirt over, say, a standard cotton version or Oxford button-down, is the amount of texture it brings to the table.

Its tactile nature and the weight of the cloth allows you to introduce other heavier, complementary fabrics elsewhere – as shown here in the form of a pair of cord trousers. The soft, raised nap of the flannel, combined with the rows of velvety cord, gives this outfit an extra dimension, creating visual interest from top to bottom.

Anchor it all with black canvas high-tops and a plain tee.

Flannel shirt & suit

Where a flannel shirt can work with tailoring is with an unstructured suit. Providing the shirt is made from a thinner fabric, it can add a pop under a softly-cut blazer without ruining its line by being too bulky.

When choosing a shirt, try picking out a colour in the pattern that complements the suit, which will ensure the two work in harmony.

Lumberjack-style flannel

The flannel shirt will always be associated with the lumberjack, there’s no getting away from it. This is still a look that can work – just avoid the cliches, namely a large beard and endless sleeve tattoos.

A green-based flannel shirt combined with khaki pants and work boots is a classic combo that always looks great.

Monochrome flannel

While colourful flannel shirts bring interest to any fit, don’t sleep on monochrome versions. In an otherwise dark, grey outfit, this flannel shirt adds a bit of visual interest without breaking from the muted palette.

Try it as a mid-layer so that only a fraction of its pattern is showing, or wear it proudly on its own to allow the check to shine.

Flannel over knitwear

Due to its hardy and slightly heavier weight fabric, the flannel shirt can work well as an overshirt. Opt for one in place of a lightweight jacket and throw it on over a crew neck, finishing with pleated trousers and minimal sneakers.

This is a simple look but one that will see you through a wide variety of social settings, from a casual office to weekends in the pub.

Pick out a colour

One way to ensure you nail your flannel shirt fit is to pick out colours in the check with the other garments you’re wearing. Try, for example, matching your sneakers to a colour in the check, such as this muted red pair. This will give your outfit some consistency, where the shirt might otherwise have looked a little bold.

Streetwear flannel

Despite its workwear connotations, flannel shirts can work as part of a streetwear-inspired look. Try wearing one over a hoodie – just ensure the cut is boxy enough to accommodate the hoodie underneath.

Complete the look with wide-legged trousers and sneakers and you’ve got a nice balance of high/low dressing.

As a mid-layer

The layering potential of the flannel shirt is where it really shines. It can finish a look off as an outer layer, or combine well with heavier pieces as a mid-layer, providing that pop of colour that would otherwise be missing.

Whether you tuck it in or leave it untucked depends on how formal you want to look – the former always looking smarter.

Subtle colour

Flannel shirts can be found in a myriad of bold colours, but they often look their best when things are slightly more muted. Aim for one in a faded pastel check and pair it with neutral basics such as a grey crew neck and charcoal tailored trousers, and you can’t go wrong.

The flannel overshirt

Chances are you’re after a checked flannel shirt, but should you be more of a minimalist fan, they do come available in solid colours too. These tend to be smarter than those with patterns, so wear them accordingly with tailored trousers, a crew neck sweater and suede shoes for a look that perfectly borders the smart casual divide.

Tonal flannel

One of the easiest ways to wear flannel is by adopting one as part of a tonal look. Start with a base colour – say, navy – and then layer up or down as you see fit.

Try a navy flannel shirt worn under a lightweight jacket and finish with navy trousers and brown leather boots. Simple.

Flannel with lightweight outerwear

Flannel shirts are ideal for transitional seasons. For example, at the start of spring, when sudden downpours are a daily possibility, try wearing one under a lightweight waterproof mac and you’ll have a versatile look perfect for weekend wear.

Flannel shirt over a tee

Channelling more of a workwear feel, try wearing a boxy flannel shirt worn open over a tucked in T-shirt. It allows the shirt to work as makeshift jacket, making it ideal for cool spring evenings.

This outfit works especially well if the shirt features chest pockets as it’ll boast a more rugged feel suited to outerwear.

Double shirt

While a little unorthodox, doubling up on your shirts can make for an interesting and versatile layered look. Treat the flannel shirt as a jacket and wear it above an Oxford shirt and chinos for an outfit that is equal parts smart and rugged.

When indoors simply take off the top layer and you’ve got staple business casual attire.

Skate-inspired flannel

As well as its workwear roots, flannel shirts enjoyed a bit of a renaissance in the skate community in the 90s, which has lasted to this day. Try referencing a classic skate look for yourself by combining an open flannel shirt with light wash jeans and canvas sneakers.

Play with proportion

Check flannel shirts come in all shapes and sizes, from micro check and houndstooth through to large exploded checks. Go for the latter and combine it with classic outdoor staples including a padded gilet, parka, denim jeans and canvas high-tops.

If in doubt, try Black Watch tartan

If you’re slightly wary of colour, or don’t usually wear much in the way of pattern, Black Watch tartan may be for you. Made up of blue, green and black checks, it’s easy to wear and goes well with other wardrobe icons including black jeans and minimal sneakers.