Flannel Over Hoodie: How To Wear It The Right Way

Cooler winds have begun to blow, bringing with them the sounds of school bells, the sights of beautifully-colored leaves swirling around, and the smell of pumpkin spice everything. That’s right: it’s fall! After the hot summer, it’s time to turn away from the swimwear and tank tops and plan for chilly weather.

You have your oh-so-trendy knitwear, you’ve tossed away your skinny jeans in favor of relaxed-fit slacks, and you’ve doubled up on your denim. Are you really ready yet, though?

No, not unless you’ve factored in a critical seasonal piece: flannel! Flannel as a standalone, flannel over sweatshirts and tees, or flannel as the ubiquitous plaid, you aren’t ready for fall without this timeless-and-yet-timely classic!

What Is A Flannel Shirt?

Flannel has been with us for centuries. Originating in Wales in the 16th century, this fabric spread throughout Europe slowly, over a hundred years, and then to the rest of the world. Its sturdiness combined with softness made it ideal for many applications–warm, reliable work clothing, cozy bed sheets for the winter months, and the infamous red flannel union suits of the Victorian era.

Since the 1900s, though, it has become a versatile fashion staple. Among women, it was a fabric associated with designer skirts, while for men, it became a popular choice for both heavy work coats and sports uniforms. Once Gen-X took the reins of fashion, however, it was the flannel shirt that became the iconic flannel garment

A student in a flannel shirt while working on his laptop.

Embodying the ideal of fashion that transcends class, flannel shirts, whether in their common plaid patterns or a plain, soft design, are sturdy and affordable, while also able to turn heads with an eye-catching look.

Almost always, the flannel shirt of today is a collared, button-down, long-sleeved garment meant to be used in a layered outfit. Despite the buttons, it is often worn open, ready to slip on and off as needed giving you an opportunity to really show off your style by combining your flannel with a tee that expresses your personality.

Plain or Checkered Flannel

A plain flannel shirt may not at first seem to be a flannel; the plaid, checkered flannel shirt design has become so ingrained in the world of clothing and fashion that it can be hard to remember that not all flannel must have a design.

As a plain fabric in a solid color, flannel is soft, mid- to-heavyweight material suitable for a casual gathering as a standalone shirt or as a calming contrast to a tee or sweatshirt worn underneath.

Depending on the weight, it can be used as either a shirt or a jacket, and for these chilly fall days, they are the perfect middle ground between your summer and winter wardrobes. Wear your plain flannel shirt much as you would a polo, with a button or two at the top undone to show that you’re structured, but also relaxed.

The most common image called to mind by the words “flannel shirt” however, is certainly that of the checkered plaid. Originating in Scotland, the crisscrossed, colorful square patterns that were a sign of identity and power for different families were used to make kilts and shawls.

Those of Scottish lineage will be quick to point out that these patterns were not in themselves plaids, but tartans. The plaid is a long, scarf-like garment made using the tartan pattern.

Outside of Scotland, however, the term plaid has come to mean the full package: the flannel material, the tartan design, and the casual, button-down shirt that is made from them. A person might talk about a flannel coat or a plaid skirt, but when one just says “plaid”, we know they’re talking about the shirt!

Not all patterned flannel shirts are plaid, of course. There are other types of checkered patterns, some very common in flannels. The Buffalo Check is an intersection of red, black, and gray lines, and remains the most popular red flannel for shirts.

By contrast, the Gingham Check is also the intersection of lines to make square patterns, but the contrasting color is white, not black. Hound’s Tooth is another common form of the check used in flannel shirt designs; in this, instead of smooth-edged squares and lines, the squares and lines look broken and chipped.

Traditionally, this checker pattern has been primarily used in suiting materials, but as the flannel shirt widens its overlap between formal and informal, it has taken on more Hound’s Tooth patterns in recent years.

Because of the endless variety of color options with flannel shirts, particularly with plaids, you won’t want to stop with one. While establishing your fall wardrobe, experiment with several different flannel plaids and see how you can best complement the rest of your wardrobe with this one comfortable, colorful piece.

Ways to Wear a Flannel Shirt

Flannel is like a visual sponge; although it has a look of its own, it absorbs factors from the rest of your look. It can be formal, it can be casual. It can be tidy or sloppy, cheerful or subdued, conservative or edgy–and that’s all with a single flannel shirt!

Handsome stylish man in flannel shirt.

Imagine, if you will, a man in his mid-20s. He is clean-shaven, his hair is smooth and shiny, his smile confident. He stands at a corner, waiting for his car, with a straight posture and a briefcase in his hand.

Draped over his arm is a freshly-ironed blazed, the same spotless black as his tailored pants. Tucked into those pants and secured under a subtle but classy belt and buckle is a long-sleeved black and red Buffalo Checked shirt buttoned neatly at the wrists but with one button undone at his throat.

You do not know this man, but you know he will look perfectly in place when he arrives at his meeting, slips his blazer over his flannel shirt, and gives his presentation to his board meeting.

Now imagine the same man. He’s a little scruffy now; some stubble is growing in. The blazer is nowhere to be seen, nor is the briefcase, but he retains his belt and pants. His sleeves are now rolled up to the elbows, revealing an arm tattoo that begs you to ask for details, and in his hand is a cool beverage just served to him in a frosty glass. Maybe a second button had come undone, and his shirt is untucked on one side.

This is now a man who has worked hard all day and is now relaxing, having a drink with friends, laughing about shared memories, and leaning over the table in a languid pose. He is done with business. Now he is a man ready for a great night, and he didn’t even need to change his shirt.

Later in the week, he wakes up early to walk his dog. He will be meeting a colleague for an informal coffee in the park, so he puts on clean, tear-free jeans and a sweatshirt bearing the logo of the team he and his colleague support. As he opens the door, however, he realizes it is just a bit chillier than he had expected, and until he has his coffee, he’s just a little bit too cold.

So he takes his Buffalo flannel shirt and slips it over his sweatshirt. With the dark gray of the sweatshirt, the red of the flannel pops out to the eye, while the red and orange colors of the team logo are accentuated. He is casual and comfortable, but still tidy, still able to approach a colleague without risk of embarrassment.

That weekend, the weather takes a change, and instead of the brisk coolness of fall, there is the first frozen rain of the year. He doesn’t have long; he needs to get to the corner store and buy some de-icer for the sidewalk or his landlord will be furious. He throws on his plain white tee-shirt and slips on the same Buffalo flannel, then puts on his heavy coat and hurries on his errand.

After jogging to the store and back, he is now quite warm. As he spreads the melting pellets on the sidewalk with his heavy bomber jacket open, revealing the burst of color from his flannel shirt underneath, tempered by the tee shirt, he doesn’t look like a confident, polished, businessman. He is a working man, dressed for labor, and he wears it well.

A flannel shirt is not, in itself, a style. It is a tool to add to your own style, to let you showcase your taste and colors. Whether you wear it alone or as a layer, tucked in or loose, buttoned or not, in somber colors or bright do not let it define you.

Let it be your partner, accentuating the style you already have and love. The ways to wear a flannel are as vast as the colors available in plaid. Dressing appropriately for the season and the occasion can be a chore, but when you add in a flannel shirt, you also gain the freedom to play.

Flannel Shirt Outfits

Setting aside the story of the man with the Buffalo Check flannel shirt, incorporating a flannel shirt into your regular outfits is easy and freeing.

Start first with the look you want and add the flannel into it, as opposed to making it the centerpiece.

As a Bottom Layer

Since the Autumn of 2022 is the season of looser pants, be careful when using your flannel shirt as your bottom layer, a stand-alone shirt. Although a closely-fitted flannel can be slimming and attractive, the height of business casual attire, a slim-fit flannel with loose-fit pants will look sloppy.

Aim to use either plain flannel or a darker, subdued pattern. Wear a belt and tuck in your shirt partially, whether in the middle of the front or on one side, to accent your shape against the looser styles of this year.

Also, although your flannel is not being worn as an upper layer, don’t shy away from adding another layer over it. Make sure the other garment is longer, and preferably of a darker color. This will tie your look together and give you a sense of neatness despite being in a relaxed fit

As a Middle Layer

Furious man in bright flannel and tee-shirt.

The flannel shirt as a layer over a tee shirt is the style made popular the world over by grunge bands of the 1990s, and 90s chic is certainly in! This look is extremely versatile.

For a clean, timeless style, wear your checkered flannel over a plain white tee, paired with jeans or chinos of your choice. Look for flannel with colors that evoke the season, but that also work with your complexion and other accessories.

If your goal, on the other hand, is to express your own unique style, choose a shirt that represents what you love. Don’t be afraid of contrast! This is a style that began with grunge rock; breaking norms is as much a part of flannel shirts as is the wool its made of.

Coordinating your colors to draw attention to or from your shirt design or your jewelry, tattoos, hair, or even shoes is a great thing, but experiment with also intentionally clashing styles and colors. Unleash a bit of your inner rebel.

Make sure your flannel is at least long enough to reach your pants pockets. It should be longer than a tee shirt; otherwise, it will look like a child’s shirt instead.

For this layer, also keep in mind your environment. Flannel comes in many different weights. You can choose something very light that is more for look than anything else, and you will be comfortable through a day of work or class, but if you’re going to be moving from building to building or staying outside, look for a heavier weight that will be a functional warming garment as well as a style staple.

As an Outer Layer

Gone are the days when wearing a layer over a sweatshirt or hoodie was forbidden! When you want a touch of color or a little extra warmth even after you’ve put your sweatshirt on over your top, a flannel is a great option. There are two important things to keep in mind with this combination, though.

First and foremost: look at your fit. Sweatshirts and hoodies are already generally loose and bulky. This is why we love them! They’re comfortable and cozy and let us breathe and relax. The same flannel shirt you wore over a tee might fit, but when going over a bulkier garment generally plan to go up a size.

Try it all on and then give yourself a hug. If you can fully hug yourself without straining the seams of the flannel, you’re probably all right; just make sure your sleeves don’t look stuffed. The best outfit in the world will look ridiculous if it doesn’t fit well.

With the correct size for your outer flannel shirt chosen, look then at the colors. The overall presentation is very different here than when your flannel was a middle layer. Then, it was the agent intended to give you a slim, put-together look.

Here, as the outer shell of an already-bulky top, it can give you the look of many unwanted pounds if you are not careful. Keep your outer layer darker, at least in part, than your inner layers. Avoid those Gingham Checks unless your sweatshirt or hoodie is white, and even then, consider a plaid with some light colors, but a primarily dark base.

Even with sweatshirts, layering can be slimming and give you smooth lines, but here you want to use the outer flannel layer to draw attention to what’s underneath.

Expert Tip: Use the colors to push the eyes to the vertical opening of your torso under the flannel, not to the horizontal width of your outer layer. A darker flannel on the outside will make you look taller and slimmer, while a bright and light one will make you look wider than you are.

Flannel Shirts: Timeless, Easy Class

Although flannel shirts have been with us for several generations, they have yet to become dated. The flannel shirt itself is not dated, that is, ways of wearing it can be.

Do you want to be a walking homage to the grunge leaders of Gen-X or do you want to be daring and push at the boundaries of business attire with a bold but comfortable splash of color? A single flannel shirt can let you do both.

Unlike styles that are worn for one season and then tossed aside, the flannel shirt is versatile enough to be reused year after year, just in different ways. This fall, when relaxed pants and flannel shirts over sweatshirts are trendy, embrace it, but also let your mind wander.

Be creative. Think how you can tweak this just a little bit to be a little bit more you. The flannel shirt is intended to break the lines between classes and push boundaries. Have fun with it. Few fashion items let you play and experiment as much as the flannel shirt.

Remember: the flannel shirt is not a style to emulate. It is a fashion item to help you express your own unique style, whether that’s bold and colorful, sloppy chic, or smooth, clean, and professional. Flannel is for everyone.

How will you make it your own?

About Hugh Vinson

Hi there! My name is Hugh, and I am the owner and founder of GentlemenCenter. From Texas, USA, and with 2 sons in recent years I have had the experience of raising 2 young men. I am here to share my experiences with you, and help you with any questions you may have!

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