Flannels: How to Look Amazing in Any Weather | Part 4

Updated: May 27

We've given you the background and some styling tips for your flannel, now let's show you how to make it fit perfectly into your wardrobe and bring out your style.


Tactical Advice for Flannel Styling & Experience

Are Flannels Business Casual?

Flannel shirts come in many different colors, which makes them even easier to pair-along. You can wear your favorite flannel to the office, as well as to some other formal events. You can make it business casual by doing the following:

  • Throwing on a wool or cotton blazer on top

  • Making sure you choose the right pair of pants

  • Wearing a black tie

  • Incorporating a watch, as well as a stylish belt as your two main accessories

Should You Tuck Flannel Shirt?

If you’re going to fully button-up your shirt, you should always tuck it in. If you’re leaving your shirt unbuttoned and you are wearing a T-shirt underneath, then you don’t have to tuck your flannel shirt. Wear it as a stylish and loose jacket, since this will add to your casual look.

Style Considerations

The great thing about a flannel or plaid shirt is that they come in so many variations and they practically suit every body shape.

The flannel shirt works great as a layering piece – just team a white T-shirt and a pair of raw denim jeans with an unbuttoned flannel shirt over the top. This creates texture and adds a little bit of detail to your look, and it gives you an extra layer you can do up in case it gets cold.

For the warmer months, an oversized flannel shirt with a pair of shorts works great. Short sleeved flannels paired with boat shoes are a great summer casual look.


This is probably the way that most of us choose to wear a flannel shirt, but just because you’re being casual doesn’t mean you have to compromise on style.

You’ll probably most often wear your flannel shirt in a casual manner, so it’s important to get it right. Just because your look is casual, doesn’t mean that you can wear it with anything. If you wear a flannel shirt with sweat pants, for example, you’ll appear sloppy - stick to jeans for a casual yet fashionable look. Black jeans make a particularly stylish choice with an edgy grunge vibe, but any color can work. As for footwear, lace-up boots or sneakers are generally the best choices. Layering a flannel over a T-shirt is also a good casual look and means that you can tie your shirt around your waist when the weather gets warm. Alternatively, try rolling up the sleeves or opt for a short-sleeved style in warmer weather.

Smart Casual

A flannel shirt is an inherently casual garment, but it can also be dressed up for a smart casual look. It’s all about how you wear it and what you wear it with. Events, such as a date or dinner, can be a good time to wear a flannel shirt - just be sure to aim for a neat and polished presentation. When it comes to formal, business, or cocktail occasions, leave the flannel at home and opt for a dress shirt instead.

The smart casual look is a surprisingly good one and can create a stylish appearance. All you need to do is choose the right flannel and style it in a polished way. Start by avoiding colors that are too loud and choosing more subdued options instead. Also, ensure that your flannel is a good fit and not too baggy. Then, wear it tucked into a pair of dark denim jeans or chinos with a belt. You can also try adding a stylish wool coat or suede bomber jacket. As for shoes, choose a pair that’s neither casual nor overly formal. Loafers, chukkas, sneakers, and suede Derby shoes will do the trick.

How to Match Flannel to Your Wardrobe & Personal Style

Plaid Shirts With Jeans

The dependable flannel and jeans look needs no real introduction. It has more visual interest than a plain shirt and trouser look, but it just as versatile for most situations. Here are some helpful suggestions:

  • Stick to a slim(ish) flannel cut: Make sure the cloth weight is harmonious with everything else in consideration. Avoid wearing a lightweight, crisp shirt with 16oz selvedge denim, or a bulky overshirt with skinny jeans.

  • Wear flannel smarter: For a smarter interpretation for the casual flannel wearer, wear slim (but not too slim) grey jeans or wool trousers, chocolate brown Chelsea boots, a white tee, and a multi-colour flannel to finish it off.

Plaid Shirts With A Winter Coat

If your bosses have said their last goodbyes to the jacket and tie, you might be left in the abyss wondering how to approach the company hustle without the comfortable fall-back of the traditional two-piece suit. Fortunately, the flannel shirt can step into the breach.

This requires is a mid-weight flannel in seasonally appropriate colours, with a stiff collar. Combine this with chinos that are on the smarter end of the spectrum – a tapered leg, raised front, in a charcoal, navy, or deep brown.

In this instance, experiment with different patterns. Smaller checks, such as a gingham, tend to be less of a heat-seeker in the office. If your flannel shirt is a little roomy, trundle down to your alterations specialist to get darts inserted in the back of the shirt.

Slightly cuff your chinos so they don’t crumple at the hem, and wear a belt that matches your shoes – ideally oxfords, but boots are a definite winter alternative. This is perfect for the casual Friday.

Plaid Shirts With A Suit

You might be wondering how a flannel shirt could possibly look respectable in front of the people who determine your salary. Corporate environments, however, have been generally more accommodating of unusual ways to wear a suit.

There’s a few straightforward ways to start.

  • A pale blue prince of wales check underneath a navy tie and charcoal suit is business savvy and and a great look

  • For a wintry look, a green gingham check shirt with your staple navy suit is a solid route to adding an unusual, but business-appropriate colour choice outside the ordinary parameters of grey and blue

  • If you are tie-free, an oversized flannel check can also replace the role of a tie, by adding colour and pattern to the open gap between the jacket gorge and buttons.

Obviously, pick your battles. If the guy you need to impress for a promotion is a buttoned-up white shirt warrior, then pick a crisp, lightweight shirt with a discreet check over something bold and glorious. And if you’re wearing a thick flannel shirt, try to pair it with a suit that’s of a similar texture and density. play it safe, and test a few combinations.

Plaid Coats & Jackets

Flannels are generally heavy, so they’re a great choice for cold weather layering. A white tee, oversized green and yellow flannel, and bomber jacket is a great combination, for example, offering the right mix of ruggedness and streetwear. Keep the seasons in mind when you try this. For autumn, you might need nothing more than a flannel and puffer vest, while winter might warrant a four-layers, like a t-shirt, flannel, anorak jacket, and beanie to close off the look.

Key Takeaways "Do's and Don'ts"

  • Don’t do up the top button, so make sure that button doesn’t touch the buttonhole until you’re carefully folding it back into your wardrobe.

  • Do get a variety of options - various colours, various patterns, and various shapes (oversized, slim, and so on). Flannel shirts and their ordinary checked siblings have tremendous value in your wardrobe and can add colour and interest to even the most dull, last minute outfit you could think of.

  • Don’t combine casual flannels with tailoring, and tailored shirts with your casual ensemble.

  • Do pick seasonally appropriate colour choices. Grey and dark green are your winter staples. Lighter brown is for autumn, and then cream and white patterns for summer. These choices will reflect attention to detail, and will be harmonious with your surroundings.

  • Don’t push your luck with the flannel you wore years ago - it is worthwhile to stock up on some new ones.

  • Do pick suitable cloth weights for your environment.

The Bottom Line

What am I trying to get to in this post? Wherever you live, whatever you do, flannel shirts need to be foundational pieces in every man's closet. As you've seen above, there are rules to this game, and not all flannels are created equal. Hopefully this series has helped you to master the right fits, patterns and textures of flannel for any situation.

At Kahana, we live and breathe content creation. We love learning new concepts, exploring emergent trends, and writing about topics that foster creativity and wellness. If you're interested in writing with us or would like to collaborate for your dream business blog, we'd love to hear from you!


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