Is it Okay to Wear a Flannel Shirt with Khakis?

“Beauty is a mystery. You can neither eat it nor make flannel out of it.”

With an innate fashion sense somewhere between Cro-Magnon and post-apocalyptic survivalist mode, I’m the perfect person to ask about style.

Fashion is something I greatly enjoy, and when I do notice what someone else is wearing, I’m either overwhelmed by a sensation of being completely out of touch, or on occasion, (very rare occasions I might add) I’m delighted to see I’m in lockstep with the latest fashion trends.

When it comes to whether you can wear a flannel shirt with khakis, the answer is obvious, sure you can, who is to say you can’t?

I evolved a bit from childhood when getting the kitties and bunnies to match on my shirt and pants were my first training in fashionable attire, to today when my fashion sense is completely my own unless my wife stops me at the door, and demands I change.

She can spot the slightest flaws, maybe something as innocuous as a motor oil stain on a sweatshirt or a hole in my favorite flannel shirt. She’s a taskmaster that one.

FYI, thanks to AI imagery software, we’re able to create very specific fashion examples to illustrate the points being made.

Flannel and khakis

What could be more natural than this combination? Soft cotton, easy living on both sides of the beltline.

Flannel exudes an image of laid back relaxation, something we don’t get nearly enough these days when life seems to get ratcheted to higher, and higher levels of anxiety with each passing day.

A flannel shirt gives you an excuse to buy larger size pants. Depending on the weight of the fabric and how tight you like to wear your pants, a flannel shirt adds enough volume around the waist to wear a size up. More space, more comfort, especially in khakis which are the modern bridge between sloth and business attire.

Is it ok to wear flannel shirts and khakis?

Is this even a debatable question? Of course, it is, flannel shirts and khaki pants are mom, apple pie, and Chevrolet all woven into a simple cotton fabric. They are the essence of leisure fashion.

A flannel shirt has a collar, so even if you find yourself dragged into one of those preppy establishment that require you to wear shoes, a shirt, and other unreasonable dress codes, you meet the standard.

The host might give you a snotty sneer when he spots your fashionably plaid red and grey flannel shirt over your light tan khakis, but what do you care? If you spill a little sauce eating ravioli on your shirt, who cares? You sure don’t, you’re wearing flannel and khakis.

That butter from the spilled lobster dipping cup on your khakis will wash right out, that’s another benefit of this most fashionable of wardrobe attire. It’s cotton, it’s machine washable and you don’t have to take it to the local dry cleaner and do a lot of explaining on why the stain is there, to begin with.

Ubiquitous attire for the man on the go, or the man with no place to go

Khakis bridge the gap, (can you get them at the Gap?) between those incredible, old, torn, faded jeans that you love.

Odds are your wife won’t let you out of the house when you’re wearing them, but they remain your favorite pants. At the other end is that annoying pair of dress pants, the ones that pull funny at the pockets, that are always shrinking in your closet while they wait for months or years to be worn. Those annoying pants that you’re goaded into wearing with a dress shirt, jacket, and a tie that makes you feel like Clint Eastwood swinging from a tree in Hang ‘em High. 

Just the thought of that constricting attire makes you want to run for the cave and a nice comfy bear skin.

Khakis give you the comfort of those old jeans, with the bare minimum requirement of formal attire. You’ll get looks, but who cares, those khakis with an open dress shirt and sports jacket get you in the door. Those crossfit shoes, even if they’re black, probably won’t be allowed out of the house but khakis fit just fine over a pair of boots if you buy them big enough.

Flannel – the working man’s fabric

Your flannel shirt won’t make the cut at that formal dinner or some snooty restaurant where they never give you enough free bread, but it’s also a gap piece of clothing.

My preferred attire is a t-shirt and jeans or a t-shirt and shorts, but khakis work well with t-shirts too. Maybe a t-shirt with a college mascot on it, some hunting apparel company, or even better, a wise cracking comment that removes any doubt from strangers that there is something wrong with you.

Wives don’t like those t-shirts at home and are repulsed by them in public (as if you had a chance of getting in the truck to go out wearing one in the first place).

Button down collars, tight cuff dress shirts that constantly pull out of your waistband are as bad as the pants, jackets, and strangulation devices they were designed to go with.

A flannel shirt meets the minimum requirement. It has a collar, you can tuck it in, it has buttons on the cuff and it goes with your khakis, there is so much winning in this combination that there is no competition.

Conclusion

Flannel shirts and khakis have been with us since the 50s, they might have called them chinos then, but they were khakis. Comfort style, the ability to meet ridiculous standards of dress, and the wearability usually only found in jeans, shorts, and t-shirts all come together with a nice clean pair of khakis, and a flannel shirt you haven’t ripped a hole in or spilled oil on yet.