Tucked Versus Untucked Dress Shirts

Untucked Vs Tucked In: Dress Shirts

The untucked dress shirt is a time-honoured tradition for those who don’t know how to dress. These types usually think that merely untucking their shirt after a long day, or throwing on their favourite work shirt with a pair of jeans, passes as “cool” and “casual.” I am here today to tell you that everything about that line of logic is wrong. It’s worth mentioning when I say dress shirt, I mean a formal dress shirt and not a sport shirt, we’ll talk about the differences through out this article.

As you have probably gleaned from my tone, this is something that annoys me deeply. I want to call it lazy, but that’s not necessarily true; it’s more than that. Standing and looking at oneself in the mirror and thinking that it looks good shows a deep misunderstanding of what dressing well looks like. It’s a fundamental misstep when putting a look together, and an unfortunate sign of things to come. Once the untucked dress shirt becomes acceptable practice all things are lost.

Fortunately, I am here to help correct any errors and poor sartorial thought processes. Since this move seems to be quite pervasive, let’s do our best to tackle how to change this line of thinking and what some significantly better alternative look like.

There’s a chance to come back from this fellas, I promise. A shove in the right direction is all one needs to be set on the right path, and we can find that path. Let’s discuss how we can avoid thinking this works and how we can do better. Let’s all do better, shall we?

Tuck In Your Dress Shirt

Untucked Dress Shirt. Top Looks Good, Bottom left super sloppy, bottom right greatUntucked Dress Shirt. Top Looks Good, Bottom left super sloppy, bottom right great

Img Credit: Proper Cloth, A Hacked Website, Executive Style
Top is an example of a sport shirt, or a casual dress shirt or however you’d like to call it. That dude is killing it because his shirt is the right length. The grainy photo in the bottom is what we want to avoid. That is clearly a dress shirt. Tuck it in. Lastly, we have this dapper gent in the bottom right who knows when to tuck it in.

Yes, this is an extremely simple way to avoid this problem. Anytime you think, “hmm, maybe this would look better untucked,” don’t. It’s an easy fix to an easy problem. Your shirt untucked will never look as good as it does when it’s tucked in, and there are  numerous reasons as to why.

First of all, your dress shirt is too long and will look stupid untucked. It’s not some next-level style move to layer with different proportions when you’re doing this. The reason your dress shirt is so long is because it’s supposed to be tucked in while giving you a bit of breathing room. It’s going to look long and sloppy untucked.

The second reason it will look bad is because the front and back portion of the shirt that should be tucked will become comically wrinkly. Every time you sit down the shirt will scrunch up and wrinkle, making your shirt look increasingly ridiculous throughout the course of the day.

Typically, when wearing a dress shirt, frumpy isn’t the desired look you want to project. Tucking your shirt in will help to avoid this misstep.

Mind Your Proportions:

Men who dress well traditionally do so because their proportions and fits are spot on. Sure, you can play with colour and pattern and all that stuff, but if your proportions are off than your look will look off too.

A dress shirt is meant to be tucked in because it’s meant to act as a compliment to your trousers, shoes, and jacket/sweater, should you choose to wear one. Especially when worn with a suit, as the jacket and pants have been cut to compliment each other and be of equal proportion. When worn with an untucked dress shirt, it completely throws off the balance of the look. (I realize this is more of a casual look, but it’s worth mentioning as I have seen this enough times to talk about it.)

The same logic applies when you’re wearing jeans or a more casual pant. Skinny pants and an untucked dress shirt looks off because the proportions haven’t reached a stylish equilibrium.

Unless you’re someone who’s into street style and takes their queues from that section of people, stick to what handsome men have been doing for decades, which is to dress in clothes that fit and wear them the way they’re supposed to be worn. I can tell you that Steve McQueen never dared untuck a dress shirt at a casual event.

Casual Dress Shirts, That You Can Wear Untucked

Where most men stumble here is that they don’t know what works in a setting that calls for dressy/casual or some other equally stupid oxymoron. That I can understand, because traversing the vast network of event dress codes is a fool’s errand. The best alternatives are known as “sport shirts,” or just casual shirts with collars. Yes, this is a very non-descriptive way of telling you what to buy, but we can use a few rules of thumb here to help narrow the field.

  • Does it have collar stays? You know those little plastic inserts that keep your collar stiff? If it has those it’s a dress shirt and should never be worn untucked. If shopping for a casual shirt, you can immediately eliminate any shirt that has stays.
  • How long is it? A good rule here is that if the back portion of the shirt falls below the half-way mark of your butt, it’s too long. The front should be around where the pockets of your pants begin. Again, dress shirts are cut much longer to be worn tucked in, and sport shirts are cut shorter to be worn untucked. If you’re unsure, ask a sales person or someone else around you. a second opinion never hurt anyone.
  • How would it look with a tie? If your immediate reaction is “weird,” than you’re probably on the right track. Sport shirts aren’t meant to be worn with ties, and their collars probably don’t have the structural integrity to house one. This is a bold style move for some, but for the rest of us, if the collar looks weak, then don’t add a tie to the mix.

Wrapping it Up

While you may see guys out there pulling this move off successfully, it’s probably because they’ve mastered the art of proportion and are actually, you know, cool guys. To say that no one should do it ever would be wrong of me, but every regular dude out there should stick to what he’s best at; you’re not Bruce Pask.

Untucked Dress Shirt? Only If You're Super Cool

Img Credit: Le 21eme
Bruce Pask. Being super cool, without trying.

I know this comes off as harsh, but think of it as tough love. Sometimes we all need a little kick in the butt. Hopefully going forward when you get kicked in the butt, that person will hit your pants because your shirt has been tucked in properly. Like a gentleman.

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