You're finally wanting to move out of that flannel shirt wearing phase, we see. While those are great to wear, they are not always the best thing to wear to a business or professional environment. However, we know you want to keep things casual while also being professional. This can be accomplished with an untucked dress shirt. Many may then rightfully ask how to wear a shirt that isn't tucked properly.

We totally hear you on this, as it can be hard to put together an outfit only to have an untucked dress shirt that just won't work. Honestly, most dress shirts are made to tuck-in. If this is the case by design, then what can you do to look good in one? This is not exactly as hard as some make it out to be, yet you'll need to pay close attention to what we advise.

How to wear an Untucked Shirt

We're not here to steer you wrong, so check out these tips and tricks to help you wear an untucked shirt like you just don't give a f&S%!

How Long should an Untucked Shirt Be?

While we will go over this a bit more in the cut options, we should certainly highlight the length of your dress shirt before we go too deep into how to wear an untucked shirt.

It should be obvious that if you have a longer dress shirt, this will not work very well untucked. This is similar to even a long t-shirt or Polo shirt. If the shirt is too long, you're going to have an issue with this.

We find that men who buy sizes with freedom tend to buy shirts at the incorrect size. They may not have a six-pack body nor are they very big. Yet they will get a slightly bigger shirt because they feel those at their size are too restrictive.

This can be an issue for a lot of guys. Naturally, they buy the shirt at a larger size and know they can hide the length of it as its tucked in. Meanwhile. the arm length can be hidden with rolled-up sleeves or a jacket over it. Yeah, we know your tricks, Steve!

As a result of this, these shirts cannot be untucked.

However, we recommend instead of doing this that a man considers the material on top of the measurements of the shirt. Certain shirts are made differently compared to others. This can affect not only the sizing but also the length.

For example, some men are a Large in the J. Crew line but happen to be an Extra-Large in the Brooks Brothers line. This may differ in each depending on the cut but this isn't uncommon to see. It happens in jeans all the freaking time!!

Therefore, trying other types of shirts on and seeing how they will work for you can be great. If you still have an issue, a tailor can help you out.

Mind The Cut

A lot of dress shirts are made to tuck into dress pants. As a result, you need to find the ones that can be tucked in but also those that can go untucked too. Most of these shirts will be those with compelling patterns, which we'll discuss more later in the article. The cut of the dress shirts you can wear untucked will vary, but the most important thing to pay attention to is the bottom of the shirt.

Those that look best untucked will not have what we like to call "hip slices" in them. You know what this is even if our name for it is unfamiliar. It is the type of shirt that will have a long front-end and a long back-end. Yet on the sides, you'll see a round half-cut curve present that's almost exactly even with your hips. Hence, "hip slices."

These are the type of dress shirts that must be tucked in or they'll end up looking weird. If a shirt has a small hip slice that is not prominent, it may very well work. You will also need to look out for those with a rounded-out front and back, as those will also not work if these sections are relatively long.

You'll likely have the most success with slim-fit or fitted dress shirts in this area. All of these dress shirts are made to work for a certain look a man will have. As a result, the slices and rounded-out areas will never be too long in shirts. like this. Usually, a man who buys a shirt that fits like these will usually be at the exact height needed to keep this from being an issue.

The real areas to be careful with this are the Relaxed as well as the Big & Tall sections.

What Material is best for an Untucked Shirt?

A lot of dress shirts are made with some interesting materials. Cotton, Polyester, or a blend between those two tend to be the most popular. This is due to the affordability of these options over others. Yet Oxford fabric, as well as Silk, will usually cost a bit more. The big thing to consider with all of them is that certain fabrics are also easier to pull off the untucked look with.

The reason for this often has to do with how the tail-section looks. If you're going to wear a shirt untucked, it seems Silk & Oxford tend to have the most shirts that can work well. This is likely because the tail sections on silk are never going to be bad....cause it's silk. Meanwhile, Oxford dress shirts tend to be made with the concept that the shirt will be worn tucked and untucked.

Cotton, Polyester, and the blend of the two can be a real crapshoot. A lot of the dress shirts made using these materials aren't cut well at the tail sections, making the shirt look kind of awkward. However, Twill shirts tend to be the worst with this. Twill dress shirts are seemingly made to tuck-in it.

Fine Cotton, however, you might be able to get away with untucking. It all depends on the length you end up getting. Pure Polyester shirts may not always look great untucked, but there is a solid chance any version of this will be either-or. The more expensive type has the best chance of being tuck or untuck.

What Patterns are best?

Pretty much any shirt with wild or compelling patterns will work as a tucked in or untucked shirt. However, we have never seen a dress shirt with a graphic on it that isn't possible to wear untucked.

One of the most popular options when not tucking is the checkered or striped dress shirts. For some reason, these shirts are almost made specifically to be untucked. While many are capable of one or the other, you'll come across others that will just work best untucked. These shirts tend to be the pattern button-down types.

Those with graphics are the best to do this with more than others simply because they are made to use with a professional and casual environment. You can wear those with dress pants as well as jeans and even shorts. Therefore, you want to search for those types of shirts.

This can also be accomplished with solid color dress shirts too. However, we find that the best solid color dress shirts are often made from Silk or Oxford fabrics. Sometimes Linen works here too, but that all depends on who makes it.

We find that the brand simply called UNTUCKit has the best overall option of dress shirts made to be untucked. They have the best overall options that include all types of shirts, including those of multiple fabric types and colors for any shirt meant to be worn untucked, including many wrinkle free options.

Should you fully button an Untucked Shirt?

With the best options for untucked dress shirts, you'll be able to button them up and wear them like that or unbutton them without either looking weird. This is something you can easily see when trying on the shirt at your local store. Simply go to a dressing room to check on this. We recommend keeping your t-shirt on while doing that, however.

You want to do this for two reasons. The first is to see how a shirt will feel underneath the button down dress shirt, because you may want to wear an undershirt with it. Second, you want to see how a shirt will look untucked with another shirt underneath.

A nice shirt and short sleeve t-shirt underneath is something casual that untucked shirts will be able to pull off well. Therefore, this is a good way to try out a dress shirt before buying it.

On a side note, keep in mind that others may have tried on that exact shirt. So exposing less of your skin to it than you have to before buying and washing it is smart to do. Let's be honest here, with all of these viruses going around, you can never be too careful, right?

What Are You Going To Wear It With?

We have sort of highlighted this throughout, but have not yet put it in its own section. However, this is a good question to think about, particularly if you are in a business casual setting. What are you going to be wearing your new dress shirt with? Also, what is the main environment you're buying this dress shirt for?

Naturally, it saves money to buy a shirt that can work well tucked or untucked. However, if you're never going to be in a professional environment to need this and only need a dress shirt for dates or random weddings, then finding one that makes more sense to untuck is the smarter option.

Are you considering a tie with your dress shirt? While we do not recommend this, some updated fashion types seem to believe this works. Especially with solid dark shirts with brighter color silk ties. We do not recommend it, but if it looks good on you...by all means, live your truth, Captain.

The greatest untucked shirts for men will work well with jeans and sneakers. They will work well as the sleeves are rolled up and can work as both professional and casual. They will also be easy to wear with various belt types too.

There are shirts out there that can do all of this, but it's up to you to find them.

However, we feel we have done pretty well with helping you out here. Go forth brothers in untucked shirt arms and find the dress shirts that work best for you. If you need us, we'll all be here with our shirt untucked...like a motherf&$%ing boss!