Style Dilemma: Should a Flannel Shirt be Tucked or Untucked?

So you’ve picked out your outfit, from the shoes to the pants, to the belt, to the shirt. But once you get it on, you could find yourself faced with one of the most common questions men ask when finishing up with the final touches: Should I tuck in my men’s flannel shirt, or should I leave it untucked? It may seem like an easy question to answer, but there are a handful of factors to keep in mind to avoid looking like a stuffy nerd or, worse, like someone who couldn’t care less about his appearance. If you want to look great in your favorite flannel and make sure you wear it right, read on.

How the Most Common Types of Men’s Tops Are Worn

For an overall, basic idea of how most men wear their tops, here is a quick rundown on what those shirts tend to be, and whether they’re worn tucked or untucked. Tops that are traditionally worn untucked include T-shirts, Henley shirts, men’s polo shirts, rugby shirts, short-sleeved sport shirts, tank tops, and Hawaiian shirts. Tops that are traditionally worn tucked-in include long-sleeved dress shirts, long-sleeved sport shirts with a crew-neck collar and flannel shirts. Like with anything, however, there are exceptions to the rules.

Start With the Hem

When considering whether to tuck in your flannel shirt, start by looking at the bottom hem. If the hem is short and straight, it is likely made to be worn untucked. In fact, it may not look good at all if tucked in. In contrast, if the hem is uneven and has a longer front or back, it is made to be tucked in and will look good that way.

If the shirt has an uneven hem but fits you well untucked and flatters you, it may be okay to wear it untucked if it is the right length. Ideally, it should reach the middle of the front zipper of your pants or the middle of your back pockets. Fabric matters too. If it is soft flannel, it may look great untucked if you’re going for a casual look. In contrast, a more formal men’s dress shirt with an uneven hem may make it appear like you missed a step when you got dressed in the morning.

Consider Your Destination and Audience

Considering where you’re going and who you will be seeing before deciding whether to tuck in your flannel shirt isn’t as easy as it may seem. For example, if you’re meeting your significant other’s parents for the first time and want to make a first impression, you could look too stuffy tucking in your flannel shirt if they’re watching football on a Sunday afternoon having wings and beer. In contrast, untucking it if you’re going out to eat, even at the most casual places, could make you appear that you don’t care about making a good impression. Think about your audience. Are they laid back? Are they more formal or polished in their appearance? Think, “Would they be tucking in their shirt today?”

Another example of when your destination and audience might not help much is when it is casual Friday at work. Your co-workers might leave their flannel untucked and it might be perfectly acceptable. But when you’re all riding in the elevator with the CEO and you’re the only one with his shirt tucked in, you’ll be more likely to leave a good impression. The choice is yours.

Are You Dressing in Layers?

If you plan on wearing a sweater, leather jacket or blazer over your flannel, tuck it in. Although leaving a bit of the bottom hanging out can be a good look, it’s a little too risky unless you’re confident it works. If you plan on wearing a T-shirt under your flannel shirt, you could go either way: tucked or untucked. It all depends on the look you’re going for. If it is a rock concert, don’t you dare tuck it in. If it is happy hour after work or a hot date, tuck it in. Of course, you’ll need a nice belt with those men’s pants as well, so be sure it is in a color or material that complements the flannel.

Flannel has come a long way since gaining its reputation as a “lumberjack” shirt. You can look quite polished with the types of flannel shirts available these days, especially if you tuck it in, no matter what time of year it is. Regardless, the choice is yours, providing you stick to the rules mentioned above.