OK – Don’t listen to your roommate’s opinion on whether to tuck your shirt in or not, take it from us! Choose not to tuck your shirt in the wrong situation and you risk looking sloppy or lacking class; choose to tuck your shirt in the wrong situation and you risk looking silly or stylistically challenged. This simple decision can make or break the situation, whether on a date, at a social function, or casual Friday at the office.

When it comes to tucking your shirt in, the rules are generally easy. Most cases will serve you well to keep that shirt tucked, but there are some things to consider as you make this important but relatively simple decision. It comes down to three considerations that we will lay out for you here:

What kind of shirt is it?

For some, it will be easy to tell whether the shirt is meant to be tucked or not, and for others perhaps not so easy. For the latter, take a quick look at the hem on the bottom of the shirt. If you notice that the hem is consistently even all the way around the bottom of the shirt, it’s likely that the designer meant for it to be worn untucked. However, if the hem is uneven in any way, the opposite may be true and you should consider tucking it in.

There will be exceptions to this rule. For example, button up shirts are generally meant to be tucked, but there are companies making button up shirts with a more even hem that have been designed to fall at a comfortable length when left untucked. These are generally marketed as such, so you should be able to clarify this easily.

Generally speaking, here are some examples of how shirts should be treated:

Untucked

• Tee Shirts
• Polos
• Rugbys
• Henleys
• Short Sleeve Button Ups
• Tanks
• Bretons
• Guayaberas
• Hawaiians

Tucked

• Business Button-Ups
• Long Sleeved Button-Ups
• Flannels

How does design play into the equation?

First of all, a little bit about fit… The correct fit is key to any shirt, whether you plan to tuck it in or not – but especially if you intend to leave it untucked. When tucking a shirt in, you can pull back some of the extra fabric if it is a bit large, but when leaving it untucked you can get swallowed up by a shirt that is too big for your frame. Now that we have covered buying shirts that fit you, let’s take a look at the details.

Waist and Chest

The shirt should fit nicely against your torso – that is not too tight but it shouldn’t look sloppy and large either. You won’t find very often where a shirt is tapered below the chest, though some button ups are offering more of this as the fitted and tailored look is becoming more sought after. Many times you will have to choose between small, medium, and large, so it is a good idea to try shirts on before you purchase them to make sure that they fit well through the chest and waist.

Length

This plays heavily into whether you will be able to tuck it in or not. If the shirt is too short, it will look sloppy as it comes untucked each time you twist, sit, or bend over. It needs to fall below the waistband to be considered for tucking. On the other side of the spectrum, if the shirt falls to the crotch or lower, it’s going to be tough to get away with not tucking it in as it is falling at risk of looking like a dress. Somewhere between the waistband and the crotch is the target area for any shirt you plan to wear untucked.

Shoulders and Sleeves

As long as we are talking about the correct fit for a shirt, we would be remiss if we didn’t mention that it is critical to ensure the shoulders and sleeves are correctly proportioned to your body. The shoulder part of the shift should end about the end of the shoulder bone, no shorter but you can get away with slightly longer if needed. As for sleeves, too short and you end up looking like you are trying to show too much arm; too long and your shirt just starts to look silly. For a long sleeve, it should fall to the end of the wrist as the arms hang at your sides.

Tailed Button Up Shirts

Generally speaking, again, these will be tucked in and bought to fit nicely. Now, if you take a look at any college campus or social gathering where t-shirts are a bit passé, you may see a tailed button-up worn untucked. Though it is possible to pull this off, you will have to make the determination as to the situation and the length of the tails on the shirt. Some are so clearly long that you will look ridiculous trying to pull it off, but there are some that you might be able to get away with. If you like this look, check out the company Untuckit, they manufacture nice button ups that are tailored specifically for wearing untucked.

What will be the Situation or Environment?

Take very seriously the type of situation that you will be in. This will help you decide not only what kind of shirt to wear but also whether to tuck it in or not. In a casual setting with friends, you can leave a polo untucked. You can also dress a polo up with tucking it in and pairing it with a nice belt and shoes if you are on a date or meeting her parents for the first time. When it comes to formal events, always err on the side of a nicely fitting, button up shirt that is definitely tucked in. Depending on the level of formality, you will also take into account the colour and whether to pair and tie or a jacket (or both) with it.