Men’s Guide to Properly Tucking Shirts

Tucking your shirt is not as easy as it seems. Mess this up, and you’ll be less confident all throughout the day. This may be just a small detail in your outfit, but it can ruin your entire look. 

What are the rules then? Here are three helpful tips for you:

Before anything else, do understand that there are 4 out of 5 situations that might require a tucked in shirt. May sound like a lot, but this is based on the assumption that men always have collared dress shirts in their wardrobe and most of these look better when tucked. 

How about the 5th situation? Remember, there is no bad style as long as you are wearing it right, the same with your untucked shirt. 

1. The first thing we need to identify is the type of shirt you are wearing.

– Short, even hem  like the ones in polos and shirts are meant to be untucked

– Uneven hem with front or back tails that meet on the sides of the hips are meant to be tucked

While there are many variations such as longer in the front but shorter in the back or awkward long even-hem shirts, most men shirts are easily identified at a glance. Follow the general rule, and you’re all good. 

Sure there are some exceptions but are mostly limited to subculture-specific looks such as country rockers with tucked in shirts and big belts. No denying, it’s quite a look but if you’re not part of that picture, better not go with it. 

Below are the common types of men’s shirt and how they should be worn:


– T-shirts

– Polo shirts

– Rugby shirts

– Henley shirts

– Short-sleeved, button-fronted sport shirts

– Tank tops and other sleeveless shirts

– Breton tops

– Guayaberas

– Hawaiian and other vacation shirts

– undershirts (but tuck if the alternative’s hem is poking out)


– dress shirts

– long-sleeved, button-fronted sport shirts

– flannel and chambray work shirts

– wool “lumberjack” shirts

2. Identify if the shirt’s design is meant for tucking or not.

Getting the right fit for an untucked shirt is very important since shirts of this type look looser than a tucked-in one. Sometimes, it may be too baggy and quite a challenge to correct. 

Here are key points to look out for:

Shirt length

Obviously, the length matters. You can’t tuck a shirt that’s too short, and you also can’t keep a long shirt untucked. 

The basic rule is if the shirt doesn’t fall to your belt, it’s too short. If it covers all the way down to your crotch, the shirt is just too long, or it’s a short dress. 

If the shirt is in between, well, you’re all good. Ideally, it should cover the belt but not much more beyond that line. 

Shirt waist and chest

Casual shirts are usually tapered at the waist. Basically, they are also meant to be worn untucked. You may want a close fit through your torso but not too much that your body gets too hugged by fabric. Most shirts also don’t come in numeric measurements so you will be stuck on the S, M, L and so on. Some sizes also differ from one brand to another. You might fit Small in one brand, but another brand calls for an M. In that case, just choose something that is not too tight with your nipples poking through. 

Shirt shoulders and sleeve

Of course, how would you go around wearing shirts with sleeves that are either too tight or too loose? Come on, they’d look silly you know. Take note. If the shoulder seam goes halfway to your bicep, don’t wear that. If it goes all the way up, don’t wear it. If you want to show off your biceps, better go sleeveless. 

Tailed shirts

Nowadays, you will see younger guys wearing an untucked shirt with long front and back tails. You can see it anywhere and in catalogs. But, this look is a sloppy, I-don’t-care look, and kind of unconventional but some do look good with it. Otherwise, they just look lazy. 

If you are one who wants to try it, look at yourself in the mirror first. Just scrutinize how you look and what it would imply. 

So, that’s all for untucked shirts. If you have any idea on your own, you can absolutely try your own style. As long as again, you are comfortable, and you don’t look silly. 

3. The formality of the event

As the general rule of the thumb, never wear an untucked shirt to a formal event, unless it is designed to be formal and untucked. The Guayabera is an example of this style. Otherwise, formal attire means tucked, plain, and simple. 

Shopping Cart