Un-tucking your shirt does not hide your belly, and in fact, it makes it look worse because what happens is that we all see that you’ve just un-tucked the shirt. It’s usually wrinkled there at the bottom. It draws attention to that area.

If the shirt is too long, which for most guys, they do wear that shirt too long when they try to wear it untucked, it looks almost like a dress. And we see these stress marks around your stomach.

It just doesn’t look good. Realize that most shirts that are colored are designed — I’m talking dress shirts here — are designed to be worn tucked in and they’re going to look best when you wear them like that, even when you have a little bit of a stomach. Yes, you’re going to be able to see the profile, but you need to own your look.

Confidence is going to take you really far. And yes, I know a lot of you guys are carrying a little bit of extra weight, but you need to throw it out there and say, If you want to eliminate or hide a little bit of the midsection weight, you have to add size to the shoulders, and the only way you’re going to do that is with a jacket.

There are some shirts that add a little bit if you’ve got epaulettes, which are leftover or a vestige from shirts of military origins.

Those help a little bit. They kind of build up the shoulders and kind of create an illusion, but overall, most shirts that are not designed to be worn untucked are not going to look good untucked on a man. They’re just going to make you look sloppy.

I’ve hit that out there. Most shirts are designed to be worn tucked in. If you have a belt and it has belt loops and you’ve tucked in your shirt, remember to wear a belt with that. Don’t not wear a belt.

There’s a little bit of a trick. If you want to look a little bit better, you want to look taller, one thing you can do is choose a belt that doesn’t contrast the trousers.

If perhaps you’ve got a really small upper body though and you want your upper body to look a little bit big, go with a contrasting belt buckle or contrasting belt and that’s going to actually make your torso a little bit bigger.

Another thing is to make sure you properly tuck in our shirt. You don’t want to just throw it in there. You want to put it in there properly.

Well, there is an actual style that’s more a casual shirt or polo shirts or t-shirts. Those are made more to be worn un-tucked. Now, you can tuck in a t-shirt and you can tuck in a polo shirt, and you can tuck in some casual shirts, but these are going to be the shirts, not dress shirts, that are made to be worn un-tucked.

The big thing, if you look at the bottom of just most polo shirts, you’re going to notice that they look different than the bottom of a dress shirt. The bottom of a dress shirt usually has, in the front area, it goes down low and in the back area, it goes down low. Here on the sides, it goes up. You’re not going to see that on polo shirts.

On polo shirts, you see where the front is straight across and in the back where the two pieces of the shirt have been brought together. The back is maybe a little bit longer. That indicates that this is a shirt that can be worn un-tucked. It doesn’t have to be, but can be.

Proper Fit and Length of Shirt

Another thing you’re going to want to make sure is that the shirt length is right for you, so have at least two inches enough so that whenever you raise your arms up, you’re not going to expose your midsection, but you don’t usually want to go beyond four inches.

This is a proportion thing because if you’re 6’8″, you’re going to want to lean definitely towards the four inches. If you’re 5’2″, you’re going to want to lean towards the two inches and be very careful about that because it’s proportions and what’s going to look good.

What you don’t want to have covered, you don’t want to be covering your crotch area or you don’t want to be covering your back side with the shirt as it goes down. There are a few exceptions. One of them, I’m drawing a blank here, but I’ll link to it down below.

It came out of Cuba and a friend of mine down in Miami makes these very specialty summer shirts made for hot weather wear. They’re called the Mexican wedding shirt. I can’t believe I can’t remember this. In any case, I’ll link to them down below, but those are one of the few shirts in which you should wear them untucked and wear them longer.

Another thing is to wear them with the right type of clothing. The gentleman in the question is talking about dress pants. Dress pants, you do not wear untucked shirts with. You just don’t do it, with jeans, with shorts, with casual clothing because untucked, when it comes down to it, is a casual look. It gives off a casual feel, so make sure the clothing styles are right.

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