How to Wear an Untucked Dress Shirt

Image coutesy of J.Crew.


A question that is becoming more and more frequently asked as we enter into the warmer summer months and looking for a way to stay cooler is: ”Which are the best pants to wear with an untucked shirt?” As we stand facing our closets trying to put something together for our day on the go, what goes well with such a decision?

The answer is that you really can’t go wrong, provided the shirt is clean and free of large and noticeable wrinkles. The shirt that you wear should be as presentable as the rest of you hopefully is: well kept, no food stains or debris, and pleasant on the eyes. A shirt can be worn open or buttoned up, and for some individuals who enjoy a more retro and clean cut look, a t-shirt tucked in could be an option as well (a la Marlon Brando from “A Streetcar Named Desire”) . What you need to think about is what exactly you are going to tuck such a shirt into. Below are some ideas to get you untucked and rolling.


The obvious choice to make would be to play the ultimate safe card and go with jeans. An untucked shirt goes well to make the statement along the lines of “casual”. The good news about wearing jeans with an untucked shirt is that whatever the circumstance, you will fit in.

In a relaxed and laid back setting? You’re all set. Entering into an area where everybody else is dressed a little more on the formal side? No need to worry, as you’re just a few pinches away from matching their level by re-tucking in your shirt, and unrolling your shirt sleeves.

Just make sure that the color of your jeans is a dark color, as lighter colors tend to appear much more casual and laid back than their darker constituent. When in doubt for what to pair anything with, start with jeans.


A common mistake that the world has decided to forgive is that pants that are not jeans, but not slacks or sweats either is called “khakis”. The exact term that is left out in the cold is “chinos”, despite what your mother calls them.

Chinos are durable, flexible, breathable, and available in every color and shade under the sun (even khaki, which is a color), so you definitely want to procure a pair of these bad boys whenever you can.

When you want to pair them with an untucked shirt, simply go for it! Just like jeans, you can dress up or dress down with chinos, and just as easily re-tuck your shirt in if you need to instantly dress up your ensemble. All you need to do is pick out the right color to match your untucked shirt, and that’s all there is to it.

For a more casual look to go along with your untucked shirt, consider rolling up your pant legs about an inch or so. Nothing says “I’m not working today” louder than showing off a little ankle.


Shorts used to be a no-no in the fashion world, but since have come back and been relabeled as playful “pants alternative”. Shorts today have several different options that vary from fabrics, patterns, length, and color. Depending on the kind of shorts you are looking for, you can easily pair your untucked shirt with whatever you have in mind.

The easiest way to decide what kind of shorts work best for you is to think of them as chinos (like the ones we mentioned above), but just shorter in length. Shorts and chinos are usually cut from the same kinds of fabrics and crafted by the same manufactures, so there really isn’t going to be too much of a difference between the two, making your choice of shorts easier for you.

Just don’t wear jean shorts. Seriously. Just, don’t.

Dress attire.

Untucking your shirt, even when trying to appear more formal, is definitely a statement. A well fitted blazer, slacks, and a pair of choice wingtips can be all you need to elevate your look, and by untucking your shirt you are simply adding a little personality to your ensemble.

The only rule here is that your untucked shirt must not be longer than the length of the bottom of your blazer of jacket. If you can see the back of your untucked shirt hanging out from under your blazer, it’s too long, so tuck it back in or change to a shorter length shirt.

UNTuckIt, a men’s and women’s  shirt design store based in New York makes shirts designed just for such occasions, with all of their button down shirts and polos designed to left untucked. Interested in pursuing a life all about hanging out? Check them out.


With so many options for what you can pair an untucked shirt with, it’s hard to make a mistake. As long as both your shirt and pants are cleaned and wrinkle free, you should be able to make it through the day looking relaxed, casual, and most of all – sharp.


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