A tie with an UNTUCKit shirt?

Q. Is there a specific variety of tie and, when appropriate, jacket to wear with an UNTUCKit shirt as opposed to a standard dress shirt?

A. My first response would be none, none, and none. That is, no, you should not wear a tie with an UNTUCKit or other brand of untucked shirt. So, no, wearing it with a blazer-and-tie combination would also not be appropriate. And, I would like to go further and say, no, you should not wear those shirts period for work, but times are changing and I'll adjust my advice a bit to be more current. There are certainly many companies where a large number of men, including bosses, will be happily wearing them.

For those who are unfamiliar with the UNTUCKit brand of shirts, it is a retail company that specializes in selling men’s casual shirts that are designed to be worn untucked. They are a form of button-front shirt that is cut very much like a dress/business shirt, but with a difference. The main points of distinction between these shirts and standard men’s shirts are that they are shorter, somewhat more fitted, and have shorter and less-pronounced curved shirttails that end at a point that exposes part of the pants’ pockets. Although the actual difference in inches is slight, it is visually noticeable, especially to those many men who like wearing their shirts untucked. Another point: these shirts are also designed to be worn unlayered; that is, not underneath and extending below a jacket or sweater. The quality and price of the shirts is upscale. They are available online and in their own brick-and-mortar stores.

Some elements of men’s clothing are designed to work well together. They include a suit and tie, navy blazer and gray trousers, sport-shirts and jeans, T-shirts and shorts. These pairings all make (appropriate) sense.

Similarly, some elements of men’s clothing are not even logical when worn together. They include a tuxedo with sneakers, white socks with a dark dressy suit, wildly clashing colors and patterns such as plaid pants with a polka-dot shirt. A reasonable comparison that I would be perfectly willing to accept is with polo shirts. You would not wear them any time a tie seems appropriate, such as when you’d wear a suit or blazer, but you could wear them appropriately with khakis, jeans, and shorts to most casual and at-home occasions.
       
Certainly, our clothes are supposed to make us feel comfortable. But – in the eyes of those making the rules and those you meet who expect you to follow them – that does not give us permission to choose combinations that insult and offend the eye of the beholder. We are all taught early on to use our strengths to help us succeed. Why deliberately choose obstacles that detract from our appeal when it is easy to pay just a little extra attention and make attractive choices?
       
The truth is that the idea of wearing a shirt that is purposely designed to be worn hanging out is a rather brilliant marketing strategy. It is a form of permission that many men want, allowing them to dress more casually. In light of the rapidly expanding number of UNTUCKit stores that are popping up around the country, the appeal seems to be widespread.  However, I believe you should tuck it in when wearing one of these shirts with a blazer; and then you might just as well wear a traditional dress shirt and avoid the annoyance of it’s perhaps pulling out every time you sit down.
       
Finally, to provide one more comparison, it is likely that the interest in these shirts has some of its origins in Habanera shirts and Hawaiian shirts, both of which certainly are not tucked and are usually considered a big step up from T-shirts in formality. Even so, they are not traditional office wear unless you are Magnum P.I. . . . 1988 or 2018.

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