Wondering What to Wear . . . with Michael Strahan

Q. I have a quasi-business lunch coming up and am not sure what to wear. It is a meeting of former employees with our former employer (our company was bought out) at his house. I’m tempted to wear a suit, as it is what I am most comfortable in, but it is also likely that I will be the only one wearing anything other than a polo shirt. What do you suggest?

 
















A.  Your question reminded me of a conversation I had some time back with TV host and former Super Bowl Champion Michael Strahan. At the time, the 6 foot, 5 inch, 255-pound NY Giants star was chosen as the Rochester Big & Tall/PLAYERS INC "Man of Style," and he had these enlightening comments.

"When we are invited to an event, the other guys ask, 'Where is it going to be?'  I ask, 'What is the dress code?' If the answer is 'casual,' I ask, 'Nice casual? Dressy casual? Or blue jean casual?'" 

I commented to him that while women are accustomed to asking questions about what to wear, men are generally uncomfortable doing so, as I imagine might be your concern with your upcoming lunch. Michael seemed surprised and volunteered, "I'm big on that. I want to know what people will be wearing, then I know I will be comfortable when I am there." How intelligent and how refreshing! It is a two-second question that can assure you a full afternoon of comfort, and can often be a nice icebreaker for a one-to-one call before you attend an event where his time will be limited.  

After you’ve asked about the dress code, it is important to know what the answer means. Even for a man who prefers to wear suits, a navy blue suit, white shirt, and tie would be inappropriate -- it is far too dressy -- for casual events. In certain situations, “dressy casual" may include a suit, perhaps even a black one -- the choice of many of today's most fashionable dressers; but to soften the stuffiness of establishment dressing, it might be matched up with a patterned shirt (maybe a small gingham check) and a simple tie. Nevertheless, at your lunch in someone’s home, the black suit would quite likely be too dark and clubby looking. Something lighter would be better. In fact, a while back Michael appeared on TV, perfectly decked out in an impeccably cut tan tweed single-breasted suit (with double vents and a dressed-down attitude). I noticed that his winning daytime dressy-casual effect included an open-at-the-neck dress shirt in subtle light-colored stripes, one of which nicely repeated the tan color of the suit.   
    
Another way to go, for a step down in formality from a suit (with or without a tie), is to choose a sport coat. As an example, a brown-and-blue tweed sport coat, khaki pants, and blue shirt would make another "nice casual" combination. Matching brown shoes and brown belt would complete the look. 

Often, when the invitation suggests "casual" in any of its forms, rather than either a suit or sport coat, a man feels at ease wearing a smart sweater and/or sport shirt, no tie, and well-tailored dress pants. If you should choose blue jeans, they should be a dark wash and very well cut.

All of that said, you do have to dress in your own style, something that you are comfortable wearing, whether it is reminding others of who you are or showing the complexities of an All-Pro defensive end. Michael said to me "I choose to wear suits almost all the time. We are in business; we should look like businessmen. I have a closet full of suits. It helps to look good; then you feel good. When you look and feel good, you play good. Based on the way you dress, you can go into every situation in control."

He also pointed out that everyone is different. The distinctions he made about varying players’ personalities were fascinating: "Different positions dress differently. The best-dressed players are really the bigger guys. I have noticed that the 

• DEFENSIVE LINEMEN dress in sharp suits, more traditionally.
• LINE BACKERS dress flashier. They wear a lot of Versace and alligator shoes.
• DEFENSIVE BACKS are the smaller, cockier guys. They tend to dress over-the-top; they wear a lot of purple and yellow.
• OFFENSIVE LINEMEN are the biggest, calmest, most laid-back guys. Most of them never ever wore a suit. So they might wear olive pants and a sport coat -- as casual as you can get and still be 'dressed.'"

Michael laughed and added: "You learn! I used to have a purple suit myself. You've got to figure out what works, looks good, and says good things about you." It's apparent that today his sophistication and savoir-faire would never include a purple suit.

In your case, if you have never changed from wearing suits (that is, non-purple suits), then you need not change now. I always believed that a guest shows a very nice respect and deference to his host even if he's not a former boss by dressing up a bit. If wearing a suit is a style you are comfortable with, then it doesn’t matter whether others come underdressed or not.

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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