Q. My friend and I argue over the concept of "If you know the rules you can break them." When he wears a button-down-collar shirt without a tie, he does not button the collar because, well, I don't know why, something like the collar is for ties and otherwise he should go for a '70s disco look. I imagine you can wear white before Memorial Day, but otherwise rules like this have a reason. Please tell him I'm right.
A. Wow! A question to warm my heart. I'm with you on this one. What-to-wear rules do have a reason, and usually it is that they make dressing simpler by eliminating a lot of uncertainty.
Of course, not all rules are etched in stone and not every rule must be obeyed to the letter. But some rules -- those that come under the heading of "never" -- are helpful. They keep us from being uncomfortable.
Here are a few of my "never" rules for men to follow:
Never wear a necktie with a sport shirt that has two pockets.
Never wear a tie with a short-sleeved shirt (there is no such thing as a "short-sleeved dress shirt").
Never leave a space between the bottom of your tie and the top of your trousers.
Never wear socks with sandals.
Never wear dark socks with white sneakers.
Never wear all-white leather dress shoes.
Never wear matching white shoes and belt.
Never wear an exactly-matched set of necktie and pocket handkerchief.
Never wear more than two noticeably eye-catching items at the same time.
Never wear a belt with black-tie attire.
Never have cuffs put on formal trousers for black-tie wear.
And, yes, never leave those two little buttons unfastened on a button-down-collar shirt (with a lot of button-downs, the collar is supposed to have a soft "roll" which, without the buttoning, may fly up or be too-crisply ironed down).
Many of the dozens of other dress rules allow for some interpretation, but keep in mind my overall advice: First, know the rules; then you can break them. You may on occasion see a truly well-dressed man wearing something that does not seem quite right. But when you do, it is usually done on purpose and done artfully. An example is David Letterman's habit of wearing white socks with his dark dress suits. This is a purposeful quirk ("mistake") that only works because everything else he has on is quietly tasteful ... and because he is in the professions of entertainment and amusement.
Offbeat, on-purpose incorrectness in men's dressing is known as "sprezzatura." It's a sophisticated Italian word for a rather sophisticated concept meaning "artful dishevelment," and sometimes described as "making the difficult look easy." The best-known example of this style of dressing was practiced by Gianni Agnelli -- son of and heir to the Fiat auto family fortune. He was the richest man in modern Italian history and often described as "a cad, an entrepreneur, and a legendary fashion icon." Famous for his quirky, but elegant, style of dressing, he was widely known for wearing his wrist watch over the cuff of his shirt to convey sprezzatura. Such studied nonchalance may sound goofy, but because everything else he wore was so impeccably correct, it all worked.
If you, or your friend, are so self-assured that some small offbeat ways of projecting your individuality and style will not come off as mere ignorance of the rules, I give you my blessing. But be prepared to come under some intense scrutiny. Remember that people you meet for the first time don't know you are intentionally breaking the rules.
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High Profile on 07/06/2014