How to make your footwear a style shoe-in

Q. I read your article about shoe colors and would like to know if you will comment about tennis shoes and dress? In my city there is a well-known TV newsman who wears tennis shoes, even with a tuxedo, at events where he is the MC. He is very popular, and I can’t remember ever seeing him dressed otherwise. Thank you.

A. The key words that apply in your question and that affect my answer are “well-known TV newsman” and “popular.” The person you are asking about is a celebrity. This gives him a vast range of rules that may be broken and allowable mistakes. Celebrity has its privileges. Your TV newsman example is using his celebrity advantage, which allows for attention-grabbing and self-promoting eccentricities. How popular he is and how famous he is define how well his rule-breaking is accepted by the public.

As I have said before, some sartorial mistakes, when committed by the average man, come off quite clearly as clueless errors. As an example, when you see the bus driver wearing white socks with his dark uniform pants, it is just wrong. On the other hand (or foot), when we used to see David Letterman, meticulously (and knowingly) perfectly dressed in a well-tailored Paul Stuart suit, black shoes, and white socks, we knew it was his signature statement: he was inviting the world to notice his unusual choice, even though he knew full well that it was not correct. The length of President Trump’s tie is another example.

The same was famously true of Ralph Lauren when, early in his career as a men’s style guru, he wore a rather affected black-tie combination: a perfect tuxedo with all its accepted accessories except for one: instead of the requisite matching black trousers with a silk ribbon down the side, he wore blue jeans. Everyone knew it was technically all wrong, but who would think for one moment that Ralph Lauren did not know any better? No one. Those who saw a picture of him dressed that way thought, “How clever of him to switch things around so unexpectedly.” Not many men thought to themselves, “I think I, too, can pull that off.” They also didn’t have a jeans line to promote.

Most of the rest of us mortals feel our best when we follow the correct “rules” of dressing well. By following the norm, men are certain that they are not straying too far; and they can be assured that others are not questioning either their knowledge of the rules or the extent of their non-conformity. Typically, many men don’t want to stand out too much, at least in these terms. By contrast, some men like to play the role of the maverick; they want to be noticed and enjoy making a statement of individuality with what they wear. I believe most men are somewhere between these two: while they may not want to fade into the woodwork, they definitely don’t want to be thought of as a “look-at-me” type of guy.They may admire the man whose appearance calls attention to itself, but they don’t want to be that man.

The world of dressing well offers men an array of possible ways to stand out just a bit and separate themselves from the crowd. Here are a few special touches that I have noticed among executives. One of them might appeal to you.

• Carry a fine, imported leather briefcase.
• Enjoy the tactile pleasure of wearing a beautiful alligator belt.
• You might collect antique cuff links and wear them in your French-cuffed shirts.
• Personalize your wardrobe with color, emphasizing one or two shades in which you look your best and often get compliments.
• Instead of showing you are a rebel by not wearing a tie, be the one guy who always wears great-looking ties.
• There’s the old reliable: a colorful silk pocket square or a linen handkerchief tucked into your breast pocket.
• You may be constrained by company disapproval of deviations from “accepted” office dress. Outerwear, donned as you head for the elevators, may be the answer. Wearing a hat might be your point of distinction. How about an Irish tweed cap or a classic fedora? Or perhaps a white cashmere scarf or a long, brightly-colored muffler?

Regarding black-tie flair, there are definite options less extreme than sneakers. Particularly at this time of year, even men who almost never have an opportunity to dress in black-tie attire, may actually receive an invitation that includes the words, “black-tie preferred,” “black-tie optional,” or maybe best of all, “creative black tie.” Even if you respect timeless style, this could be your moment to try out a tweak or two. Perhaps a perfectly-hand-tied dark plaid bow tie, or black-and-white polka dot formal braces (suspenders), or handsome vintage cuff links and studs inherited from Granddad, or a contrasting double-breasted formal vest instead of a matching cummerbund, or even a small fresh flower tucked into your lapel. Any one or two of these could be a nice touch. If you work for Nike, then . . . maybe you can attend the company gala in Air Jordans.