Behind the perfection of a man's style, must lie the passion of a man's soul.
Oscar Wilde
My dad has always been a natty dresser. Even now in assisted living, he insists that the color of his pants and shirt be compatible. He never appears for meals two days in a row wearing the same thing, and is appalled at the prospect.
Coming up, I got to see my father wearing all sorts of weird but fashionable (then) items. If you don’t know what a dickey turtleneck is, look it up and be prepared to guffaw. Ah, the seventies.
Lest you think my dad was an executive or a salesman or some other sort of white collar worker, let me disabuse you. He ran printing presses for newspapers and magazines in Philadelphia and was blue collar and union. His sartorial tastes, though, were influenced by his dad, Louis, née Lucio, an Italian immigrant and master tailor who always dressed impeccably in a handmade three-piece suit as he imperiously took his evening stroll through the Overbrook neighborhood of West Philly. The kids in the neighborhood, my dad’s friends, called him King Louie.1
So it was only natural that I continue the tradition. Still, when I was an English professor, I admit that I too donned the shabby-chic uniform of my tribe: tee-shirt, jeans, Converse All-Star high tops (black), and a sport coat. Always a sport coat. In fact, I wore sport coats the way other people wear windbreakers. I wore them on camping trips. Eat my s’more, King Louie!
When I became a college dean, my wife took me shopping so I could look the part. I bought a bunch of suits and other professional attire, and every day I wore a suit to work. Like my grandfather, King Louie, I was impeccable. My tie would stay on until I got home and sometimes long after if we went out. Even on casual Fridays, I would relax only enough to wear separates — dress pants, dress shirt, sport coat, and dress shoes. My only other conciliation would be that my tie might, might feature the school colors if they matched what I was wearing.
Given my longstanding philosophy that leaders should be open and approachable, particularly when they are bosses, it may perplex some of you who did not know me then to learn that I was so formal in my dress. In fact, I have a closet full of French cuff shirts, which have moldered in the Covid era. So, why was I so well-tailored? Wouldn’t my suit-and-tie put off the scruffy professors who reported to me?
To be honest, much of the reason I wore suits every day was just personal inclination. I liked to play dress up. You have to understand that I look real good in a suit — that according to the only person whose opinion matters, my lovely and horribly myopic wife. Oh, and did I mention that I also have a taste for fedoras, which only, um, tops off, my predilection for leather jackets? Yup, there I was bounding across campus in a cool leather jacket, snazzy fedora, and flashy business suit.
Keen.
At the same time, there was some strategy involved. The suits were meant to send a signal — that I stood apart, that I was not entirely one with the faculty and administrators who worked under me.
Surprised?
Let me explain. By dressing with intent, I anticipated, in a material way, what John Amaechi recently advocated in his excellent book The Promises of Giants: “be bold and vulnerable.” That is, I was consciously putting myself out there visually as “the boss” while, also consciously, not behaving like a typical boss as much as possible. I got better at managing this dichotomy over the years ironically as my bossing titles grew more boss (if you catch my drift). In other words, I was less bossy as I became more of a boss even though my clothes grew bossier still. Oh, and one of my suits was by Hugo Boss. And would elicit cries of “You go, boss!”
In my imagination.
When I first became a dean, I was advised to leave all my faculty ways and mindsets behind. Leaders, I was told, stand entirely apart from their people. I could no longer think of such unwashed folk as friends and colleagues, which really went against my inclination. For many months, though, I complied with this advice by assuming the role of the boss that matched the suits. Eventually, though, I realized that I was miserable and ineffective while playing that part. I thought, what if there were another way? I was no longer faculty, but I also was not entirely comfortable with the role of boss-apart, the manager who did not fraternize with the little people. I embarked on an adventurous experiment.
I resolved that, against all advice and the example of my superiors, I would loudly project boss through all the superficial means — clothes, office, desk accessories, etc. — but my actions would be more those of a real person. And there is a difference between a boss and a real person. To be clear, I also learned to eschew playing the fool and pretending to be “down with the people.” When you are the boss, that stance is both false and insulting. Instead, I just tried to act decently with people and to project some reasonable facade of being a human being despite my title, my posh pen and pencil set, and my collection of luxury paperweights. I would be ever-conscious of my role and my need to lead, but I would also be myself as much as allowable.
Of course, this was a trial-and-error activity as well as being fluidly situational. I got it wrong one way or the other all the time as I tried to recalibrate for this person and this group and this circumstance all while managing my own moods, needs, and ego. As difficult as it could be, though, I found I grew much more comfortable with myself and confident in my leadership role. My suits expressed my bosshood, but I expressed me from within them.
I also noticed that most people began responding to me in more positive ways, as though I were approachable and even (heaven forfend!) trustworthy and deserving of respect. Let me tell you. When you are the boss, not playing the role of boss is hard because everyone, and I mean everyone — your employees, your peers, and even your own bosses — expects and demands it. Still, the more I shed that role, the more my people and others looked to me for leadership. As my perceptions and mindset changed, so did theirs. Sure, some jerks saw me as weak and tried to take advantage, but I was secure in my suits, which could also serve as a sort of armor when necessary.
Now, I am aware that these sartorial details play out very differently for women. Still, I think the basics are there: expressing a message of authority with your attire while behaving in a way that befits your status as a decent human being. I would love to hear from women if they agree or not.
The way I figured it, if I could pull off wearing a fedora with a leather jacket and business suit, I could pull off dressing like a boss and acting like a person. My results varied, but I like to think that the combination worked more often than it failed. I can attest that my mildly eccentric approach was disruptive in a way that was healthy for the stuffy, status-quo oriented culture of universities. I can also say dressing with intent took some fortitude and a great deal of attentiveness.
So where do I go from here? I think my next sartorial move should involve capes or maybe a dapper dickie.
Do you consider the messages you send through your appearance and through your behavior? Whether or not you are a boss or leader, do you dress with intent?
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I recently learned from my father of another King Louie story. Apparently, my paternal grandfather made two tuxes for himself — a summer tux and a winter tux. He did this so that he would be properly attired for burial depending on the time of year. My dad added with a chuckle, “he died in October.”
On Suits