The ‘20’s: Dressing the Modern Man

I don’t know when men turned the tide of taking functional dress so far that we learned to champion looking as not good as possible. I hear it all the time.

“Men just want to be comfortable.” Fair enough.

“Men don’t care what people think of them.” Yes, they do.

”It isn’t manly to spend too much time on what you look like.” The hell it isn’t. Though,  fallacious declaration of masculinity aside, I agree that donning appropriate attire should not be an arduous task.

But first, lets address the dapper elephant in the room: We absolutely care what we look like. The man that works in construction that uses their worn and weathered work gear as a testament to their uncaring would likely be staunchly opposed to showing up in a dress. He might not care within the choices he’s kept available, but there is some threshold of importance placed on appearance. He doesn’t consider that dresses and similar garments have been worn by men during many different time periods. Appearance has mattered to men since long before high heels invented for knights on horseback predated work boots as the ultimate mark of masculine footwear (the higher the heel, the more valiant the knight. An early proclamation of “mine is bigger”). The blue collar worker may not care that there are layers of soot imbedded into their jeans, but they care enough to make sure they are dressed appropriately for their vocation. We also see this in corporate settings. A man may claim he doesn’t care that his collar is wrinkled because he does not want to appear to care too much. The same man paradoxically cares enough about his appearance to ensure that he looks like he doesn’t care. It should also be of grave concern to everyone around him that he went to such lengths just to make himself look blatantly contemptuous. Our clothing is a costume of sorts.  It works to turn us into a symbol to others. We signify what context we are showing up to and what role we showed up to play. The end process of signifying is, literally, to grant significance. It tells others how to categorize us, as others naturally do at first glance. It isn’t wrong for others to gauge their initial interaction with someone based on what they see. One might ask if this means we should allow ourselves to be affected by the opinions of others. This question, however, misses the point. You can’t control people’s opinions of you, but you can influence their perception of you. So instead of asking why you should care what others think, ask yourself: How seriously do you want people to take you?

It is easy to stop at this point and think that people shouldn’t be judgmental and should get to know someone before evaluating them. I agree with this assertion. I am not talking about what people should do. I am conveying the importance of understanding what they actually do. Our propensity to make snap judgments based on appearances is a matter of evolutionary biology, not a flaw of common personality. These systems we use to categorize originally helped us gauge threats in primitive environments. In a civilized world, they do a more thorough version of the same thing. Imagine you are out at a mall and someone is walking around casually in a bulletproof vest. Are you automatically going to assume they’re just expressing themselves through style, or are you going to wonder why they’re overwhelmingly prepared for a shootout? Our clothing aims to prepare us for the context we’re entering. This includes protecting ourselves socially. Dressing appropriately for the environments we choose to enter signals safety to others. Among passing strangers, we cannot know the others’ intentions. We can properly associate their attire with adherence to the immediate social standard. This social standard can be synonymous with standards of personal safety. Consider the stereotype of wearing a-shirts (you’re not still calling them wife-beaters, are you?) to a street fight. This isn’t inappropriate attire at a casual restaurant because people are plainly judgmental. It is a stark departure from casual expectations and commonly associated with blatantly unsafe environments. We don’t just dress for occasions, we become active participants in different environments. This is the case of most modes of dress. It is not a matter of dressing, but a matter of becoming. This is hardly limited to dress codes in high-end restaurants. Consider Halloween and how we playfully act out the character we’ve dressed as. I have spent many late Octobers dressed as Derek Jeter, adorned in Yankee pinstripes and perfectly mimicking his upright batting stance upon request. Someone in a Popeye costume would mimic his trademark laugh and someone dressed as a vampire might pretend to be afraid of garlic. While Halloween is a playful pursuit, the practice is merely a parody of our day-to-day. We play our role the best we can within our respective context. We should present ourselves each day as competent and capable men. When it comes to “who we are” in the most basic sense, “who we are” is contingent upon the role we play within the context we arrive to. Our attire symbolizes why we’ve arrived to the place we’ve arrived to. The difference between green fatigues and red armbands in World War II was life and death. This doesn’t mean we should always dress for war. This is to illustrate that the symbolism we choose to display on our person can be that powerful.

Why does this make it important to look your best? When you dress to show that others can expect your best, and can meet those expectations, the surrounding world is enhanced as a result of your positive contribution from the moment of arrival. Many automatically consider this to be dressed in a suit and tie. While I maintain that even in today’s modern age, a grown man should have at least one good suit, that has nothing to do with dressing your best. It’s easy to spot the man that tried too hard. They don’t look like themselves, but rather a mannequin for their outfit. The clothes should highlight the best facets the man brings into a room. The best dressed man on a construction site has the necessary tools on his person to do the job. The best dressed man in a firefight has extra ammo at the ready and a tourniquet easily accessible. The best dressed man in the boardroom has his clothing in good repair, and a notepad and pen in front of him. In all of these examples, the best dressed man is also comfortable. Notice, that best dressed does not necessarily mean wearing the finest clothes, but is prepared to give their best within their context. An outfit works because it properly conveys the best a man brings to the table, not because it festoons him with gaudy distractions. An example of this is the guy that shows up for a pickup game of basketball decked out in wristbands, shooting sleeves, matching sets of gear and expensive Jordans, but can’t handle the basketball for more than a few dribbles before having it stolen.

The larger point of looking your best is understanding that you mean something to the world. You’re significant in the most existential sense. Think of appearance as a conceptual practice. What does someone inherently associate your appearance with? Is it with good character and competence? Wisdom and intelligence? Drive and conscientiousness? Kindness and good humor? Wherever you go you are a participant within the areas you play a role in. Some men shun the idea of dress codes, positing that it shouldn’t matter what they wear. They treat the environment they enter as if it should be presented to them as a spectator rather than understanding themselves as an active participant. But just as the furniture makes the room and the placement makes the space, the people that fill the room compose the score. Each and every person that enters the room, permanently changes the room for every person that enters after them. Right down to the room temperature and volume, even the shy person is important to the collective functioning of the environment. On the worst of days, you can still add something just by showing up. If all the energy you have can be spent on showing up in the best way you can, your presence itself can be meaningful. Your attendance alone can absorb the legwork needed to convince those around you that you are worth their time and attention. This might sound like a brutal transaction. But the intrinsic question remains; when someone sees you for the first time, what do you signify, represent, and symbolize to them?