Put This On reader Matt Grossi just sent this to us, and I thought I’d go ahead and share it. – Jesse

Why I (Finally) Care (a Little) about my Clothes



I do not have a winning record in the game of dressing myself. In high-school, my wardrobe consisted entirely of professional wrestling and comic book t-shirts. In college, I wore the same two polo shirts (at once, on purpose) every day for three years, which eventually led one of my professors to ask me, quite sincerely, if I was okay. After getting my first job, I walked out of a discount menswear store with an armful of pleated zoot suits so horrible that even my boss, who wore black jeans and twenty-year-old sneakers to work, thought I looked bad.

I got this way on auto-pilot. I never really put any thought into the way I looked, mainly because I figured that my looks were the last thing on earth that could possibly matter. College-me, had he been asked, would have defended his slob-hood on the grounds that content matters—presentation and appearances do not.

Isn’t it true, college-me would go on, that the Mona Lisa would be just as great, even if it were set in a two-dollar frame and hung in some attic? The content would be the same. The soul of the thing would be the same. It makes no difference how a thing is adorned or presented. And doesn’t this same idea go for people and how they dress?

Many men my age (twenty-seven) would probably agree without thinking—how someone dresses is a trifle compared to the character and content of that person. This weird idea of a winner-take-all contest between content and presentation is one major reason why so many young men dress the same way as adults as they did in the sixth grade.

For me, this idea started to crack when I accidentally put on clothes that actually fit and looked great. The particulars make for a long story, but the essential part is that I put on the right clothes and suddenly felt invigorated—and I chased that feeling.

Eventually, I concluded three things:

(1) Just because the content of a thing (or person) is what matters most doesn’t mean the presentation of that thing (or that person) doesn’t matter at all.

Consider the business report. The figures and analysis are the content—the soul and purpose—of the report. But a shoddy design will render the content incoherent and impenetrable. If you have ever tried to decipher a poorly designed report, you know that presentation counts for something.

Similarly, as a human being, I ultimately want to be judged by my character and my actions. Indeed, one would have to be two parts snob and twenty parts psychopath to declare, “judge me by my dress, not by my deeds!” But my clothes and my character aren’t competing values between which I must only pick one.

(2) My clothes, just like my mother always told me, send signals about me to others.

Your mother or your guidance counselor probably gave you the same lecture, and maybe like me, you ignored it, figuring that only shallow people notice your clothes. If so, you have been a fool, because everyone notices, whether they mean to or not.

Imagine that you see someone walking down the street in a potato sack—you couldn’t help but notice this person’s “clothes”. And this choice in clothing certainly sends a message—something along the lines of, “I spent everything I had on scratch-off lottery tickets…then I stole this potato sack out of a dog house…please help me.”

Or imagine you’re at lunch and you see a man at another table dressed in black leather pants, black cowboy boots, a tattoo parlor t-shirt, and a bandana holding back his very long hair. There is an above-average chance that this man is either (A) a biker, or, (B) the drummer for Shinedown.

(By the way, unless you are actually the drummer for Shinedown, or Lemmy from Motorhead, or in some other way professionally obligated to wear black leather everything, you probably belong in regular clothes).

And any time you see a man in a suit, you can very quickly place that man in one of two categories. The first category is for the man who looks relaxed and natural in his suit—his message is, “I am a serious man who is doing something I care about or going somewhere important.” The other category is for the man who looks uncomfortable or buckled into his suit, like it is the first time he has worn one in years—his message is, “my mom made me wear this.”

The point is that everyone judges, quickly and automatically, others based on how they look. Not just shallow people, and not just jerks—everyone. You can go on not caring, and continue to wear mesh shorts to important occasions, but you can’t go on pretending that others don’t notice.

(3) The most important point: the clothes I wear send signals to me about me.

The real clincher for me—the thing that ultimately transformed me from utter slob to someone who somewhat gives a crap—was when I realized how much better I felt when I wore the right clothes.

When I change out of my pajamas, for example, and put on real clothes, I am telling myself (and the world—see point number two) that I expect to engage in activities more challenging than laying in bed. I could tell myself all day that I am very serious about my business, whether I wear pajamas or something nicer, but by actually wearing something nicer, I’ve taken a concrete action towards demonstrating this seriousness. My clothes are a clear signal of what I expect from myself.

Consequently, if you catch me wearing Under Armour and combat boots, you’ll know that I expect to be auditioning for a role in Stallone’s next movie.

To be clear, I am arguing for dressing well and not for dandyism. A man dresses well when he looks great in clothes that are in line with his aims. A man is a dandy (or metrosexual, or fop, choose your word) when his clothes are themselves the aim. If you ever find yourself more interested in your clothes than your actual pursuits, consider becoming a tailor and making it official.

Whatever holds a man back from dressing well—auto-pilot slob-hood, or the idea that good clothes are always expensive, or the prospect of spending the time to learn a little, or fear of being thought a silly dandy—will disappear once he realizes how much better he looks, and consequently feels, in clothes that fit and suit him.