The “I Don’t Care What Anyone Thinks” Fallacy

I sometimes hear or come across pieces of advice regarding clothes or dressing which I then feel compelled to address.

As a dad who is trying to dress, for lack of a more specific term, better, you may feel a twinge of discomfort in those moments when you consciously try to “step-up”. These moments may look like putting on a sport coat instead of a hoodie. Or loafers instead of sneakers. Or chinos instead of jeans. You think about the environment or scenario into which you’ll be entering and realize that the other men probably won’t have made similar upgrades to their presentation, be it a school function, or church, or a gathering of extended family. That’s the origin of that twinge of discomfort. You want to look nice but you don’t want to make anyone else feel uncomfortable. You don’t want people thinking “What’s that guy’s deal? Why is he so dressed up?” You like the idea of dressing better, but you naturally want to fit in.

Here is where you will find other menswear commentators (is that a thing?) say how you should wear whatever you want, other people be damned. They can look like slobs but we shouldn’t sink down to their level to make THEM feel better. They crow, “I wear whatever I want. I don’t dress for anyone but myself. I don’t care what anyone thinks.”


Everyone cares what other people think. That’s normal. Only sociopaths and narcissists don’t. The people who say “I Don’t Care What Anyone Thinks” want other people to think that they are people who don’t care what anyone thinks.

Clothes are a language and truly elegant dressers understand that language. It’s not wrong to want to fit in with those around you. It’s not wrong to want other people to feel at ease around you. You COULD wear your white tie and tails to a backyard BBQ, but you’ll look like a screwball, even if it’s the nicest suit in the world. The, either conscious or subconscious, reaction you want your clothing choices to have is simply “He looks nice”, not “Wow, what a dandy!”

The concept of dressing well is often times a question of dressing CONSIDERATELY. It’s understanding whom you will be around and the nature of the event or gathering. Taking these things into consideration isn’t an act of timidity. It’s not watering down your sense of style in the face of perceived peer pressure. It’s having an appropriate level of emotional intelligence.

For the record, that’s a good thing.

Here is an example of a time when I was not as considerate as I could have been when it came to how I was dressed…

Years ago, before the kids were born, my wife and I went out to dinner every Saturday night. The best restaurant in town was less than a mile from where we lived which meant we didn’t have to drive and could imbibe with impunity. We became “regulars”, as you would say, and our champagne was always ready at our table as soon as we sat down each evening. The restaurant was upscale and my wife and I reveled in the opportunity to dress up (my wife said that whenever we walked to dinner we looked like Batman’s parents).

One weekend we planned on having dinner with another couple, two very close friends of ours. For reasons I cannot recall the wife ended up being unavailable that evening so my wife and I went out with just the husband. Instead of our usual restaurant, the three of us chose another spot in town. The vibe of this place was a bit more casual in a rustic wine bar kind of way. Still very nice, however.

Since my wife and I just like to dress up and this was Saturday night, I wore a jacket and tie as I always did and she wore a dress and heels. Our friend wore a polo shirt, khaki shorts, and sneakers.

Here’s the thing: None of us were inappropriately dressed for the setting. Granted, we were on either ends of the “appropriate” spectrum but no one batted an eye when we all walked through the door. What I am getting at is that there was no “right” or “wrong” way to be dressed in the scenario. However, we did feel a little uncomfortable at first. He had an “Oh crap, I forgot they like to dress up for dinner” reaction and we had an “Oh crap, we forgot that not everyone dresses like this for dinner” reaction. But then we all had a few cocktails and everything was fine.

No one was at fault. No one was dressed sloppily. Everyone looked very nice. But there was a silent dialog happening between us because of what were all wearing. I felt a little uneasy because I had neglected to consider that my good friend likely would be dressed more casually. He felt a little uneasy because he neglected to consider that he was going out with us and he knows we always dress up for dinner. I felt a little overdressed. He felt a little underdressed. I wanted him to enjoy his evening and he wanted the same for us. Because we are friends. And that’s normal.

Was I being a little too sensitive? Possibly. Maybe he didn’t notice at all the differences in what we were all wearing! I could have just said to myself, “Whatever, I don’t care what anyone thinks. I will wear what I want”. But the truth is, I DO care what other people think, especially my friends. Again, that is ok.

Are these “I Don’t Care What Anyone Thinks” people so rigid that they can’t dress down sometimes? If there was a gathering and everyone was wearing a suit, these people would say “Well, you should also wear a suit so as not to selfishly draw attention to yourself. You should respect everyone else and dress on par with them.”

However, when the pendulum swings the other way and the gathering is more casual, these same people put on their spats and trot out the “I don’t give a damn” line.

Why the double standard? Are the people who dress more casually somehow not worthy of that same respect and consideration for their feelings?

Sport coat or hoodie? Loafers or sneakers? Chinos or jeans? As you get more practice and hone your true style you will develop an ability to spot those nuances and adjust accordingly.

It is that consideration of others that will make you a stylish and elegant dresser.

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