How To Deal With Judgmental People

I sat down to write this article thinking it would be one of those pieces that was “easy” to write. I thought the words would flow pretty effortlessly, as they often do, with a topic that I’ve thought about endlessly since I began my own sartorial journey so many years ago.

But the words didn’t come easily.

As I sat in front of my blank Word document, I realized that this was a much larger, thornier issue than I initially thought. Because dealing with judgmental people is often the most difficult aspect of getting dressed, no matter what your style is.

Look, we all have a natural desire to “fit in”. That’s just evolution. Fitting in with a group ensured our individual survival. If you did something to make the wider group question you or become suspicious of you, you risked being ostracized. That could mean the death of personal or professional relationships, which meant your livelihood and personal happiness could be threatened.

Talk about a lot to consider!

But what if, even given your desire to be accepted by your social sphere, you wanted to step outside a particular comfort zone… in this case, your wardrobe? How do you do that without incurring the judgement that naturally accompanies the alteration of something as fundamentally and immediately communicative as your clothing?

Clothes have always sent powerful signals to those around us. Changing any aspect of how we dress will be immediately noticed and judged.

And that’s what usually halts well-meaning guys from taking meaningful steps in their personal presentation. They’re afraid they’ll be made fun of. They’re afraid people will go “Oh, so you think you’re better than me now?”

And those fears are valid!

The question here, though, when deciding to change how one dresses, is not “How do I avoid being judged by others?” but “How do I deal with the judgment of others?”

Because you WILL be judged. There’s no getting around that. If you change up how you dress there will be people who change their opinions of you.

And that can be scary! I don’t know of anyone who WANTS that kind of attention. Often we just want to wear what we like and get on with our lives! We’re not looking to make a splash or start any conversations about it.

But those people are always there, ready to throw out a sarcastic comment intended to make you feel just a little sh*tty about yourself.

I’ve been there, trust me. When I first started getting into menswear, I wanted people to start thinking of me as responsible and capable. Basically, I was tired of being viewed as a child. I wanted to take a meaningful step into adulthood. At that time I was about to get married and was progressing steadily in my career. I wanted to put distance between the person I felt like I was at that time and the kid I felt like I was before who wore hoodies and sneakers to the office who people sometimes mistook for a high schooler.

Unfortunately, in those early stages, I was surrounded by people who felt very uncomfortable seeing someone make improvements in their style. For a long time, I felt very uneasy about that. I felt like I was doing something wrong.

Now, it wasn’t like I was wearing tuxedos everywhere I went. I was making small upgrades to my style, like wearing a blazer to the office or a jacket-and-tie when out to dinner with my wife. But those small style adjustments were seen as threatening by many of the people in my social/professional circle.

So, how did I overcome it? Well, I kept a handful of things in mind. Here they are…

First, know that it’s ok to be intentional. I wrote an article about this a long time ago. Sometimes, we get embarrassed when we know that other people know we are trying. Because trying means possibly failing. If you never try then you can never fail. That’s safe, sure. But it’s not going to help you dress better. If you’re too timid to try, then you’ll never get enough practice to develop the necessary skills for dressing well. That means you’ll just wallow around in mediocrity and insecurity forever.

Not exactly my idea of fun.

Remember, people who judge you negatively for trying to dress better are trying to bring you down because THEY feel insecure about themselves. They are often fearful and react viscerally to anything that isn’t familiar. Are those people all that important to you? Don’t let them dim your light.

Because at the end of the day, who matters most to you… the people who will appreciate and support you in your style journey, like your wife?… or your stupid coworkers/acquaintances who spend all their time playing video games and complaining about their spouses?

Are those people really going to matter to you in five years? How about two years?

The people who really matter will either support you or won’t care all that much. They certainly aren’t going to judge you.

There is a bit of skill needed in going about changing up your style, however (which you already knew). You have to be “good natured” about it. If you’re dressing better because you genuinely think you’re better than other people… then you probably deserve to be judged harshly. But if you’re honestly just trying to present your best self to the world, you shouldn’t feel self-conscious for that.

There also needs to be some level of authenticity in your journey. I have written about this before, too. Your job, your hobbies, where you live, are all things that add to, or detract from, the authenticity of how you dress. If you’re stepping out in your top hat, white tie, and tails every day, regardless of what you’re doing… then I wouldn’t blame others for casting a bit of a side-eye in your direction.

You can dress “up” or dress “better” and still be perfectly appropriate for your day. Some people might wear jeans to the office, but if you wear chinos and a jacket, you’re not being “inauthentic” because what you’re wearing is logical for your activity, even if it’s a few levels above what everyone else has on.

Unfortunately, it needs to be said that, you sometimes might just not fit in within a certain place. That happens.

In cases like those, you’ll always be viewed as the outcast. You’ll never be trusted. You’ll always be viewed superficially. In those instances, you can either opt to blend in and be accepted (and give up on your sartorial journey) or continue to dress the way you like and stand out.

If you decide to continue to dress the way you like and stand out, you either have to perpetually deal with the judgements of those around you, or you can get the heck outta Dodge and go somewhere that more aligns with your personality.

That’s ok.

If, for example, you want to wear 3-piece suits and pocket watches all the time, you might not ever feel comfortable living in a very rural area. You might just naturally fit in better in a city where that style of dressing is more widely accepted. Similarly, if you gravitate to heavy boots and cowboy hats, living in a city might not make you feel comfortable in the long term.

Clothing is a language, obviously. And there are times when people misunderstand what we are trying to say with our clothes. We might think we’re saying “I am responsible”, but those people misinterpret that as “I am better than you and I can’t be trusted”.

But don’t concern yourself with the people who can’t speak your language.

Because the people who matter understand the language perfectly.