You can always tell whether you are at a hacker con or a corporate-oriented conference in our business. The hacker cons have plenty of tattoos, piercings, fringe hairstyles, and the like. In fact, I’m usually more concerned that folks will think I’m a narc because I have none of the above. But this brings me around to the idea of appearance and its impact on your career.

I think Lee and Mike had a good, reasoned response in their Fashion Advice from Infosecleaders post. The question is about a guy, who is climbing the corporate ladder and now finds himself having to dress the part. And it’s uncomfortable. Lee and Mike’s general thought is that he needs to deal with it, and that to play the game you have to look like you are in the game.

And maybe they are right. But they might also be wrong. I think there could be other factors at work here, based on experiences I’ve had, because I’ve very rarely looked the part in any job I’ve had.

Let’s start with my early META Group experience. I was in my early 20s and looked 18. My hair hadn’t started turning gray yet, and I was sitting across from CEOs and folks whose networking budgets had 9 or 10 zeros. I would be brought in to discuss trends in networking and telecommunications. The reality was that some of these networking jockeys probably had underwear older than me.

So as you can imagine the first few minutes of each meeting were always pretty interesting, as everyone in the room sized each other up. I was far less snarky at that point so I usually didn’t antagonize the clients with tales of beer funnels, pet rocks, and dances with girls. You know, the stuff us kids used to do for fun in the olden days. Most of them took me for a lightweight and thankfully they didn’t have BlackBerrys back then, because I imagine they would have started banging through email before the introductions ended.

But then a strange thing happened. Pretty much every time. I started talking. I answered their questions. I provided perspectives on trends that indicated I actually knew what I was talking about. Who knew? This young whippersnapper actually talked to lots of folks and although a front-end processor was invented while he was still crapping in diapers, he understood IBM’s product strategy and what that meant to these poor saps who had to make the stuff work.

I actually kind of enjoyed that expectations were pretty low when I entered the room. It made impressing clients much easier.

Now back to the topic of attire. Truthfully, I’m not sure whether this guy’s problem is attire or self-esteem. You see, he feels different, and therefore the senior team treats him as different. He doesn’t seem to believe he belongs at the table with the big boys. So, I believe, senior folks pick up on that and realize his self-fulfilling prophecy.

If you don’t think you belong in the club, you are right. If you have confidence in your abilities, know you speak knowledgeably, and are not intimidated by muckety-mucks who believe you need to wear a tie to be successful, you should be fine. Even in your khakis and button-down shirt. And if your organization truly judges you based on what you wear, and not what you know and what you do, then you are working for the wrong organization.