The Appearance Myth

By Mike Rothman

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.

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Clothes are tools just as much, and as necessary, as NSLOOKUP. As such you need to know how to use them… and yes, you should still RTFM - even if there are way too many to do so and most of them are… well, in a public forum I can really say what I think of most of them.

However, you still need to understand your tools and know where to use them. You will damage any respect for you (assuming you have any) just as much wearing a suit and tie for a server build in the data center just as much as wearing your AC/DC shirt with jeans when you go to help the CEO/CIO/CTO/etc with undeleting that email in Outlook.

However, just like that ‘paper MCSE’ on the service desk that can recite every option for the PING command… just cause they have the cert doesn’t make them “one of us”. So to, just because you are wearing the suit and tie doesn’t make you “one of them”.

Remember that one guy at that conference? You know the one, the guy that just stood out like a sore thumb… you could tell he was trying to fit in… but was failing hard. Well, unless you have the self confidence that you know what you need to and can do what is asked of you.. you’ll stand out just like that guy.

So in summary (and thanks for getting to this point!): (1) you need to view clothes as a tool, one that you need to use appropriately according to the circumstances, and (2) you need to develop an appropriate self confidence. Thus armed you will be able to do your job and enjoy the situation (as much enjoyment is there to enjoy at least).


By Zac Bergart

You’ve always looked like a narc, but when Hoff started wearing long sleeved shirts,I made a visit to Brooks Brothers…

By Jack Hembrough

It’s like I told you at RSA a few years ago:  The weirder I look, the more people assume I know.

I do wear “corporate-looking” clothes, but that doesn’t stop me from painting my nails, wearing earrings, or having “fringe hairstyles” once in a while.

I don’t think it’s hurt my career at all, but then again I’m firmly convinced that I belong in a board room telling a bunch of execs how they should do things *shrug*.

By Brian Keefer

Oh man Mike, this was a relevant one. I’ve been slightly abusing my youngbuck status to be a little more opinionated, eager and gung-ho. And I guess it’s paid off. As I’m transitioning into a more leadership style role, I’m realizing the body mods will need to be covered due to the conservative culture of my employer. Queue up a trip to Banana Republic and save the v-necks and cowboy boots for the weekend. But without advertising myself as something different from the start, I’m not sure I could’ve made the jump as quickly as I did.

I’m not retiring the Converses just yet though.

By @kylecooper


Good points, but I have a couple. First, not everybody has your boundless self-confidence (fortunately?!?). Someone could have a perfectly normal (healthy) ego, but still feel intimidated. Lots of folks feel “clothes make the man”, so that prop might be useful or important.

Second, many people think dressing the part is important or essential, and this is probably disproportionally true of managers. Neither you nor I has much basis for challenging GQ’s assessment of his bosses. It’s not *necessarily* worth polishing up the resume and finding a new gig if there’s a (silly) expectation that with a promotion comes a wardrobe upgrade. And getting haircuts more often is probably a good trade for the raise. But if he feels uncomfortable or that it’s unfair, it’s time to find the next opportunity.

That said, I’m very pleased that I can get away with whatever I want to wear to my job, and it’s a significant improvement in my quality of life—nicely contrasted against my last (bank) job, which did require a new wardrobe.

By reppep

I read that same article and had similar thoughts. Really, you can’t go wrong with looking the part and fitting in with the suits. But that’s not always necessary and depends entirely on office culture and personalities.

I strongly think people should be who they are, especially when you’re beyond the point of making that first impression with anyone. Part of the whole last 15 years of work-life balancing acts has been to feel better about the hours spent at work rather than having it feel like an unhappy ball-and-chain around your neck.

It’s strange, but it’s one of the ways I look up to Hoff in a way, with his full sleeves and C-level clout. More effin’ power to ya, ya know?

By LonerVamp

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