How Dressing Dumpy is a Status Symbol

Jeff Graham

Yesterday I sold my freezer to a very rough looking guy that we’ll call Andrew. Andrew had a biker t-shirt on, dirty shorts, flip-flops and sported a long goatee. I had the distinct impression he hadn’t showered in a while, and he didn’t seem to particularly care how he looked.

Based on his appearance, I figured he must either be in a trade or do something illegal, because there was no way a guy like him could pull of a white collar office job.

“I work in IT security” he says to me, as my mouth gapes slightly in disbelief. Incredulous, I start asking him some pointed questions about IT, because surely this guy was lying to me. He proceeded to describe in great detail how he worked for a high level Canadian security organization, and how he was responsible for firewalls. He spoke to me of virtual private networks, fibre-op and their vulnerabilities.

“So yeah, I work from home in my underwear in the morning and have a sip of Crown Royal around 10:00 am,” he says to me, as my mouth drops even more. “So I often show up to work in the afternoon looking like this (a dumpy surfer-biker) after having a few drinks. I then put in four hours, and go home.”

Andrew Was Valuable, and Didn’t Need to Impress Anyone

Andrew obviously had a really good understanding of his value to his organization. He knew that that his skill of securing servers from hackers was important enough that he wouldn’t get fired for showing up to work slightly buzzed and in flip flops.

The thing I thought was really interesting about Andrew, is that he was very proud of the fact that he could pull off dressing badly for work. His wardrobe essentially says “I’m so good at my job, that I can dress like a slob, and people have to go along with it.”

Bill Bellichick’s Hoodie and GQ’s Worst Dressed Nerds

A famous example of someone who can dress however they want because they’re so valuable is Patriot’s Head Coach Bill Bellichick. When you make five Super Bowl appearances, and win three of them, people tend to let you do what you want. What Bellichick wanted, was to wear (famously) the same ratty hoodie, with cut-off sleeves, to every single game.

Bill knew his immense value to the Patriots, and liked wearing his cut-off hoodie.

There are many famous examples of this from Silicon Valley. Apple Founder Steve Jobs always wore sneakers with a turtleneck. Twitter Co-Founder Jack Dorsey used to have a nose-ring and blue dreadlocks. Facebook CEO Mark Zuckerberg rarely gives an appearance in something other than jeans and a t-shirt.

The trend of valuable employees dressing poorly is so well-known that three years ago GQ put out a list of the 15 worst dressed men in Silicon Valley.

Ultimately, I think being on that list is more of a testament to the value and status of the individual and their status at their company, than it is a commentary on fashion.

In a sense, being the worst dressed person in the room can now mean you're the most important person in the room.