There is a new unwritten rule amongst big tech CEOs: the more you dress like you're homeless, the more powerful you are (or are perceived to be). Dennis Crowley of Foursquare is a recent offender but it rolls much deeper. Going to a technology conference these days, you see more tees and hoodies than at an American Apparel. We're not talking business casual here, we're not even talking weekend casual, we're talking house painting attire.
So what's so wrong with being different? Not everyone needs to wear a suit, nor should they. The problem is that these CEOs attire at big public events, news conferences and during television interviews are so casual that it smacks of arrogance. Interviews are important, speaking at conferences where thousands of people are listening to you is important, and yes, being a professional role model to the people that work for you is important too. These things matter, dressing like they don't makes it come across like it's all very beneath you.
We get it - you can be both powerful and young, you are different than your dad, and you started your company in college when these were perhaps the only clothing choices you had; but here's the thing, dressing like the "everyman," doesn't make you the "everyman." You are in fact "the man". You control billions of dollars and thousands of livelihoods, people want to hear what you have to say and look up to your brilliance and tenacity. Own it (with the occasional button down).
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