The Case Against Wearing the Same Thing Everyday … and for Wearing Ties

“What do ties matter, Jeeves, at a time like this?’ There is no time, sir, at which ties do not matter” P.G. Wodehouse

Successful people generally find a style formula that works for them and then stick to it without getting too distracted.  For Mark Zuckerberg, that means grey t-shirts and hoodies. For President Obama, that means blue and grey suits. The point of this is to settle in on a sartorial aesthetic that pleases you and helps you to be your best self.  The cultural context matters (despite the fact that many wish it did not).  How people perceive your aesthetic might be very different from your perception.  For instance, in Silicon Valley, wearing a t-shirt, hoodie, and cargo pants might communicate the message that you are pragmatic, honest, and competent.  In Washington D.C., the same outfit might communicate that you are on vacation.  Billionaires and Presidents do care about what their clothes communicate, otherwise they would be ambivalent rather than intentionally minimalistic.

“You know, they come up to meet me – a lot of the guys from Silicon – and they’re wearing undershirts. I could tell you a story. Some of the biggest in the world – they’ll come in on roller skates.”   Donald Trump

But let’s step back from the minimalistic option for a second and consider the other end of the spectrum.  My friend Phil Cohen, a fashion blogger and graphic designer, enjoysa wide variety of clothing options (albeit still with a unifying aesthetic). Another friend,Camille Tutti, Executive Editor of NextGov, posts shoe selfies to Instagram, or “shoefies” as she likes to call them, as she covers innovation and government news around town.  My buddies over in Georgetown, including Chris Kaufmann and Jack Eggleston will help you put together a professional wardrobe that both expresses personality but also keeps things simple so you can focus on work.  For them (and for me), having a little variety in the wardrobe, just like varying your menu or your music, keeps things human.  Sure, uniforms serve a valid purpose, and every fashion is a uniform within its own aesthetic, but humans are inherently creative.  The balance between compliance with social norms (whether justified through pragmatism or passion) and creative individual expression is one which can (as Zuckerberg points out) keep us from accomplishing more important tasks.  But denying ourselves from acting on certain creative urges can also hold us back in other ways.

The bottom line – If clothes can be used to help us become our best selves, it begs these questions:

  1. What is your best self?
  2. How does clothing affect your progress towards your best self?
  3. What is the appropriate amount of time, money, and effort to invest in clothing in light of the first two questions?


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