The Entrepreneur’s Costume (Hint: Dress Like Your Brand)

Some entrepreneurs spend more time picking out a Halloween costume than they spend developing their own personal image. Even women, who traditionally allocate more time and energy to their appearance, often follow trends or societal norms when choosing a personal style, which is nuts, because then they just end up looking like all of the other women at the table. Brand before fashion, people!

Whether you like it or not, you are your brand. Even if your business is not centered on your expertise, you still have to represent your company in meetings and at public events. Even if you’re an über geek with serious agoraphobic issues you still have to Skype from time to time, and when you do, you better “look the brand.”

My company is not a three-piece-suit company, so I don’t wear one. Ever. I know what my brand message is, and I dress to fit that image— all of the time. Message. Consistency. Message. Consistency. The most successful entrepreneurs in the world know to follow these simple rules when walk into their pimped out closets every morning.

Take Martha Stewart. Her everyday look is the same as her on-screen, in-print costume: country estate meets self-made media mogul. Orange jumpsuit aside, she dresses to suit her carefully planned image for every occasion.

Or look at Hugh Hefner. From the beginning he dressed according to the Playboy image, complete with James Bond suits and velvet smoking jackets. You’re never going to see this guy in sweat pants or Bermuda shorts. His look is so consistent, so famous, people actually show up for Halloween as Hugh Hefner. Now that’s a costume.

Dressing like your brand goes beyond consistency. Martha and Hugh dress not only according to their company’s image; they dress to embody the aspirations of their target market. Martha wears her tailored suits and cashmere sweaters to appeal to every wannabe domestic goddess. And Hugh dresses like he either got some, is about to get some, or both, which plays into men’s fantasies— not that I would know that or anything.

When dressing like your brand, remember to think about the whole picture: hair, shoes, jewelry and other accessories. Richard Branson, one of the most successful entrepreneurs, dresses to the spirit of his brand: adventure. He’s a bit of a rebel, and he has the hair to prove it. When people see a picture of him they get him, and more importantly, they get his brand. That’s why you’re never going to see him with a crew cut.

So, are you dressing according to your company’s image, or are you showing up to Chamber of Commerce meetings looking like a schlub— or worse, like everyone else?

This upcoming Halloween, and everyday thereafter, go as your brand.


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