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Why You’re Dressing For Success All Wrong (And What To Do Instead)

This article is more than 4 years old.

At the age of twenty-two, I decided to save rock ‘n’ roll.

This was in 1999, the year Limp Bizkit and other bro-metal bands ruled the charts, and I hated it. In addition to the horribleness of their sound, their disregard of all that was glamorous about the music I loved was insulting to me. So, I wrote a bunch of songs, got a group of guys together who saw the world the way I did, and put together a stage show that would serve as a corrective to the times.

We had lights. We had confetti cannons. We even had a friend who danced in a cage wearing a gas mask. And we dressed awesome. Tight striped pants. Ascots. Pointy boots. Top hats.

It was a lot of work for a bunch of young scrappers, but we made it happen. We imagined the fantastical onstage world we had concocted to be the next in a line that included David Bowie, George Clinton, and Devo. We wrangled our first gig, called everyone we knew, and got them to call everyone they knew. We were convinced that when people saw our outrageous stage show and flamboyant outfits, word would spread throughout every corner of New York City and beyond.

That’s not what happened. Even though the people we invited seemed to have a good time, the shows that followed were sparsely attended. As the months went on, it was clear the problem wasn't getting any better.

As a student of rock ‘n’ roll, I knew image was everything. As such, I figured if we dressed like rock legends on stage, we would become legends. What I failed to realize was that true rock ‘n’ roll stars have never drawn a distinction between stage and street.

I was a different story. My wardrobe was full of all kinds of clothing I had accumulated over the years during various phases of my life without much consideration. Khaki pants. Baggy jeans. Banker-blue button-down shirts. When I was onstage, I was a rock god. In my day-to-day life, I chose what to wear by grabbing whatever happened to be clean.

Because the Lower East Side music scene was tight-knit, people undoubtedly noticed the contrast. As a result, my front man act came across as bogus. Even though we were putting on an entertaining show, we lacked the commitment to carry it through in the rest of our lives. We dressed for the moment but didn’t use our clothing to tell a story. And that was where, at least in the beginning, we fell short.

Dress For Success The Right Way

In the years immediately following World War I, a young German playwright from an upper middle-class background decided Communism was his jam. His name was Bertolt Brecht, and despite his attraction to radical equality, it was incredibly important to him that name appear in lights. He realized, however, that his biting dramatic critiques of capitalism would lose all legitimacy the moment anyone discovered the real story of his upbringing.

Bertolt Brecht, every bit as talented a self-promoter as he was a playwright, set out to insulate himself against this threat. He did so by meticulously crafting an external persona that screamed working man. He filled his wardrobe with the shirtsleeves and leather caps typically worn by mechanics and factory workers. He consistently sported a three-day stubble. He wore simple wire rimmed “austerity spectacles.”

Brecht was as concerned with dressing for success as any Fortune 500 CEO, and his view of how to do so was remarkably shrewd. He could have chosen to wear variations on the same kind of outfits that the other intellectuals and writers in Weimar-era Germany favored. Instead, he used clothing as a mechanism to control how he was perceived. He had a certain image he knew was essential to his success, and he used what he wore to ensure this was the image people associated with him.

What made Brecht's strategy work so well for him was that he committed fully. He didn’t only wear his worker’s uniform on the opening night of a new play or in interviews but instead sported his signature uniform at all times. In doing so, he became synonymous with the “working man’s playwright.” It's how people still think of him today. 

Use Your Clothing As A Tool

Even though I had no clue who Bertolt Brecht was in 1999, my disappointment with how our band was going eventually drove me to form a philosophy of fashion that was similar to that of the notorious playwright. After playing a year’s worth of sparsely-attended shows, I filled a trash bag with all my khakis, button downs, and functional shoes and hauled them down to the local Goodwill. I figured that if I was going to save rock ‘n’ roll, I should try to be a little better about living rock ‘n’ roll. From that day forward, I told myself that there would be no distinction between what I wore on stage and what I wore when walking around.

And you know what…it worked. We started to see the same faces at our shows again and again. Eventually we got a residency at the legendary New York venue Arlene’s Grocery and then sold it out on a Wednesday night. We even recorded with the guys who had produced Sonic Youth and the Ramones.

Did we go on to play Madison Square Garden, hit number one on the charts, and embark on a decade-long sprint of decadence and debauchery? Nah. Turns out, it takes a lot more than clothing to drive rock ‘n’ roll stardom. That said, the strategy helped me—a third-rate guitar player who can barely sing—to get closer to being a rock ‘n’ roll star than I had any right to expect. And as I moved into the next phase of my career, the lessons I learned about how true stars in every field dress for success have stayed with me.

Whether you like it or not, clothing is one of the most important markers of what you stand for. Since people can’t crack open your skull and peer into your mind, they use the wrapping paper you choose for yourself to make judgments about you. Most businesspeople don’t understand this. They view dressing for success as wearing a suit and tie to business meetings. Or maybe they dress in a blazer and new sneakers to show how creative they are, even though everyone around them is doing the same.

Instead, think about the message you want to convey about your talents, your abilities, and your demeanor. Then choose your clothing based on that. Make choices about what you wear in light of crafting a persona that is immediately identifiable with you and you alone. And stop drawing about a distinction between work clothes and every-other-time clothes. If you’re serious about being successful, you need to become famous in your niche. And every famous person has a look that is theirs and theirs alone. That is what dressing for success is really all about.

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