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My fifty-year-old barista brother is such a mess that you can't tell if he's a hipster or homeless.

It is so bad that strangers will cross the street to avoid him. Personally, I think he’s having a mid-life crisis and trying to alienate friends and family. Please, I need some words of wisdom to inspire him to clean up and get his act together.

~ Rob


The aging hipster is not an easy role to play. Once that big old beard starts to turn gray, the hair begins to thin, and the suspenders fray, the trendy barista can look decidedly grizzled. And God forbid an accident happens.

Being over fifty-five, a klutz, and a bit of an expert at being rushed to the ER, I have a thing about always going out of the house looking your best. It’s that just-in-case insurance for untimely visits to the hospital. Call it a hunch and call the world unfair, but I reckon ER doctors and nurses work harder for the well-kempt old guy screaming in pain rather than the bedraggled one. (Especially, if you’re on a gurney in one of those unsightly baggy blue robes that tie in the back.)

The clothes we wear, whether healthy or not, are the first to announce to the world where we fit in. We dress ourselves, as some social psychologists say, to confirm the version of our present-day selves. It’s called congruency theory and it simply suggests we try with our outward appearance to advertise to ourselves and others the best version of who we are. The movies do it too. In cahoots with the director, producers, and lead actors, this is where the costume department tries to make the ideal sartorial version of the character. This is serious business with Academy Awards for those in Hollywood who do it best. These costume designers in effect build characters.

Meryl Streep is quoted in a New York Times article about Academy Award-winning costume designer Ann Roth (whom she’s worked with many times and now plays the old “beautiful” woman on the bench in Barbie) saying, “You just remember the people she has clarified for you through what they chose to put on their bodies in the morning… Authenticity and specificity.” For Ms. Streep and other actors, this wardrobe business is all about supporting the story and clarifying a look that is unambiguous and sells what their character and the narrative are all about.

In bad movies, the actor’s look can derail things. The wrong decisions lead to confusion among the audience. I experienced this myself with a movie I made where we dressed the Warren Beatty-inspired lead in such fancy clothes that some in the audience thought he was gay. Not helpful, when the sex comedy you’re making is trying to make a point of untethered male randiness of the hetero variety.

It happens in real life, too. It reminds me of the infamous film director in Hollywood who goes to Academy screenings carrying his guitar and a soft briefcase overflowing with papers. His beard, wild shock of long gray hair, and well-worn black denim give off the whiff of an ad exec who sleeps in his car. Of course, he doesn’t but to the untrained eye or someone who doesn’t know him…

Bad movies and judgment aside, there are two possibilities here. First, it seems your brother is reflecting some story problems in his dress. (If his life was a movie, we’d probably be at the beginning trying to understand his unfinished business.) There is an adage in drama, that character is action, which, in my mind, extends to the smaller details in our lives. For example, character also could be how messy your room is. This is not earth-shattering news for Marie Kondo fans. Still, it does beg the question: If character is action and is reflected in how slobby you are, or the clothes you wear, then the story must change for there to be a change in some of the details, correct? This all, of course, is assuming that looking homeless is such a terrible thing, which brings me to the other possibility: maybe he’s just a bad dresser. But probably not. He's a hipster!

My guess, given that he was a proto-hipster and gave what he wore quite some thought, is that today’s sloppy outward presentation has something to do with his story. Taking what Meryl Streep suggested in her comment about being dressed by Ann Roth, perhaps his look is trying to clarify or subtly announce a certain challenge or change in his situation. With that in mind, maybe the tact is to sit down and get to know your brother a bit better and work from the inside out. Try to see what’s going on internally rather than worrying about others making snap judgments about his outward appearance. For example, that director I mentioned who seems to be going home to his car… He is a famous director living in a huge house who once had a famous fight with a studio and lost. I’m not sure if he’s worked much since but with the way he dresses there is still some defiance lurking. It’s kind of inspiring; rather than pretending all is good, he is, in some ways, expressing that the good fight continues.

Your brother's story, I’m sure will be full of surprises and, hopefully, with some brotherly-producer advice, his wardrobe will either make sense or change with some new story ideas. Of course, if he’s just letting things slip, then just remind him: You always want to look good in the movie you’re starring in– especially over fifty– in case you end up in the hospital. You don’t want the harried ER doctor pulling up to the nursing station and delivering the line: “Where’s the homeless guy’s chart?” Unless and quite rightly, the nurse answers, “You mean the hipster?”

Andrew Ainsworth is the author of the “endlessly interesting” self-help book Blockbuster Living: Making Your Life the Best Movie You’ve Ever Seen, which can be found on Amazon. He currently lives in Culver City, Los Angeles, a block from where the Wizard of Oz was shot.

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