Tell us the story of your f#cking hat, bro

Here's who you are when you wear one of those tricked-out flat brimmed hats

I had been seated for long enough that the biting, eye-watering smell of the sanitizer packets that flight attendants once forced into the hands of every passenger that now only celibate germ-freaks still compulsively use to wipe every touchable surface of their tiny non-refundable basic economy flight experience had almost dissipated. I was engrossed in reading and re-reading and re-re-reading the same verbose, self-indulgent, incomprehensible run-on sentence of the vanity book I brought and would probably never finish when the seat directly in front of me lurched back with the impact of probably the last passenger to board the plane. I looked up with an exaggerated frown that no one saw, wondering who had never been taught how to be seated in a public space without causing an earthquake, and then I saw it. That fucking hat.

There is a certain type of hat that says literally everything there is to be said about the person wearing it. Allow me to educate you.

The brim is as wide as a Bushwick polycule and as flat as the topline revenue growth of yet another ashwaganda cacao adaptogen drink powder. The crown is taller than it needs to be, perhaps to add compensatory height to the wearer, or to symbolize the vast expansiveness of his irrationally liberal world views, or just to leave room for his loosely tied, unwashed man bun.  

The starter kit hat is usually black, but more advanced wearers opt for shades of gray – sorry, heather granite, tan aka cafe latte, and sometimes green – er, loden sea moss. There are also burgundy varieties of this hat, but anyone wearing a burgundy flat-brimmed hat already has no fewer than thirty in various shades of black, gray, cream and green, with a retail value greater than a mid-range BMW.

There are a number of types of material out of which these hats are made, the most basic of which is humble felt. People who wear felt hats have only just begun their journey into insufferability and naval gazing, but once their life coaching practice or DJ career provides more financial abundance, they will upgrade to a hat made of beaver. People who dive head-first into beaver (lol) are either recovering software entrepreneurs who have just sold their VC-backed fintech company to PayPal for $300 million and wish to differentiate themselves from their uptight Stanford MBA cohort and also attract kundalini yoga instructors they meet on month-long surf retreats, or they are recipients of cripplingly large trust funds and have never had to shape their own identity, so they simply purchase it at stores in Roma Norte, Oaxaca or Bali. It is important to note that entrepreneurs who have three-comma exits do not purchase these sorts of hats, because they tend to blow off in the Mediterranean breeze on their custom Italian yachts and are blue state aberrations of the more traditional western hat worn in Aspen, Jackson, Telluride (“Telly”), and Sun Valley by well-heeled democracy abolitionists.

Everyone who wears these hats would be entirely indistinguishable from one another were it not for the embellishments wrapped around, glued onto, and needled into the trim and even crown of these entirely vestigial, insouciant head coverings.

A critical, even spiritual part of the acquisition process and an essential incremental revenue generator for the English-as-a-second-language (this is mandatory) vendor, these embellishments provide limitless optionality and often require years of consideration, which can understandably justify work sabbaticals to containerize long periods of stylistic meditation. Materials, under pain of excommunication from The Community, must always be naturally occurring and ideally “found” or “gifted.” For people incapable of listening to other people speak, these embellishments give the wearer lengthy topics of one-sided conversation to be had over a beach bonfire built by underpaid Nomade hotel staff in Tulum or an overpriced Gaggenau natural gas fire pit next to $23 million beach cottage in Montauk.  

Now then.

Having established this context, on to the inevitable story of the hat blocking my fucking view of the breasts of the flight attendant showing absolutely no one how to buckle and unbuckle and buckle again their seatbelt.

This particular upside-down shaman-douche brain-bathtub was a lighter gray, which someone tedious might call Distressed Heather Ecuadorian Autumn Storm Cloud. It had the typical flat brim and tall crown, which, based on the skyward tug of the dark brown hair beneath it, indeed concealed a man bun. There were all kinds of stones and twine and feathers and berries and bugs and god knows what the fuck else burdening this hat. How the weight of all of those vibes didn’t crush his vertebrae is an orthopedic miracle.

Because just the hat alone – with its $4,000 of customization – wasn’t distinct enough to pinpoint exactly which Burning Man camp the wearer had claimed to have co-founded along with someone who actually did all the work, he had also wrapped his sea salt and coconut oil seasoned hair in a bandana. It was blue and looked as if it had been through a tornado, a tsunami and a shark attack, which meant that it had been purchased at a boutique in the seedier end of Venice Beach for $235.21.

I stewed with disdain in my featherweight Patagonia travel pants and SPF hoodie, which unfortunately had the logo on the back of it. I imagined the conversation that this manchild, whose face I hadn’t yet seen, would have tomorrow at sunset on Playa Guiones with the topless kundalini yoga instructor whose two-hour performative meditation he would interrupt.

“Hello,” he would breathe in the quiet, sonorous, baritone that he had conditioned down from a tenor through years of breathwork, Adams apple steroids, and gazing at himself longingly in the mirror. “I couldn’t help but notice how beautiful the sunlight is on your eyelids.”

The yogi would open her eyes (which she always explains with feigned humility are either hazel or green depending on the color of the Alo Yoga unitard she wears that day), conceal her outrage with a serene smize, and then slightly curl the corners of her subtly injected lips to suggest a tenuous inner peace cultivated from the countless times she had sat in Ceremony.

“Oh wow,” he would say, nodding his hat-covered head slowly and wisely, flashing a toothy white smile, freshly free of the 3-year purgatory of his Invisalign trays and only minutes out of top and bottom Crest White Strips.

“I love your hat,” she would say, instantly giving him a half erection and cueing a story he had told three-hundred times two and five hours prior to engaging in mostly unprotected sexual intercourse with story recipients.

“Thank you,” he would say, lowering his big brown eyes as he ran the long, heavily ringed fingers of his right hand up his perfectly oiled ten-day beard. “I had it customized by a guy in a little indigenous village just outside Oaxaca who used to work for Alberly and went off on his own.”

“Wow,” she would nod, raising her eyebrows just enough to feign interest but not so much to tax her dwindling Botox treatment.

“Yeah,” he would reply, oblivious to her averting her gaze to the Costa Rican surf instructor emerging from the water, whose glistening torso is as totally shredded as a parking ticket on one of Elon Musk’s McLarens.

“I like the matchstick,” she would offer, optimistically wondering how much he had sold his fintech company for and whether or not his vintage blue-faced Rolex was a gift from a much older fashion publicist ex-girlfriend or if he had actually bought it himself.

“It was gifted to me in a peyote ceremony in New Mexico,” he would say, now entirely erect thanks in equal parts to his vanity and the ten milligrams of Cialis he had taken before scouring the beach for kundalini yoga instructors. “I sat with a tribal elder for a whole night, like, learning from his generational trauma and just like sweating in total silence. It was so hot in there.”

“Wow,” she would reply. “Intense.”

“Yeah,” he would nod, wide-eyed, slightly adjusting his Indian style sit pose to center on his perineum and showcase his erection through his retro thrashed Japanese archival vintage denim acid washed jeans. “When the sun rose, he gave me this matchstick and told me that it was the icon of my eternal power to provide warmth and sustenance and light to my partner and my unborn children, and that it symbolized the ignition of my masculine energy and the heat of my passionate soul.”

“Wow,” she would reply. “Intense.”

“He was so old and wise,” he would add. “Like, I could see his lineage in the flames of the fire reflected in his indigenous eyes.” She would nod her head slowly, pretending to absorb the words in this panty-dropping ritual. She would notice but not notice his erection, which significantly improved his chances of getting laid if he had indeed been the founder of a successfully exited fintech company.

“Where did that feather come from?,” she would ask, now mocking him but also slightly curious about the elaborate story he would word-vomit at her. She didn’t have dinner at Coyol with her hedge fund manager client for another two hours, so she was here for it.

“Ah,” he would smile, “I was walking through the jungle in Peru at dawn, integrating after my tenth ceremony that week, and I noticed, like, a Jacobs ladder in the path ahead of me,” he would say, “and at the top of the trees in the center of the light I saw this like, magnificent white bird, and it was fully staring at me as I respectfully walked towards it–”

“Wow,” she would interrupt, needing to make affirming noise. “Intense.”

“—it’s silky feathers shined in the dawn of the day of my cosmic rebirth,” he would continue, “and I slowly raised my arms as an offering of love for this beautiful avian creature, feeling connected to her through the Grandmother in my veins, and the bird like fully took off and flew right over my head and kind of like, hovered above me for what felt like hours, and I closed my eyes in gratitude for the bird-wind on my human skeleton and then it flew away as if like, called back onto her celestial highway, but as I watched it leave my sacred space I saw a single feather falling from the sky through the sunlight, and it landed directly between my eyes, and I like stood there with my eyes closed for what felt like hours, just feeling grateful gratitude for this blessing.”

Here he would pause, looking wistfully out to the ocean, hoping he could summon at least a bit of moisture to his eyes if not a tear, which he had done by the pool of his hotel last week in Holbox. It had fully created a vulnerability umbilical cord between him and the kundalini yoga instructor with whom he had then had consciously unprotected fluid-bonding sex following her primary partner’s verbal consent and agreement to photograph.

 “Wow,” she would reply. “That’s intensely intense.”

He would look at her, just with his eyes, his face still angled to the ocean so as to keep his skin optimally illuminated by the waning sun, which was receding from this conversation just as fast as the rotation of the earth would allow it.

She, a veteran sparkle pony since graduating from the University of Arizona and assuming control of her modest trust fund, wondered if his Burning Man camp had a good chef and if he had a two-bedroom RV with really good air conditioning and built-in Hepa filters.

He, without being asked, would then explain the origin of the last mystery of his hat.

“The red thread,” he would begin followed by a very deep breath, “yeah, that was from kabbalah bracelet that my ex-partner unraveled for me following our conscious uncoupling,” he would confide.

Her eyebrows would raise as high as her Botox would allow, wondering where the actual fuck this story was going to go and why he would bring up another fucking kundalini yoga instructor before he had even kissed her Yoni.

“We met on the beach in Tel Aviv and backpacked from kibbutz to kibbutz all over Israel for four years before we moved to Cape Town to start an adaptogen cacao maca powder coffee company that we sold –“ to a morally bankrupt multinational conglomerate single-handedly responsible for deforesting 38% of the rainforest and allegedly poisoning an entire kindergarten class with bad chocolate milk mix “—but our financial abundance revealed divergence in how we wanted to manifest our sensual lives in terms of ethically non-monogamous partnership, so we consciously uncoupled” and spent the majority of the proceeds of the fire-sale of the company on legal fees.

“Wow,” she would respond.

The sun was now entirely set, and the two of them were illuminated only by the gray sky, a similar shade to his distressed heather Ecuadorian Autumn storm cloud hat.

“I’d love to drop in and deep dive with you more,” he would say, optimistically. “Would you like to get a matcha at my hotel?”

“I’ve already had a few matchas today, and it’s a little late for caffeine,” she would reply, unapologetically, “but how about you come to my kundalini yoga class tomorrow at 5am.”

“Wow,” he would respond. “Intense.”

Just as they both stand to consciously uncouple from the drop-in I’ve imagined, the plane we are on drops down to the earth in real life. We taxi for all of three feet, because planes at small Central and South American airports land no less than half a mile from the terminal to make overdressed tourists sweat in the tropical heat while airport staff smirk and snicker at particularly obese Americans.

Just before the seatbelt sign darkens and that ubiquitous ding breaks the silence, catalyzing a stampede into the aisle, I wonder if he’s even wearing shoes. Men with hats and bandanas never wear shoes, I reflect.

The ding dings, and he and I stand simultaneously. He’s a few inches taller than me, and when he turns to face the overhead compartment to unstow his well-worn Carhardt backpack, I see that he is annoyingly handsome and has that kind of beard growth that looks patchy in a really sexy way. Like, it just fucking grew once, when he was nineteen, and he literally never had to touch it again. I bet he’ll never have a single hair on his back, I think to myself.

As he throws the backpack over his naturally muscular shoulder, I see that his hands are enormous and his silver rings, which appear large enough for me to wear as a cockring, are annoyingly tasteful. His thirty-two bracelets, which appear to have been harvested from artisan markets literally all over the world with a patina from spear fishing in all five oceans, are also annoyingly tasteful.

As we exit the plane I cannot decide if I am infatuated with or absolutely despise this man, who I reassure myself is a total inarticulate dick void of culture and substance.

As he precedes me down the intentionally treacherous metal steps of the mobile staircase, I notice the matchstick again, rising out of the red twine around his hat. I allowed a number of thoughts to pass through me like venomous bubbles in a pool. What are you going to light with that match, bro? Some fucking ceremonial-grade palo santo? A bunch of sage after your threesome with two kundalini yoga instructors? Or maybe you’ll light their hand-rolled cigarettes made of Danish tobacco wrapped in a fair-trade papaya leaf on a pile of bamboo yoga mats. Do you tickle your taint with that feather while you take Polaroids of yourself?

I marvel at the symmetry of his face each time I pass him in the customs line. He is a beautiful man, and I resent him, and he probably has an illegitimate child in a developing country.

I make it through customs, forgetting to say pura vida to the passport stamper, and walk to my group of friends. We find our shuttle bus driver. I wonder where my woke nemesis has gone just as he walks up to us, overloaded with water and delicious high-sodium snack foods from the airport convenience store.

“I got hydration and snacks for us,” he says to literally all of the people I know. And then he looks at me with his big, beautiful, soulful brown eyes – eyes that have deservedly dropped hundreds of Lycra yoga bottoms.

“Hey, we haven’t met yet,” he says to me, maintaining intense but nonthreatening eye contact. “I’m David.” He extends his giant hand and I take it, offering my name in response, trying not to seem like a doe-eyed kundalini yoga instructor.   

“I’m glad to meet you,” he says, “looking forward to hanging in paradise.”

Standing in his gaze, I realize that every story I imagined in my head about his magnificent, authentic, thoughtfully curated hat probably pales in comparison to its real origin story.

“I love your hat,” I say, batting my eyelashes. “What’s the story behind the matchstick?”