“It’s not going to button…” my wife Georgie says, stifling laughter as she wrestles my shirt collar. It is 10 p.m. on a Wednesday night, and I have wisely chosen this moment to attempt a high dive into my wedding tuxedo—but I’m ten pounds off the mark.
“Use some elbow grease!” I choke out, trying in vain to suck in my neck fat. No dice.
Dressing up conjures a mixed bag of emotions for me. My vanity swoons at the idea of velvet slippers and a clean, James Bond–style tuxedo—glittering cufflinks and crisp collars. My semi-feral insides recoil, longing for dirty jeans and an eBay T-shirt. Budweiser over Old Fashioneds.
Like Dr. Jekyll and Mr. Hyde, I rage against myself while getting ready, vacillating between manic ego-stroking and soul-crushing pessimism. However, once the deed is done and I take my final plunge into the mirror, I feel at home—even if I resemble an overstuffed sausage.
The black-tie event in question was a magical evening at the Explorers Club in Manhattan, hosted by Outpost’s founder, Ryan McMahon. As many of you know, Ryan is an arbiter of all things cool and class, and this event had an excess of both.
Stepping out of our yellow cab that evening, the club’s double doors swung open, and we were greeted by Oriental rugs, dark walls, and the faint smell of woodsmoke. In the lobby, attractive young couples slipped out of their rain-flecked coats, making final adjustments before ascending the stairs to the cocktail party.
The bar was well stocked thanks to our friends at Blade and Bow Whiskey, and as people imbibed, the room filled with conversation and laughter.
Seeing my competition, I started to sweat. I had just noticed a faint stain on my lapel—a hastily paper-towel–rubbed dot of hummus from a wedding in October—and I was certain I would be flayed for the faux pas. Georgie, naturally, was a vision: calm and beautiful, floating between guests while I fidgeted at the bar.
Despite my paranoia, the hammer never dropped. People greeted me with smiles and hellos. They were even kind enough not to mention my mismatched cufflinks. That first Old Fashioned went down like honey, and suddenly, I was comfortable.
Dinner was quite literally rung in by Ryan, who had the privilege of sounding the ceremonial bell. After a brief round of applause, we filed into the dining room. The tables were long and flickered with candlelight, catching the women’s earrings and lips. The whole room shimmered.
After a simple yet filling dinner, Ryan stood to give a speech. He opened with a story about a frustrating experience during New York Fashion Week. He had planned to attend an event for J.Press, a brand he has long admired, and despite purchasing a ticket, adjusting his schedule, and waiting in line, he was turned away at the door—they were “at capacity.”
Now, I know what you’re thinking. Some of us more unhinged folks might have gotten physical at that moment, but Ryan calmly left and instead came away with a realization.
That event was everything he didn’t want Outpost to be. In a cultural world swirling with different voices pushing art and media and leisure and travel, there is a self-seriousness that undercuts their inherent joy. Ryan believes Outpost can be a panacea to that self-seriousness—a refuge for those looking for something they don’t quite know how to define.
The room broke into applause again, and Ryan sat, finally able to enjoy his evening with the hard work behind him.
As the evening waned, people milled about, finishing their wine and charting the rest of their night in whispers. Some sat, some stood, but the room bloomed with a satisfied quiet. Georgie had gone to get our coats, and I slipped outside onto the balcony for some air. The night had grown cold, and I flipped up the collar of my tuxedo as I nursed my final cocktail and watched the partygoers inside. Suddenly, Ryan’s speech came back to me.
I think part of the reason I buck at the idea of putting on a tuxedo—or a suit, or even a collared shirt—is because it feels like I’m putting on a costume. For a brief moment, I’m sacrificing a shred of individuality to blend into a crowd. This isn’t a statement about how unique or special I am, but rather an admission of how often I feel unworthy of certain status symbols. Black tie is meant for a particular kind of person: a man who sets his watch, balances his checkbook, has a high-end job, and can tell you what NASDAQ stands for.
But tonight, dressing up felt different, maybe because Outpost is different. It’s not about status or showing off or being someone else. It’s about joining a group searching for the same thing—refuge in something hard to define.
In the end, the joy of dressing up is doing it with a crowd where you feel you belong. And what a joy it is to belong.
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