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Whiskey With A Side Of Shopping: The Masculine Utopia Of Trunk Club

It’s tempting to think of Trunk Club as a well-marketed service for rich, busy dudes — a way to make clueless, frumpy men into well-dressed lazy ones. But is the masculinity that Trunk Club sells worth aspiring to?

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It’s sprinkling outside on an early April day, but inside the Trunk Club clubhouse, it feels like deep fall. The couches are dark, pocketed leather; the bar is a rich walnut and, according to the receptionist serving as temporary bartender, fully stocked. It feels like man in here. Or more precisely: It feels like man-with-a-lot-of-money in here.

As I wait for my glass of champagne, a lithe, chirpy woman enters the room.

“Has anyone seen my fellow?”

Her fellow: Trunk Club for “client.” It’s one of many aphorisms, including “trunk” for a cardboard box of apparel and “clubhouse” for a Midtown clothing store, that work to transport the consumer to a time when real men wore tailored clothing.

Each “fellow” arrives at the Trunk Club office and is ushered through a frictionless shopping experience that feels much more like a date than shopping. An IPA or whiskey poured in the man room; a tour of the “Mansion on Madison,” into which Trunk Club moved just this fall; the decadent, Instagram-ready rooms that fill each of three floors; and a casual conversation that feels more like flirting than a fitting.

Right now, the clubhouse experience is still limited to five urban areas (New York; Dallas; Chicago; Washington, D.C.; and Los Angeles) and makes up a relatively small percentage of Trunk Club’s overall client base. But that experience of effortless shopping is baked into every shipment.

The at-home Trunk Club experience is straightforward. Sign up online, set up a phone conversation with one of dozens of stylists who dot the country, and a 30- to 40-pound box will arrive on your front door, packed with dress shirts, “quality denim,” hoodies, socks, even boxers. The user tries the items on, tells his stylist what he likes, and sends the rest back. With each Trunk, the stylist will get better at zeroing in on the user’s specific tastes and fit; eventually, the logic goes, the trunk will magically, effortlessly, fulfill the client’s every fashion need. It’s not the end of shopping; it’s the end of thinking about shopping.

Or so the theory goes. But the through line of the Trunk Club experience isn’t just the self-replenishing closet. It’s a throwback to an earlier time in retail, and the look it promises for its clients is one of very traditional respectability — and masculinity.

In the flattering, forgiving light of the Trunk Club brand and experience, it’s tempting to think of it simply as a well-marketed service for rich, busy dudes — a way to make clueless, frumpy men into well-dressed lazy ones. But is the masculinity that Trunk Club sells worth aspiring to?

The CEO of Trunk Club, Brian Spaly, looks a lot like a Ken doll who just got off the beach. He has chin-length hair he tucks respectably behind his ears, a slight trace of a stubble, and a constant tan. He’s as impeccably dressed as one would expect from a man who’s launched not one, but two successful men’s clothing companies.

His first project, Bonobos, was a collaboration with Andy Dunn, offering a hipper, mail order–only alternative to J.Crew. Spaly left Bonobos in 2009 to take over Trunk Club, which had started as a brilliant idea, conceived of by Joanna Van Vleck, a 25-year-old University of Oregon business student, but was floundering as it attempted to expand.

Spaly helped resurrect the struggling company, growing its stylist workforce, brand offerings, and clubhouse presence. Today, Van Vleck has been excised from the Trunk Club narrative, especially after it was acquired by Nordstrom for $350 million; the aura that clings to the brand is one of unflappable coolness. Just look at the company's Chicago headquarters: straight-up West Elm–ed whiskey bar.

“Guys hate shopping but want to look good” is the one-sentence Spaly sales pitch, repeated in nearly every interview he gives. It’s an essentialist statement that nonetheless gets to the heart of a very American desire: Men want all of the privilege that attends fitting societal norms, but want to perform none of the labor that would accompany it.

Men with enough means have always been able to outsource this labor: to personal shoppers, of course, but also to assistants, wives, and doting mothers. But a number of shifts in the retail market, including the decline and conglomeration of department stores, have rendered personalized shopping a rarified experience. You can still get a personal shopper at J.Crew, but then you’d be the kind of guy who dresses exclusively in J.Crew.

As one of Trunk Club’s lead stylists told me, most men don’t need a stylist's help for normal suit and ties. It’s the stuff in between — the Friday night shirt, the casual weekend hoodie, the non-dad jean — that poses a challenge. And no one wants to tell a personal shopper at the department store to find them a cool hoodie. It’s somehow too old-fashioned, too 1 percent, too embarrassing.

In its mail order iteration, Trunk Club erases those negative connotations. There’s a woman picking out clothes for you, but you never meet her. She’s a beautiful voice, a cheerful text message. When you try on the clothes, you do so in the privacy of your own home, without the pressure or anxiety that accompanies the in-store experience. Returns are painless. Shipping is free. And the man you see in the mirror, post-Trunk, looks holistically hip. Take off his well-fitting jeans, and his boxers will befit the inner cool beneath.

That might not be the reality, but it’s certainly the aspiration. Because Trunk Club, like its female-directed counterparts, may ostensibly be selling clothes, but what it's really selling is confidence. That you’re wearing the right sort of shirt on your first date. That your pants make you look good — but not too good. That you’re a man whose exterior says "Take me seriously."

I saw various stages of that confidence in action during my trips to the Trunk Club clubhouse. While I waited for my stylist host to fetch me, I saw three men escorted into their initial stylist conversations. One, late twenties, was nervously fidgeting in his poorly fitted khakis; a second, in dark, perfectly cuffed jeans and expensive shoes, put his feet on the coffee table in front of him. A third I saw only from behind: They’d placed him discreetly in the rear corner, where he was sipping coffee, ankle crossed over knee, and reading the distinctive pink pages of the Financial Times.

It was like watching a video game character advance through three levels of class and assurance, all within the bounds of one room. But it’s not as if Trunk Club is using the example of older, well-dressed men to draw in its customers. For that, they have the clubhouse.

Stylists “prospect” clients by borrowing from the strategies of a real estate agent and a high-class escort. They leverage their personal networks, chat up potential clients at bars, and single men out in the line at Starbucks. They cold email on LinkedIn. They present to whole conference rooms of men at major investment firms. Once a man is in the clubhouse, his immediate response is to text his friends: You gotta see this place. Or Instagram: “Free whiskey while they bring me clothes to try on? SIGN ME. THEFUCK. UP.”

It’s not just the IPAs and leather couches. It’s the next-level male awesomeness, manifest in each of the brand-sponsored fitting rooms. The perfect mid-century-modern vibe in the one outfitted by Gant, or the massive black glass chandelier framed by a grand piano and electric guitars in the John Varvatos room. Every space has a personalized soundtrack (lots of Tom Petty, Bob Seger, and Bruce Springsteen); any sign that it’s a site of shopping is tastefully hidden. As the client tries on his new wardrobe, it’s as if he begins to blend into the backdrop of aspirational manhood that surrounds him.

Given the amount of trust the client places in his stylist, it’s natural that the relationship would become intimate. Not intimate that way — although I did observe a meeting between client and stylist, clearly not their first time together, that looked much more like a date, complete with the laugh-place-hand-on-thigh, than a transaction. Stylists told me that most clients are in relationships, sometimes thanks to them: Their stylist is their secret weapon. They text before a date, a big presentation, or their own weddings to gain her approval. “How does this look?” they’ll ask. “What shirt do I wear with these pants?”

The stylist’s hours are malleable. She has one to three clients scheduled at the clubhouse every day, and spends her off hours filling trunks for mail-only clients. Each stylist juggles email, texts, and phone calls in order to keep pace with client queries, but it’s nothing compared to the time spent with a client once he actually comes in the clubhouse, which can run upwards of three hours and as late as midnight. “We’re building relationships,” one stylist told me. “It pays to be patient.”


Online reviews of the Trunk service are mixed. “I’d say that if you’re under 5’8", picky about what you wear, or don’t have at least $300/month to spend on clothes, Trunk Club is not for you,” writes one. “I just can’t stomach paying full price for clothes ... My time isn’t so scarce that I can’t spare 30 minutes a week to browse online sales,” says another. Or from a wife reviewing her husband’s experience: “Although a bit pricey, the clothes are worth every cent. We know that with proper care, they will last a very long time,” she writes on her blog, I Love Boxes, “and I don’t list the prices of the clothes because if you have to ask, this is not the service for you.”

Trunk Club is thus intended for dudes at a certain income level, with a particularly laissez-faire attitude toward clothing. A man of average build who’s willing to submit himself to someone else’s sartorial control — and the means to fund it.

What happens, then, when someone outside of the Trunk Club ideal customer identity signs up for the service? For that task, I enlisted a former student. Hari Raghavan is two years out from undergrad, lives in Santa Clara, California, and works in communications for a software company. On paper, he’s the sort of client that Trunk Club wants to get early and while they’re still aspirational: He might just buy a few shirts now, but in five years, he’ll be relying on Trunk Club for his entire wardrobe.

When Hari signed up via the Trunk Club website, he was prompted to enter some initial information about himself. His “Work Style” is casual; his “Evening Style” is “Stand Out in the Crowd.” He wears his shirts a little loose, his pants trim, and, out of the 12 possible choices for his usual shopping, he shopped only at Urban Outfitters.

He emailed back and forth with his stylist, Lauren, whose email signature declared her a “Wardrobe Stylist / Men’s Inspirer.” When she asked him to describe his style in more detail, he replied, “My style choices tend to sit somewhere between ‘museum docent in his late 70s’ and ‘recently divorced female piano teacher.’”

It’s funny, but it’s not untrue: My most consistent memory of Hari’s wardrobe from his time as my student was a cowl-neck cardigan that would befit either of those occupations. It’s not that he’s lazy, or doesn’t know how to shop — it’s that he has, well, a sense of style. His own style.

It’s not surprising, then, that he found the first try at a Trunk “the most boring.” “It’s like they’re angling to dress me like someone’s home ec teacher,” he told me.

Hari is thoughtful and invested in his appearance and what it says about him. But he’s just a little too much of all of those things to allow a service like Trunk Club to work for him. “I like the service fine,” he told me, “and I can only say good things of the stylist — she was pretty stellar and savvy at building rapport, immediately connecting my current Bay Area situation to her own upbringing in the Valley.” (That’s a common strategy, one stylist told me — “it’s 100% like sorority rush.”)

“I wouldn’t say, though, that the trunk I was given reflected much (if anything) about me,” Hari continued. “I answered all of the questions beforehand, but I didn’t see any those answers factored into the calculus of the trunk. Everything that shipped was very generic — plain and pastel-colored collared shirts, a striped button-up here and a checkered one there, slacks, dark socks, a pair of brown boots with styrofoam soles. But I think maybe that’s the point? It isn’t so much service adapted to you, as one adapted to the 'everyperson,' to everyone. You feel like they really put thought into it because it’s clothing anyone (you included!) can wear. So yes, I felt included and appreciated."

But clothing for “everyperson” is, of course, clothing for a certain type of person: “Another thing it left me with, and I don’t know what to do with it, but I’ll include it: all the clothes given to me felt very, well, white. And I’m not white?”

So Trunk Club works for busy men who want to fulfill a certain idea of fashion and masculinity. But could it work for women who wanted to dress similarly?

When I asked Lisa Rosenblum, one of the head stylists in New York, if they ever worked with dapper-aspiring ladies, I expected a hedge. But Rosenblum’s response was immediate and encouraging: “We’ve worked with a number of women! We love it!”

I enlisted BuzzFeed’s director of podcasts, Jenna Weiss-Berman — who describes her style as “retired literary Mainer” — to arrange an appointment. Her stylist asked her many of the same questions Hari had fielded: Where do you normally shop? What are your favorite brands? How do you wear your pants?

Jenna was nervous: “I’m picky,” she told me, “they’re not going to find anything that fits me.” When we met her stylist, Lauren, Jenna’s first words were “I’m going to be your worst nightmare.”

But Lauren was undaunted. Joined by BuzzFeed Life’s Style Editor Julie Gerstein, we settled in the Billy Reid room, resplendent in deep greens and comfortable leather, and Lauren disappeared to the basement. With the rain streaming down the third floor windows that looked down on Park Avenue, the entire vibe was very Edith Wharton meets Bon Iver. “It’s like we’re play-acting,” Julie said, “we’re living these weird aristocratic British lives, waiting at 'The Club,' but it’s fake. I mean, if you really live like that, you don’t go to Trunk Club.”

Twenty minutes later, Lauren returned with what looked like a drink cart, only it was piled with expensive items of clothing. “Is there anything here that would make you vomit if you try it on?”

Jenna went into the artfully concealed changing space in the corner of the room, where she tried on a series of Theory brand shirts, balked at a pair of khakis, fell in love with a soft, boxy sweatshirt, and tried valiantly to make Lauren understand that she didn’t want to size down so that a shirt would fit her snugly. “I don’t fault them for this,” Jenna told me afterward. “The thing that people don’t understand about butch shopping is that I don't want my figure to show.” She eventually settled on two shirts and the beloved sweatshirt; a pair of Wolverine boots didn’t come in men’s sizes small enough for Jenna’s feet.

As we walked to the subway, we debriefed. “I didn’t feel like they were actually listening to Jenna,” Julie said. “They’re used to listening to men who don’t know what they want, and then just barreling through, telling them, ‘This is what looks good on you.’”

A month after the fact, however, Jenna remains pleased. “It really worked. Having these hot girls telling me that I looked cute made it so that I never even looked at the price tags. I mean, I spent $600 on two shirts and a sweatshirt — that’s ridiculous!”

Both shirts were tailored, free of charge, by a seamstress who measured Jenna on site; later that week, they arrived via messenger at Jenna’s desk. Today, Jenna’s unsure as to whether or not she’ll go back. She’s picky, but she hates shopping, especially when she’s repeatedly directed to the women’s section of a store. The “across-the-board old brothel feel” of the Trunk Club left a bad taste with all of us. But as Jenna admitted, “these are the best shirts I’ve ever owned,” she told me. “And I only want to wear them.”


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