I didn’t always want to work in a store. Few people do. I wasn’t trying to break into the fashion world or even hoping for a discount. But it was 2009. I was going to college in New York City in the middle of a global financial crisis and job opportunities were scarce. I would have worked any job to stay in New York, and thankfully, I had just the right combination of eager pluck and menswear enthusiasm to be employable. Fourteen years later, I’m still doing it.
My first job was a good one. A friend who knew I was looking to hang around the city for the summer recommended that I interview where she worked, the J.Crew at the South Street Seaport. It was the brand’s original location—and a fitting one considering the melange of urban sophistication and nautical aspirations that defined its early catalogs. I was at the company for what Derek Guy—a.k.a. Menswear Guy—called “Menswear’s Last Big Moment”: the 2010 Fall/Winter J.Crew presentation at Milk Studios. It was “the last time we all cared about one affordable and accessible thing,” Guy once wrote on his blog. Around that time, the brand was opening its first Men’s Shops—including the infamous Liquor Store in Tribeca—conceived and designed by Partners and Spade, Andy Spade and Anthony Sperduti’s branding studio.
I loved my job at the Seaport, but I longed to work at the flagship Men’s Shop at 484 Broadway. Not because of the Fellini posters on the wall or the more esoteric third-party offerings from heritage brands like Russell Moccasin and Japanese labels like Anatomica, but because everyone there—staff and customers alike—looked so effortlessly cool. Personalities from the New York menswear scene, like Joshua Kissi of Street Etiquette and Chris Echevarria of Blackstock & Weber, would pass through the store on the regular. When I caught up recently with the inaugural store director, who asked to go unnamed, he told me he recruited many early staffers from internet forums like Niketalk, Styleforum, and Superfuture. It was important to him that he fill the store with people who were passionate about clothes and cared deeply about their own personal style.
In his negotiations with Mickey Drexler, then CEO for the brand, the director asked that the shop be exempt from the somewhat dry uniforms required at other locations—dark denim and a blazer or chinos and a tie. Then, entirely of his own accord, he took things a step further: Every morning before opening, the store director would line up the staff and critique what they were wearing. Eventually, he was told by HR that there were softer ways to foster an elevated personal appearance standard. But by then it didn’t matter, because he had already created a culture where great fits were celebrated—and lesser ones were roasted, gently. By the time I finally landed a Men’s Shop position in 2012, photographers from Japanese magazines like Free & Easy, Lightning, and Popeye would occasionally drop in to photograph the staff unannounced. If you weren’t already dressing to impress your peers or your customers, you especially didn’t want to fumble the opportunity to be glorified and captioned by inscrutable text in a foreign menswear bible.
All of the most interesting—and sometimes outlandish—people I’ve ever known are current or former coworkers. Most people who work in stores are doing something else and they need the odd hours and weekdays off to get these things done. A guy who worked on the shoe floor at Bloomingdale’s forced CDs of songs from musicals he’d composed on colleagues and customers. The cover featured two photos of him: one seated at the piano looking pensive in a black T-shirt, and another lying across the piano, smiling in a black suit. I’ve worked with vintage sellers who got famous for street racks, countless musicians, one of Evander Holyfield’s many sons, an actor who got fired for sneaking into the fitting room to practice lines, and a girl who married the son of a famous mid-century painter and posted relentlessly about her newfound wealth on social media.
To sell is to converse. It begins with a well-timed approach. No one likes to be blindsided by an overenthusiastic salesperson. Take too long, however, and you’ll have to overcome whatever notions of the store have already rooted themselves in the customer’s mind. Then, it’s like being a good host at a dinner party. Keep your house tidy and ask more questions than you answer. Thankfully, there’s time to practice. Throughout the week, you’ll face long quiet stretches and the only diversion is meandering conversations with your coworkers: the ideal ratio of rise to leg opening on a pair of jeans; the highlights of the discography of the punishing experimental rock band Swans. We take this useless knowledge and use it to contextualize clothing for men who don’t give it enough thought.
During my onboarding at a major department store, the corporate trainer drew a big circle and then covered the rest of the board with a series of smaller circles. Ninety percent of your business will come from 10% of your customers, she told us. It felt like a scene from Glengarry Glen Ross. At this very department store, there was a program for these top-end customers that came with a host of perks that ranged from a private customer service hotline to 24/7 building access.
A coworker of mine once stayed at the store until 2 a.m. babysitting a rich couple’s children, ordering them food, and pouring champagne while they shopped. She walked them from floor to floor, calling the engineering team who had to switch lights on and off, acting a bit like a New York realtor who is always a step or two ahead of her prospective buyers to anticipate any ugly details. In this case, she was wary of the other teams still working late into the night: visual merchandisers from different vendors putting ads into backlit glass cases and creating sculptural displays with loud power tools; a night crew roaming the building to pick items for online orders; another team engaging in the Sisyphean task of returning items misplaced amongst the 13 or so floors of retail. This coworker worked in one specific area of this giant store, so she wasn’t familiar with the labyrinthine stock rooms she had to navigate with her iPhone light, always aware of the amount of time her customers were alone. Ultimately, the couple spent somewhere between $10,000 to $15,000, a light shopping trip ahead of a lengthy vacation.
The more luxurious the product, the more insane the customer. At a high-end consignment shop in the Upper East Side, just a stone’s throw from Jeffrey Epstein’s former residence, I was asked twice if I could rush a transaction as the customer’s helicopter was leaving imminently. A few years ago, over several appointments, a man sold every watch he owned to us. A wild but garish collection that included a Rolex Yachtmaster, a Royal Oak, a few Richard Milles—lots of skeleton movements, precious metals, and wild complications. Not a single timepiece under 42mm. Once we developed a familiarity, I asked him what motivated him to sell everything. I expected to hear about the opportunistic watch market, a contribution to some sort of legacy fund, maybe a potential property purchase. Instead, he responded that he realized they all tell time. I mined that simple response for all the depth that I’m still not sure was actually intended.
On a more sour note, a newlywed couple once came in intending to sell an Hermès bag as a down payment on a new house. The bag had been given to the groom’s mother years earlier as reimbursement for a substantial loan and then was passed on to the couple as a wedding gift. Unfortunately, it was deemed a fake, although a rather convincing one. The man did not take the news well. Not only was it an unfortunate setback on the prospect of a new chapter but a personal affront to his family’s reputation. I don’t take any schadenfreude from a dream deferred, but I wonder: Should any handbag really be selling for 10% of a two-bedroom home in an expensive zip code?
A few things you, as the consumer, should be aware of. A small list of retail commandments:
Never ask for a discount. If there’s one to give, it will be granted. A retail store is not a bazaar.
The staff know the product. They’ve probably sat with the merchants and designers who made the product and tried everything on themselves. Then they’ve seen it drape on every possible body type. They take pride in their work and you are their canvas. Trust their opinion and be open to suggestions. No one wants to deal with a big return.
Don’t ask nerd questions you already know the answer to. No one cares. The most stylish people I know could care less about a selvedge seam or a loop wheel sweatshirt.
You wouldn’t visit someone’s house and expect to not participate in conversation. If someone asks you a general question of well being, do not, under any circumstances, respond with “I’m just looking.”
In an interview for my first retail management job, the hiring manager asked me why I liked clothes. It’s a good question that I still ask when I interview people. My answer was simple: I wanted to look like someone, specifically the musicians I idolized. No one in my family or in my daily life wore their clothes. Clothing was a utility to them. While I admit there is an attitude and a personal style in a rock musician that perhaps, as a 13-year-old child, I did not fully inhabit, the clothes of the time were also bad. It was 2002 and we walked into Macy’s with a picture from the back of my Essential Clash CD’s liner notes. In the picture, I’m pretty sure all the band members are wearing Levi's 505’s from the ’70s, but nothing even remotely similar existed in the denim area. The staff were far from helpful and while my mom was onto something by describing the fit as a cowboy bootcut, the description didn’t resonate with the staff. We left empty handed and I felt further away from another life than I already was in my suburban New Jersey middle school existence.
My core responsibility is to make people feel comfortable enough to tell me what they want and then connect them to a product that makes sense. I take it seriously. The people who love clothes and follow the trade like sport don’t need my help—although I love shooting the breeze with them. It’s the men who are a little embarrassed to admit that somewhere along the way they fell out of step with the zeitgeist that I like to help the most. While the perfect pants fit is a shifting goal post, sometimes as varied as the weather and the cultural touchstones on my mental moodboard have changed quite a bit, I never want anyone to feel like a chubby kid with a picture of Joe Strummer in the middle of Macy’s.