Fashion insider: Jeffrey Kalinsky’s second act

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Jeffrey Kalinsky learned his most valuable lesson as a child in Charleston, South Carolina, while helping out on the sales floor at Bob Ellis, the shoe store that his father owned.

“If you try to sell somebody what you think they want, you’ll never be successful,” Kalinsky says, speaking on Zoom from his West Village home office, a minimalist oasis of neutral tones. “Success will come from selling people what you want them to have.”

Kalinsky, the founder of the iconic Jeffrey boutique chain, has spent his entire life mastering the art of the sale. Immediately after graduating college, he apprenticed on the shoe floor at Bonwit Teller in Philadelphia; then worked as an assistant shoe buyer at Bergdorf Goodman in New York; and moved on the shoe floor of Barneys. He was in his mid-thirties when he set out to put his name on the map — literally — with Jeffrey, his first store opening in Atlanta in 1990. Five years later, Kalinsky brought the retail concept to Manhattan’s Meatpacking district in the form of a 12,000-square-foot shop on far west 14th Street. The store brought in just under $25 million in its first year and, “the second year was even better,” Kalinsky says. By 2018 he succumbed to the siren call of Silicon Valley, opening a Palo Alto outpost.

But, two years and one pandemic outbreak later, Jeffrey folded. Nordstrom, which had bought the business in 2005 and appointed Kalinsky vice president and designer fashion director, shuttered all three locations as part of a larger Covid-19 restructuring in 2020. For many retailers, customer service moved online, and the end of Jeffrey in part represented the end of an era of retail that revolved around high-touch service and familiarity. “Jeffrey represented a kind of tastemaker that has been replaced by red carpet coverage and Instagram,” says journalist Teri Agins, who covered the fashion beat for the Wall Street Journal when Kalinsky launched his mononymous empire. “Shopping at Jeffrey was less overwhelming than going to Barneys. His number one priority was making his customers look good.”

High-end boutiques that offer an intimate alternative to department stores are vanishingly rare (Ikram Goldman’s cult Chicago boutique Ikram might be the last of its ilk). Unlike the influencers and celebrity stylists who have taken on the mantle of fashion curators, and are often compensated by the brands they promote, “Jeffrey knew his customers’ bodies and their insecurities,” says Agins. “Women got hooked, the same way they do with their hair stylists.”

More than a retail destination

The Jeffrey in Manhattan’s Meatpacking District was more than a retail destination. Filled with the work of emerging luxury designers including Alexander McQueen, Céline and Jil Sander, and trafficked by Manhattan’s best dressed (and a fair share of rubberneckers), the store often felt like an art gallery on opening night. Its buzzy reputation inspired a series of Saturday Night Live sketches about the snobs who worked at a shop named “Jeffrey’s” and insulted poorly dressed customers.