Old J.Crew sold preppy, privileged dreams as much as loafers and button-downs. A new book breaks down its cultural effect

Sometime in the early ’90s, when I was a teenager, I spent a spring weekend in New York City with my sister and my dad. I have no recollection of where we stayed or what we did on that trip, but I remember what I bought: a madras bucket hat from J.Crew’s first and at the time only store.

The company started as a mail-order retailer in 1983 and its catalogue would regularly land in my parents’ mailbox in midtown Toronto. It was a bible of American leisure and broken-in cool and I studied its pages with extreme focus as if I were French chemist Louis Pasteur peering through a compound microscope. Except what I was examining was a pontoon anorak in “parsley sprig.”

I can still remember the euphoria (Crewphoria?) I felt upon entering this high-ceilinged cathedral of prep in Manhattan’s South Street Seaport, overwhelmed by a kaleidoscope of roll-necks and henley tees, leisure set to seersucker and broadcloth. The staff looked as if they’d just left their lifeguard tower in the Hamptons to fold some chambray. When I returned to Toronto, sporting my new hat, I felt temporarily cooler, more playful and insouciant than I was — the sort of person who didn’t have insomnia and could join in a spontaneous round of ultimate Frisbee (and enjoy it).

I went to a high school populated with girls who looked spectacular in cut-off jean shorts and oversized J.Crew roll-necks in shades of mist or pine. Their fashionable ski-jump noses were sprayed with freckles, souvenirs of summers spent water-skiing or sailing with their floppy-haired boyfriends. There is, of course, a rare intensity to adolescent longing. I pined for those J.Crew garments as ardently as I longed for the other things I didn’t have: the cute boyfriends, the facility with sport, the self-possession.

Maggie Bullock, author of the new book “The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew,” remembers her seminal J.Crew moment clearly too. She wore a roll-neck to the dining hall of her Long Island boarding school, where she had arrived from North Carolina as an outsider. “I’m sure no one else noticed, but to me that sweater felt like a password, a secret handshake. In it, I felt as if my rough edges — my outsider’s accent — were ground down. I felt like one of them.” Adding to the sweater’s cachet, she had borrowed it from a boy named (of course) Andy. “I had crossed over into cool-girl territory,” Bullock tells me. “Later in life you discover that nobody was comfortable, everybody was riddled with anxiety, everybody was stewing, but to the naked eye they looked like they were having a blast and perfectly at ease.”

This fantasy of ease and belonging is at the core of J.Crew’s mystique. “The clothes themselves can be pretty plain but they’re put together and situated into the snow globe of a lifestyle — and you just want all of it,” says Bullock. “The Kingdom of Prep” breaks down how it was done — it’s a fashion-business story that has the sweep and propulsive pace of cinema, cast with big, colourfully-flawed characters and rife with stakes both financial and emotional.

Other catalogues of the time, like L.L. Bean’s, focused on the garments, but J.Crew peddled a vision of Americans at play, all movie-esque montages of leisure. The images were cleverly staged to pass as family snapshots: Coltish models rode their vintage bikes past cranberry bogs in Nantucket; they gambolled through wildflower meadows with blond dogs and matching children.

Everyone in the pages looked profoundly comfortable — not just in their Liberty-print popovers but with their family members, with their life choices. The clothes were never tensely starched but slightly crinkled as if by a brisk breeze, their colours slightly faded, as if the garments themselves had just returned from a relaxed weekend scalloping in Maine. Crispness betrayed effort, and effort was for strivers — outsiders.

“You could argue that all of fashion is about the illusion of ease. Even high fashion,” Bullock says. “Carrie Bradshaw can run down cobblestoned streets in Manolos. She tries really hard in what she wears but she wears her clothes with enormous ease.”

In J.Crew’s universe though, the fantasy of leisure was buttoned to one of activity and competence. Ease was not to be confused with languor. It was ease in motion. “J.Crew models ice-skated in the Adirondacks. Picnicked in the Hamptons. Skied in Deer Valley,” writes Bullock in The Kingdom of Prep. “They shimmied up the mast of a sailboat; strapped a Christmas tree to the roof of the family Wagoneer; raced along a train platform, bags in hand, en route from someplace good to someplace even better.”

This helped me unlock my own adolescent fascination with J.Crew. Let’s put it this way: my own vacation snapshots did not look like this. At summer camp, while the other girls were sailing, I sustained an injury on the pottery wheel (it fell on my foot). Reader, I landed in the ER by making a mug.

And, about five years ago, I went to South Florida with my family, and the setting was as fresh as a J.Crew tableau — blond sands, a wind-frilled sea, tall, wild grasses. Then, my son lofted a beach ball into the air and my mom gamely retrieved it from the foliage, where she scratched her cornea on a particularly sharp blade of grass. We ended the day in urgent care. I have more examples than J.Crew has names for cream that prove ease is not part of my family playbook.

Of course, the iconography of ease I fantasized about was just that, a fantasy, at least for most of us. “It wafted happiness and freedom but also — gently, and without spritzing anybody straight in the face with it — privilege,” writes Bullock.

As the forefather of prep Ralph Lauren (born Ralph Lifshitz) famously said: “How can a Jewish kid from the Bronx do preppy clothes? Does it have to do with class and money? It has to do with dreams.” Bullock points out that Calvin Klein too, as well as J.Crew founder Arthur Cinader and Mickey Drexler, its chief executive from 2002 to 2019, were also Jews from the Bronx. “Everybody who shaped the company was an outsider to the world they were trying to portray, partially because the world they were trying to portray doesn’t really exist,” she says. From the barn jacket to the piqué polo, prep is “America’s uniform of belonging.”

There is no ease without struggle, no madras hat without misery. And dreams, like a great button down, will never go out of fashion.