Inside the Early Days of J.Crew: Before Jenna Lyons or Olympia Gayot, There Was Emily Cinader

By Maggie Bullock

When you think of J.Crew, you probably picture Jenna Lyons, the larger-than-life high-fashion persona whose image became synonymous with the brand—if you are a person who has bothered to give the matter of J.Crew's identity any thought, that is. Six years after departing the role, Lyons's image will soon loom even larger as a member of the revamped cast of The Real Housewives of New York City. The generation currently coming of shopping age might solely associate it with its current head of women's design, millennial social media darling Olympia Gayot. But the original human embodiment of J.Crew—though she will surely be uncomfortable to see it put in these terms—was a woman whom even constant J.Crew shoppers have never heard of. Today, she lives deep under the radar at her minimalist Connecticut manse, married to a cofounder of Nantucket Nectars and going by her married name, Emily Scott. But at the dawn of J.Crew, she was Emily Cinader.

There was no "daddy's little girl" about Emily. In January 1983, when she first walked into the offices of the fledgling catalog company her father, Arthur Cinader, had just founded, Emily was 21, a month out of college, completely green. The first J.Crew catalog had just shipped out to 10,000 would-be preps that month. Within its first week, the new bank of telephone operators at the company headquarters in Garfield, New Jersey, found themselves inundated. The customer response was "astounding," an early marketing head told me.

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The operation Emily walked into was all-hands-on-deck, too small to have anything like departments for a newbie to work her way up through. She didn't flounce in with a sense of ownership, but she was no mere assistant, either. Emily was innately discerning, had an eye for style, a hand for quality, an instinct—at a time when the company identity was still wet clay—for what "was" and "wasn't" J.Crew. And she was more than willing to speak her mind. Some describe this quality appreciatively. Others, not so much. Young Emily was either very smart, with every reason to be as confident as she appeared, or boldly entitled, with no one to stand in her way. "She presumed herself a leader of rank," recalls an early executive, "and she took it, was good at it, and it was never challenged."

This new brand, which had been in the works for some two years before the catalog launched, was not anybody's passion project. It was not driven by its founder's particular love for the Ivy League look. Emily's father had inherited from his father a profitable downmarket mail-order company, Popular Club Plan. Arthur had grown the family firm to a size that was likely beyond his dad's wildest dreams, but he knew the company was never going to crack the big leagues. This new offshoot, J.Crew, was a calculated bid at an emerging market: the collegiate prep, whose ilk was driving early ’80s pop culture—kids who dug Ralph Lauren's hit look but couldn't quite swing Lauren's price point.

Debuting as a watered-down Ralph Lauren served its purpose. Just by striking upon "affordable prep" at the right time, J.Crew struck a small tendril of nerve fiber in the culture and established a crucial genetic code: clean-cut, sporty, up-tempo "American" style. While industry wisdom dictated that a brand-new catalog from a company no one had ever heard of had to be prepared to spend two and a half years in the red, J.Crew broke even within roughly 18 months. By 1984 it was a start-up galloping ahead. But aesthetically, the early J.Crew catalog—version 1.0, if you will—wasn't all that different from Lands’ End, the Prairie Home Companion of catalogs. The cute couples J.Crew featured were as wistful as those on the cover of romance novels. Playful shoots of models horsing around on the dock of some collegiate boathouse (because: crew) had a whiff of fromage. J.Crew 1.0 was still leagues away from the catalog that would, a few years hence, become a cultural phenomenon, even an identity—"so J.Crew." That one—the J.Crew for which early fans still harbor intense nostalgia—was 2.0: Emily's J.Crew.

To her new colleagues, all-American youth was a demo, a promising target audience. But to Emily, it was her world.

Officially, what Emily brought to the table in 1983 was a freshly minted marketing degree from the University of Denver. But she had something more ephemeral too, something most of her father's early hires sorely lacked: firsthand knowledge of the young, outdoorsy, preppy life that J.Crew aimed to embody. To most of her new colleagues, all-American youth was primarily a demo, a promising target audience. But to Emily, this was no focus-grouped "lifestyle." It was her own generation. To a degree, her world.

The night Tierney Gifford Horne met Emily, in 1984, the two women were officially on a double date in a Manhattan hot spot. But they paid their dates no mind. Instead, Emily turned the evening into a fact-finding mission. She seemed to want to know everything about Horne's job as a fashion assistant at Vogue. How did the shoots work? How was the styling put together?

Horne was fascinated by Emily and told her everything, but she never guessed what Emily had in mind. She was stunned when, bright and early the next morning, Emily called her at the magazine: Would Horne come work for J.Crew? Poaching from Vogue, period, took chutzpah. Attempting it at a time when "high" and "low" fashion did not mix and catalog brands were strictly steerage class—sorry, J.Who? Well, that gives you a sense of the scope of Emily's ambitions. When Horne told her magazine colleagues about the job offer, they practically put out an APB: You don't leave Vogue for a start-up…catalog…in New Jersey. Was she nuts?

But there was something about Emily. It was partially her beauty: She was a classic Ali MacGraw type. Tall, slim, athletic, with ramrod-straight posture; espresso-dark hair that—even then, at the height of the White Rain big-hair era—was cut in a sleek chin-length bob; and skin that appeared perpetually fresh-scrubbed. The kind of woman who looks stunning in a plain men's button-down shirt. But it was more than that. To Horne, who was just a few years her junior, Emily seemed so adult. She had a stillness, a formality. A complete lack of feminine affectation. It was hard to imagine something as frivolous as a giggle escaping her lips. So there was all that. And then there was J.Crew itself, this intriguing blank slate. Horne said yes.

But when she arrived for her first day of work, fresh from the see-and-be-seen offices of Condé Nast, the warnings of her Vogue sisters rang in her head: Seriously, was she nuts? In its former life, the Popular Club Plan building in Garfield had been a Two Guys discount store. Picture a low-rent Sears: a squat, flat, beige box mired in acres of flat black parking lot. In the front of its fluorescent-lit space, wide as a bowling alley, sat row after row of women in polyester slacks taking payments and orders for Popular Club Plan. Way back in a corner sat the tiny operation that was J.Crew.

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It wasn't just the environs: At first, Horne wasn't sure what she’d been brought here to do. Lots of people who later came to work at J.Crew did so for the very reason Horne just had—largely because there was something about Emily. I spoke with dozens of people who had been hired by her and asked each: What was her vision, exactly? What did she tell you she wanted to do? Most couldn't quite say. She had a sixth sense for people who got it and aggressively pursued talent. Horne was one of many who noted that Emily "saw something in me that I did not see in myself." And once she brought in a new hire, the "right" ones somehow discerned the vision, got on board, and served Emily loyally. The "wrong" ones found themselves spit out a rapidly revolving door.

In fact, what Emily wanted was to make a catalog that didn't feel like a catalog. One with images as beautiful as those in fashion magazines, images that could breathe fantasy into everyday basic clothes. And somehow Emily had divined, over a double date, that Horne, at 20, came equipped with an internal slideshow full of exactly the kind of images that would take J.Crew in that direction. When I first spoke with Horne, she told me about childhood summers spent in the Long Island beach town of Amagansett, at a time when the Hamptons were not yet the Hamptons. Some mornings, her parents would wake up the children at 5 a.m., grab fishing poles and a frying pan, and head to the beach to catch fresh snapper. They’d fry it up on the spot, with eggs, and breakfast in their swimsuits.

When she first described this scene, it sounded so cinematic, I figured it had to be partially manufactured, or at the very least gilded. But the next day she emailed a scan of a white-edged family photo with "1966" scrawled on one corner in Sharpie: a family of five, perched on a rock outcropping before an expanse of deep-blue water. A crisp white sail juts up in the background. In the foreground: two slim parents, three kids, all dressed in shades of madras, with a silver frying pan glinting on a portable barbecue at their feet.

This was exactly the slice of Americana that would soon underpin J.Crew: images that wafted happiness and freedom but also—gently, and without spritzing anybody straight in the face with it—privilege. J.Crew was not the first to pioneer what would soon be called "lifestyle photography." Far from it. By the time J.Crew rolled around, Lauren had already changed the game, with lavish campaigns that depicted his Town & Country garb in situ: on the yachts, golf greens, and sun-dappled verandas upon which the East Coast elite who inspired the look might lounge. These ads papered dorm-room walls. People knew Lauren's models’ names: They wondered whether Lauren's Adonis, Burton "Buzzy" Kerbox, and the aquamarine-eyed patrician-looking Jane Gill were married in real life.

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But it's also true that the freshness of the Ralph Lauren look—so new when it took off in the late ’70s—had begun to rub off. Once that happened, you had to admit, his models did look a little morose. They wore Amelia Earhart–style goggles behind the wheel of their vintage Rolls, but the car was always in park. Why weren't they having any fun? This made for an ideal jumping-off point for J.Crew. There was space for a brand that was not just more affordable, but also more fun, more welcoming. More real.

With J.Crew growing exponentially, the shoestring-budget days of its earliest catalogs—loading a camper van with models and assistants and driving down to the UPenn boathouse—were done. Emily okayed shoots in San Francisco, Newport, Harbor Island. By 1985, when photographer Kurt Markus released After Barbed Wire: Cowboys of Our Time, featuring his black-and-white shots of cowpokes in Nevada and Texas, all Horne had to do was bring the book to Emily: We have to do this. Done.

On a standard catalog shoot, one day might yield a total of eight shots—maybe 10 if you were fast. To eke out more, Horne began styling a whole group of models in layers they could peel off as the day went on. "I’d put on a T-shirt, then a polo shirt, then a chambray, then a jacket," she says. "I’d layer the shit out of everybody, and then we’d give them a task: Okay, make pancakes over an open fire. So there you’ve got your jacket photo." The heavily layered ’80s J.Crew look that became both revered and, eventually, joked about—on non-waifs, four shirts was not the most flattering look—started out as a practicality: fewer outfit changes. Throw off the jacket, on to the next. Horne and her team made the clothes look lived in: They tossed fresh-pressed samples in the wash—sometimes repeatedly—until they looked properly aged. Dunked the belts in water, stomped the boots in puddles. Horne scoured prop houses and rental companies for the perfectly seasoned station wagon, a gross of surfboards, a litter of puppies, and all the flotsam and jetsam of the "having it" life: dainty tea sets, Adirondack chairs, backgammon boards, stacks of Western blankets. She borrowed vintage luggage from T. Anthony, antique watches from Upper East Side jewelers. Shooting things that weren't for sale? This was how magazines worked—not catalogs.

Their other secret: motion. J.Crew models ice-skated in the Adirondacks. Picnicked in the Hamptons. Skied in Deer Valley. 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. All that activity kept them from looking like "catalog people," those cardboard cutouts who existed solely to sell you things. If a model looked stiff, well, throw her on a bike. Hand her a picnic basket. Assign her a boyfriend with whom to play an endlessly thrilling game of tag. Give the boyfriend some shaving cream and a razor. This guy is shaving…on the beach? In his swim trunks? Just go with it.

The litmus test of a great J.Crew picture was: Does it feel real? Could it pass for a snapshot?

"They had this incredible technique, which I absolutely loved," says photographer Tierney Gearon. Her first J.Crew shoot, in the early days of her career, was in St. Barts, with a group of 10 or 15 models. Gearon prefers to work like a film director: "I create a lot of chaos, so the models aren't really paying attention to the camera," she says, and to her amazement, "that's just how J.Crew was working…huge crews, big productions, like a film scene. And it was all about feeling good."

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Back at the office, the litmus test of a great J.Crew picture was: Does it feel real? Could it pass for a snapshot? By the ’90s, this basic rule—no fakery—would be honed to a fine art. One catalog editor I spoke with recalled reviewing the art from each new shoot as a sort of game. The staff would gather in a dark, tiny photo-editing room, sitting on the floor or perched on Formica countertops, as the photo editor clicked through a slideshow (art was still shot on film and reviewed as slides). "We’d all call out: ‘Fake smile!’ ‘Too model-y!’ " says the editor. Or, most damning: "Tee-hee!" This called out cliché hand-over-mouth giggles. J.Crew girls didn't tee-hee. They laughed.

Of course these noncatalog models needed clothes to sell. Let's rewind back to 1984. For its first couple of years, J.Crew had no design team. Merchants ordered mostly existing standards from private-label manufacturers, customized the color or maybe the buttons, and slapped a J.Crew label on them (nothing to sniff at: This was standard operating procedure for many smaller companies.) Emily elevated the product range as best she could, mostly by bringing in things to copy—sometimes as an outright knockoff, more often to match a hue or mimic a detail. Emily's finds would be shipped off to a faraway factory and return as J.Crew product. But the copycat game can get dicey. One early designer recalled that Emily was eventually banned from Ralph Lauren's Manhattan store: They figured out exactly what she was up to there. (Emily flatly denies having been banned.) Another early staffer recalls an inspo trip to Barneys: The woman filled her arms with several thousand dollars’ worth of men's zillion-ply cashmere sweaters, carried them up to the register, and handed over her corporate card. The company name on it read "Popular Services, Inc."

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The salesperson did a double take, from the card back to the fresh-faced woman wielding it: "What is…Popular Services?"

"Oh, it's an escort service," blurted the staffer, surprising even herself. "I’m doing the Christmas shopping."

J.Crew had always planned on hiring its own design team once the company got its sea legs. Maybe this was a sign the time had come?

In 1985, Emily hired designer Linda Snyder, installed her in an office right next to her own, and tasked her with setting up the company's first sample room, ordering sewing machines, steamers, pattern tables, dress forms. But Snyder couldn't wait for these supplies to arrive. One Saturday morning she came in to work, along with her assistant from her former job. Snyder brought her own sewing machine, a pair of sawhorses borrowed from her dad, and a drill. The two women unscrewed the hinges on a stockroom door, set it up on the sawhorses to make a cutting table, and started marking a pattern. By the end of the day, she says, "we had made J.Crew's first proprietary sample."

Little by little, a real design team began to take root. At a cocktail party, Horne spotted a dapper young Southerner named Sid Mashburn. Mashburn was the 24-year-old husband of Ann Mashburn, a chic friend from Horne's Vogue days; in Horne's estimation, he possessed immaculate men's style: J.Press Oxford-cloth shirts, sharp khakis. "My filter was always, would my dad wear it? Or would I date a guy who would wear it?" she says. Soon, designer Claire McDougald was hired to develop knits. Lisa Anastasi made the leap from Ralph Lauren to oversee sweaters. The little design team commuted to Garfield every morning the way city kids get to summer camp: A company van would pick them up on a corner in Manhattan and deposit them in New Jersey. This arrangement, though deeply unstylish, had its upsides: no late nights. If you missed the bus when it came back at the end of the day, you were screwed. (The exception: Emily and Horne often left the office at 11 p.m., driving back to the city in Emily's serviceable, secondhand Volkswagen Scirocco.) Not one of them was over the age of 27, and most had only a few years’ experience—some barely any at all.

This core team churned out a handful of designs that, for a certain generation of believers, still define J.Crew. The thinking behind these garments was not grand or conceptual but deeply pragmatic: These were things the designers longed for in their own closets. "The kind of items that you go out shopping and expect to find but never can," recalls Horne. "They don't quite exist."

You never knew where you were going to stumble on that one perfect thing. Horne remembers walking into the office one day when Emily stopped her in her tracks. "Let me feel your pants," she commanded. They were army-navy pants, but better, from the French company Chevignon. It had taken Horne years to properly break these pants in, achieving a hand feel that, to Emily, was the holy grail. "This is what we have to do," Emily said. As Horne tells it, she handed over her favorite pants, and Emily took out a big pair of shears and sliced off a piece of the fabric; it would be sent to a factory that would replicate the wash. Horne stood there, mouth hanging open. But what was she going to do, tell Emily no? That did not happen.

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Some of J.Crew's greatest hits were relatively subtle improvements on existing items from the canon. Carhartt had its classic Engineer Sack Coat; L.L.Bean had its Barn Coat. Both bore a strong resemblance to J.Crew's Barn Jacket. To design the original, Mashburn inspected an armful of vintage hunting and field jackets and devised a drop-shoulder shape that was appropriately ’80s-boxy, added a plaid flannel lining, and sourced a canvas that was a bit more forgiving than the stiff stuff real hunting jackets were made of. The end product looked like something that had been hanging in a family cabin for decades.

The beloved J.Crew anorak was based on one of Arthur Cinader's old sailing jackets, a pullover style Emily remembered him wearing when she was a kid. The rollneck sweater—a multimillion-dollar item and, to my mind at least, the brand's most iconic—was also Emily's idea, inspired by an old woolen pullover that an ex-boyfriend had inherited from his grandfather. It was so well-worn, it was unraveling at the neck. "There aren't a lot of ways to reinvent the sweater," says knitwear designer Anastasi, but the rollneck did just that—if quietly. It was made without the ribbed trim that usually finishes the hem and neck of a sweater, which allowed the edges to roll up naturally. The J.Crew rollneck was initially a men's sweater, but as the popular girls at private schools everywhere would soon discover, this made it alluringly oversized, just right for pulling over one's hands on a chilly day.

The first time Emily was certain J.Crew 2.0—her J.Crew—was a bona fide hit was because of a photo of Jane Gill—yes, the star of countless Ralph Lauren campaigns.

In the photo Gill wears nothing more elaborate than a T-shirt in palest pink. Her smile is partially shaded by a wide Stetson, and of course there's a tiny Jack Russell nestled in her arms. It's a pretty picture, but no more so than a thousand other J.Crew pictures. So maybe Gill had a special power. Or maybe the formula they’d been tinkering with—aspirational, relatable, comfortable, American—had finally struck gold. Whatever the reason, that photo did what today we would call "breaking the internet." Emily had gone into the season betting big on the T-shirt style Gill was wearing, ordering 5,000 of them—which, for J.Crew, was a huge number. Eighty thousand orders poured in. J.Crew went into overdrive; someone was dispatched on a plane to a factory: More, now!

In the years to come, Emily's J.Crew would morph into version 3.0, then 4.0—moving with the times, as any successful retailer must, but also with Emily herself. When Emily was in her postcollege phase, J.Crew churned out chinos and sweaters; as she matured, so did J.Crew, staking its claim on the 9-to-5 wardrobe. And when, in a twist nobody saw coming, Emily headed to Hollywood, J.Crew did too—albeit in its own tastefully subdued, East Coast way, naturally. It was Bruce Willis who talked Emily into making boxer briefs. Chris O’Donnell told her J.Crew ought to make a tuxedo. (They did.) When Dechen Thurman modeled for the catalog—barefoot, in a red union suit, on a snowy dock floating on an ice-cold lake—J.Crew had a car standing by, ready to whisk him off to the Academy Awards to witness the Oscar moment of big sister Uma—another new Emily friend. Back in the company's whitewashed Chelsea loft space (by the dawn of the ’90s, they had upgraded to more suitable digs), Julia Roberts dropped by one day to say hi. She happened to show up on a day there was a fire drill. She was very nice about it.

What the hell was going on here? It was fairly simple, really: Emily was now half of a Hollywood/fashion power couple. In 1991 she wed her first husband, producer Cary Woods. He would have a hand in some of the edgiest, most zeitgeist-y fare of the decade: Harmony Korine and Larry Clark's raw NYC skate-rat flick, Kids; horror juggernaut Scream; Vince Vaughn and Jon Favreau's star-making spin in Swingers. As far as anyone back in J.Crew's New York headquarters—which, by 1991, included a promising new hire, young Parsons grad Jenna Lyons—could tell, their buttoned-up Emily was hanging behind the scenes in a new milieu and sprinkling valuable fairy dust on the brand. Emily never quite seemed to find her tribe in New York, perhaps because, from the age of 21, she’d been up to her ears in the running of J.Crew. But now she was attending screenings of the Woods-produced football movie Rudy at the Clinton White House. Occasionally, she let slip—in a way that didn't always seem inadvertent—that she’d been at Brad Pitt's pool that weekend.

To the J.Crew originators who had populated Emily's early photo and design teams, who for years humbly boarded a van to get to work and toiled under the fluorescent lights of Popular Club Plan's former-appliance-store offices—people for whom, to put it mildly, working at J.Crew had been anything but glamorous—watching their little catalog company become vaguely…hip? Mind-blowing.

But then, these people would not have put anything past Emily. Today they look back at Emily through a lens informed by the 2020s—this woman who was so young, with no prior experience, and in a rare position of authority. If she were building J.Crew today, Emily would indubitably have been saddled with that albatross girlboss. For years, as J.Crew doubled and then tripled in size, Emily's team—who, agewise, at least, were her peers—saw a woman supremely sure of herself and of her decisions. Who appeared undaunted, tireless. Who, yes, could be condescending and brusque in her delivery; who was strict, hyperparticular, and suffered no fools. But to many of the core team that stuck with her for years, Emily's prickliness was not just a cost of doing business at J.Crew, it was a key ingredient in the brand's secret sauce: Emily's relentless eagle eye for every detail was the force that kept a brand that sold "basics" from tumbling into the pit of blah. Emily never allowed this team to see the pressure she was under or its possible toll on her. (Indeed, Emily did not allow them to see much of anything: From day one, her interior life was a mystery to one and all.) But sometimes they could feel it. When Emily was on set and the models took a break, you could almost hear her mentally calculating the dollars and cents of every lost minute—ka-ching, ka-ching—waiting for them to get back to work. This was not particularly conducive to the happy-go-lucky "realness" J.Crew demanded from its photographers.

Once, an elaborate shoot was planned at a ranch in Jackson Hole. They hauled an army of models, the photographer, stylists, and assistants out West, but somewhere along the way, a connecting flight never arrived. They had to rent a U-Haul, load in clothes, props, and lighting and photography equipment, and drive the rest of the way. The crew didn't get to the ranch until 8 a.m. the following day, bleary-eyed and desperate for sleep. But when they phoned New York to check in, Emily's orders were unequivocal: Get to work.

From the book The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew by Maggie Bullock. Copyright © 2023 by Maggie Bullock. Excerpted by permission of Dey Street Books, an imprint of HarperCollins Publishers.

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