Designer Eveningwear for 2014 from Carolina Herrera, Oscar de la Renta, Michael Kors and Brooks Brothers.

“There was no easier child,” Steven Stipelman’s mother once told him. “I gave you a piece of paper and a pencil. You were gone forever.”

Mama Stipelman assessed her son well; his boyhood passion has never wavered. It took Stipelman from his hometown of Brooklyn, N.Y., to New York’s High School of Music & Art (now named La Guardia, for its founder), the Fashion Institute of Technology and, ultimately, to a storied career in Women’s Wear Daily’s art department. There, as part of a remarkable stable of illustrators that included Kenneth Paul Block, Robert Melendez, Robert Passantino, Kichisaburo Ogawa and others, he defined the visual lexicon of fashion’s paper of record for decades. Today, Stipelman works at his alma mater as a professor of fashion art, teaching illustration and portfolio design to fashion design students, while instilling in them an appreciation of industry history (plenty of Geoffrey Beene and James Galanos).

Stipelman recalls his professional milestones fondly, with a combination of wry humor, resignation at inevitable change and joy at the good fortune he’s had to spend his life surrounded by talent he respects in an industry he loves. While he correctly cites the late Block, who died in 2009, as the undisputed star of WWD’s illustrator roster, he plays down his own status. Yet in the world of fashion illustration within and beyond WWD, Stipelman was, and remains, a super nova.

While Block was renowned and revered across the industry well before the younger upstart Stipelman arrived at WWD in 1965, by the Eighties, Stipelman was no one’s second fiddle, and often the first choice for high-fashion assignments. At the same time, younger editors considered it an honor if art director James Spina or later, Andrew Flynn, paired them with Stipelman for features on more populist markets such as Junior Sportswear or Jeans and Causal Pants. (Yes, WWD dedicated endless special sections to Jeans & Casual Pants.) “I loved that [high-fashion] world, those very serious clothes,” Stipelman says. “But could I draw a swimsuit? Yes.”

Chanel Spring 1991 Couture Collection Advance. Illustrated by Steven Stipelman.

Chanel Spring 1991 Couture Collection Advance. Illustrated by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

He discovered his love of art early and never wavered from  that pursuit, blessed with a mother who encouraged his youthful interest. (His mother had had her own creative inclinations, and studied millinery at Pratt until the Depression changed her plans.) In middle school he found a mentor in his teacher Eleanor Merritt, who encouraged him to apply to Music & Art. He made the trip into Manhattan to take its grueling three-hour entrance exam, and was overwhelmed by the talent of his fellow prospective students: “I had always been the best artist in my class,” he said. But there, among some of the city’s best aspiring artists, he felt “like a local beauty pageant winner going to the Miss Universe pageant where everyone is beautiful.” By his own assessment his test did not go well, and he spent the train ride home crying. The tears proved premature — he was accepted into Music & Art for his sophomore year.

Stipelman considers his time at the high school the most formative years of his life. He focused his studies on painting until taking a fashion course with an extraordinary teacher named Julia Winston. Over the objections of other instructors who considered him a painter at heart, she suggested that he consider Parsons or FIT for college. Winston’s advice won out, and Stipelman opted for FIT.

Perry Ellis Fall 1986 Ready To Wear Advance, Ralph Lauren Fall 1986 Ready to Wear Advance, Calvin Klein Fall 1986 Ready to Wear Advance and Oscar de la Renta Fall 1986 Ready To Wear Advance. Illustrations by Steven Stipelman.

Perry Ellis Fall 1986 Ready To Wear Advance, Ralph Lauren Fall 1986 Ready to Wear Advance, Calvin Klein Fall 1986 Ready to Wear Advance and Oscar de la Renta Fall 1986 Ready To Wear Advance. Illustrations by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

After completing his degree in two years, Stipelman interviewed for two jobs, one sketching ads at Henri Bendel and one at WWD. Here, he interviewed with Rudy Millendorf, the forward-thinking art director who for years oversaw the look of the title and who was viewed as both mentor and legend by those who worked under him. Neither first interview panned out for Stipelman, though he would eventually land a gig at Bendel’s. WWD, however, was “everybody’s dream job.” While Millendorf saw potential in Stipelman’s early portfolio, he told the recent grad that the work “looks like school.” The rejection wasn’t absolute, and he prompted Stipelman to come back in a month after looking at fashion coverage and trying to draw the clothes. When Stipelman returned as directed, Millendorf repeated the advice. All told, it took about a year before Millendorf hired Stipelman, later explaining to him that previously, his work had been “too good for the back of the paper and not ready for the front.”

Stipelman was not yet 21 years old, and suddenly found himself working alongside Block who, according to Stipelman, “literally created Women’s Wear.” (Take that, John Fairchild.) Stipelman had admired Block’s work since high school, when he’d encountered one of the older artist’s ads for Bonwit Teller. “I said, ‘This is the most beautiful thing I ever saw in my life. This is what I want to do,’” he recalled. Inspiration begot intimidation, however, when Stipelman found himself working alongside his early idol. Seeing Block at WWD, Stipelman was tempted to run: “Let me out of there. The last thing I wanted was for this man to come over and see that I exist. And he did.” Block invited his new colleague to lunch, but ultimately, friendship took time; Stipelman noted that their last few years at the publication were their friendliest.

Rudi Gernreich Resort 1967 "Diaper Suit" for Harmon Knitwear. Illustration by Steven Stipelman

Rudi Gernreich Resort 1967 “Diaper Suit” for Harmon Knitwear. Illustration by Steven Stipelman  Fairchild Archive/Illustration by Steven Stipelman

At the time, the Fairchild offices were on East 12th Street off Fifth Avenue. WWD was on the third floor, with the art department in an area in the back, separated from the newsroom. For young reporters new to the company, that artists’ enclave could be an intimidating place, and some felt they endured an unofficial hazing process (marked mostly by a lack of conversation) until earning the respect of the department’s denizens.

Yet far from cutthroat, the artists ultimately proved accessible and collaborative with reporters. (Those who found full favor might be invited for the Friday afternoon Champagne that somehow avoided the notice of the executive side.) Among the artists themselves, Stipelman remembers a friendly, creative environment with very little competition. They all specialized in their own areas and celebrated each other’s victories. Passantino, for instance, “had a great graphic eye. You can give him gloves and get a masterpiece back. You give me gloves and I’m going to see 10 fingers and no fabric.” Melendez, meanwhile, had a wild and vivid imagination: “He could draw an elephant chasing a cockroach wearing tartan pants. I mean, there was nothing he couldn’t draw.” Catherine Clayton Purnell, for years the only woman illustrator on staff, excelled at children’s wear, bridal and anything she could interpret in a highly detailed, whimsical context. “They would never give her a Dior, because that was not her head.”

Stipelman arrived at the moment when the designer likes of Rudi Gernreich and Mary Quant were revolutionizing fashion. “I was the age for the clothes,” he noted, so Millendorf gave him those assignments. But Stipelman showed deftness not only in capturing fashion’s renegade spirit, but its more traditional sensibilities, as well. Though versatile, his core aesthetic was elegant and more impressionistic than literal, lending itself beautifully to the haute and tony ready-to-wear that at the time anchored the fashion world. Millendorf thus started assigning him high fashion work when Block was over-booked.

Stipelman credits senior editors Matilda “Tibby” Taylor and June Weir for being his two biggest, early boosters at the paper, and he adored working with them. “I owe it all to them,” he said. “They would go to Rudy and say, ‘Can I have Stephen for the day?’” John Fairchild, however, remained a distant, imposing presence. Throughout Stipelman’s tenure at WWD, the two never formed a close relationship. “He was with Kenneth, end of story,” Stipelman recalled. That’s not to say that Mr. Fairchild didn’t take notice of Stipelman’s work; Mr. Fairchild took notice of everything at the title he was by then directing. He would communicate his pleasure, and on occasion, displeasure, in three-line notes delivered on blue three-by-five index cards. (Once, when then-editorial director Patrick McCarthy, a John Fairchild protégé, was asked in an interview the origin of the blue-only index cards, his answer was something along the lines of, “I have no idea.”)

Designer Summer 1985 Ready To Wear Advance Supplement. Illustration by Steven Stipelman.

Designer Summer 1985 Ready To Wear Advance Supplement. Illustration by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

Stipelman found himself working on more and more important assignments. He was particularly good at portraiture at a moment when Mr. Fairchild was quite taken with the social set and loved depicting its ladies done up in their designer finery. Often, Stipelman never actually saw the women dressed in the clothes. Instead, he worked from photos for their likenesses, and drew their outfits either from croquis supplied by the houses or even from verbal descriptions. A favorite subject across decades: Jacqueline Kennedy Onassis. One particularly labor-intensive story on Valentino-loving ladies featured a Stipelman illustration of Jackie along with several other women, including her sister in law “Mrs. Edward [Joan] Kennedy,” Babe Paley and Jayne Wrightsman.  

New York Society Ladies in Valentino Couture, Fall 1969. Illustrated by Steven Stipelman.

New York Society Ladies in Valentino Couture, Fall 1969. Illustrated by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

Not every occasion went as swimmingly. In advance of Lynda Bird Johnson’s wedding, Taylor and Weir told Stipelman that they needed a drawing of the first daughter’s bridal gown. The only problem: They had zero information about the frock designed by Geoffrey Beene. According to Stipelman, they set about gathering clues (recent designs, a swatch of fabric rescued from a workroom trash can) to put together a shot in the dark. And they got it all wrong. Fairchild then stepped in, chalking the inaccurate sketch up to the capriciousness of Texans and a change of heart rather than the publication’s mistake. A new sketch would follow, and somehow, based on whatever recon the editors could glean, Stipelman nailed it. (While not the last straw, that incident played into the longtime, zero-contact feud between Beene and WWD. It also resulted in a cause célèbre among the media when WWD was banned from covering the wedding.)

"That Wedding Dress" Lynda Byrd Johnson Wedding Dress deigned by Geoffrey Beene. Illustration by Steven Stipelman.

“That Wedding Dress” Lynda Byrd Johnson Wedding Dress deigned by Geoffrey Beene. Illustration by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

Trips to Paris were equally memorable. Early in his career Stipelman went to the collections in Block’s stead twice (once when Block fell ill, and once when jury duty called). On his first trip, he was scheduled for lunch with Mr. Fairchild at the Ritz Bar. The restaurant originally denied him entry for want of a necktie, but ultimately agreed to let him stay as long as he kept his cloth napkin tied around his neck for the duration of his meal. On that trip, Stipelman covered an event at Maxime’s, drawing Elizabeth Taylor, in town for an event. On a later trip to Paris, Stipelman found himself waylaid by a hangover on the morning of a Dior appointment with Mr. Fairchild, who called the hotel to inquire as to his whereabouts. Stipelman ran out of the hotel stressed and anxious, but ultimately made the appointment. On the way out, Mr. Fairchild asked if he were feeling well, to which he replied, “I think I’m going to throw up.” He then returned to the hotel via taxi, lest the block-long walk prove too daunting in his fragile condition.

Hangover aside, such exposure fueled Stipelman’s interest in fashion history, and he acquired deep knowledge of it. For WWD’s 75th Anniversary issue in 1985, various editors were each assigned to distill a decade, requiring then to go through every single one of its issues, then preserved in a library of “bound volumes.” In deference to time and sanity, fashion editor Etta Froio sent the mostly young staffers to Stipelman for a list of bullet points on which to focus. He delivered, his teaching acumen already apparent.

Over the years, Stipelman started collecting couture pieces; though his acquisitions have slowed, at the time of this interview he was in the running for a 1964 Norman Norell jacket on eBay. Norell is the object of an early fashion memory that still resonates. As a kid, Stipelman happened upon the famous 1960 photo of the designer surrounded by four ultra-glamorous models dressed in his slinky, linear evening gowns. “I almost died,” Stipelman said. He saw his first real-life Norell during his stint at Henri Bendel. Ditto his initial exposure to Galanos, who made “the most gorgeous clothes in the world.” That long-running affinity was later cemented at the Plaza Hotel, during a two-day preview of the designer’s work with Weir. So grateful for the wonders on display that he had the opportunity to draw, he wrote Galanos a thank you note and included a sketch he’d done of the designer. Years later, Stipelman was tickled to see his drawing, framed and on display, at a retrospective of the designer’s work in Philadelphia.

Ossie Clark Fall 1973 Ready To Wear Advance. Illustrated by Steven Stipelman.

Ossie Clark Fall 1973 Ready To Wear Advance. Illustrated by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

Among other high points that ultimately fed his love of fashion, he cited André Courrèges as “the first one who knocked me over — those stovepipe pants.” Yves Saint Laurent’s Gypsy Collection also blew him away. Balenciaga was a favorite, but more a historical than real-time fascination. He considers Perry Ellis “a genius” who introduced a whole new, more casual attitude to tony dressing, clothes that were “just beautiful and not pretentious looking.” More recently, Stipelman applauded Alexander McQueen for his glorious, controlled theatricality. Among designers, he singled out Valentino’s Pierpaolo Piccioli for his mastery of extreme fantasy and real-life ready-to-wear collections “that are some of the most beautiful clothes I’ve seen in my life.”

Overall, however, Stipelman thinks that designers today are disadvantaged relative to those whose work he illustrated over decades at WWD. Then, they had time to develop. “Now what happens? You’ve got one collection [to prove yourself], and you could be fired. How do you create this way? This is insane,” he maintained, and just one of many facets of the industry vulnerable to fashion’s often harsh vicissitudes.

The fate of the fashion illustrator is another. The illustration component of WWD’s art department was disbanded and its artists unceremoniously let go on a single, stark day in the early Nineties. While Stipelman recalled the handling of the layoffs as graceless, he harbors no ill will, calling the move an unfortunate but inevitable result of industrywide change, specifically the victory of photography over hand-drawn art. “The paper turned into something else,” he said. “That’s called life. I mean, one day you don’t wear bustles, one day you don’t wear girdles, one day you don’t wear gloves and hats.”

Valentino's Special Fall 2014 Couture Collection for New York designed by Pierpaolo Piccioli and Maria Grazia Chiuri. Illustration by Steven Stipelman.

Valentino’s Special Fall 2014 Couture Collection for New York designed by Pierpaolo Piccioli and Maria Grazia Chiuri. Illustration by Steven Stipelman.  Fairchild Archive/Illustration by Steven Stipelman

Just as bustles, girdles and hats will never return as staples of the everyday wardrobe (in the age COVID-19, non-winter gloves — who knows?), fashion illustration as a sound career option has ceased to exist, at least relative to what it was when Stipelman opened his portfolio in front of Rudy Millendorf. That said, he sees pockets of possibility, mostly in cosmetics, trend reports and areas “where the clothes are maybe not reality-based.”

Yet such is not the focus of illustration instruction at FIT, where Stipelman has found a fulfilling professional second act in teaching. These days, “we don’t have a fashion illustration major,” he said. “No school does.” Instead, the discipline is now called “fashion art,” and focuses on using illustration to help fashion design students “get their ideas out on paper and build these really beautiful portfolios.”

Stipelman encourages his students to be forward-thinking while respecting the accomplishments of their predecessors. In one class, he requires a project on heritage designers (read: those no longer working), with Beene, Vionnet and Claire McCardell among top examples. He is sometimes bemused at the reverence students show for icons of the past; for example, when he assigns students to select a muse, Audrey Hepburn remains a top choice. And when he shows them Kenneth Paul Block’s work, they react not just with appreciation, but with emotion. “Tears come out of their eyes,” Stipelman said. “These are 18-year-olds, pierced and tattooed — their mouths drop open.”

Stipelman relates to finding that kind of passion in one’s work — although he might take issue with the word “work.” “I never thought I had a job,” he said. “If you asked me now what were your jobs, I would give you my three summer jobs when I was in high school. But working at Henri Bendel was never a job. Teaching is never a job. Women’s Wear was never a job.

“The joy at Women’s Wear, it was the whole atmosphere of the place,” Stipelman continued. “We all couldn’t do what the other one did. I mean, technically, of course, we could if we had to. But we all had our strengths, so there was an electricity. And we were all friends. That was the fabulous part.”