On the top floor of a 21-story co-op building on Manhattan’s Lower East Side is a two-bedroom-with-balcony overlooking the East River and Williamsburg Bridge. It’s an enviable perch, which Ellen Weinstein shares with her husband, fellow illustrator David Flaherty and Fritzie, their miniature long-haired dachshund and frequent muse. The space doubles as their studio: Flaherty works from the spare room, while Weinstein creates her illustrations for the New York Times, the Atlantic, Time and the Washington Post, among others, from a desk near the front door. Vintage photographs, postcards and memorabilia serve as inspiration around her small workstation. When she isn’t presiding over the board of directors for the Illustration Conference (ICON8), teaching illustration at the Rhode Island School of Design (RISD) or running workshops in exotic places such as Italy and Mexico, she can be found right there, sketching in her notebooks, filing away pictures or compositing images on her Mac. Unless, that is, she’s working from her second home in Hawaii.

“[David] and I started going out to Maui in 1999. On a whim, we sublet our apartment and went there for five months,” Weinstein recounts on a gray October morning. On that first trip they went as guests of illustrator Adam McCauley, but the next year bought land of their own in the upcountry town of Haiku. A consummate New Yorker—born and raised on the Lower East Side, with brief stints in Brooklyn and Manhattan’s Upper West Side—Weinstein appreciates that she can alternate between the concrete jungle and their island paradise. “I’ve plugged into the Hawaiian culture.

I paddle on an outrigger canoe team when I’m there, and I’ve learned Polynesian chants. It’s great for people like me who can telecommute. I used to tell people when I was out there, but then I realized, clients really don’t want to know you’re working from Hawaii,” she says, laughing.

The sun-drenched lifestyle comes through in her work. As if her sepia-tone source material were also infused with vitamin D, she uses color and natural themes in abundance. She also modified her working process to better suit her laidback environs. “I was working three-dimensionally for a while. I would build these constructions and then spend a lot of time lighting them and shooting them with a 4×5,” she says. “In some ways I still try to recreate that [look], because I like the depth that it provides. But I found that that process was getting a bit cumbersome, so I let that go.”

Combining old—“I have my family photos; my husband is from a big family and I have some of their photos; and over the years friends have given me their family photos too, so I have a pretty extensive archive”—and new—digital pictures she takes with a Nikon COOLPIX or her iPhone—Weinstein blends photography with elements of her own painting and drawing. Her Mac is the last tool she employs, to put all the pieces together. “I can only think analog, so whenever I’m working on something, I’m just immediately making scratches on paper. I start with rough pencil sketches.” She plays with perspective and proportion, often juxtaposing super-flat painted images with more textural, photographic ones. “I like the feel and the look of actual material, and I like to play with what’s real and unreal. Whereas I’m not nostalgic at all, I love playing with it in my work. Mainly I want to create this open space for a metaphor,” she says.

Her faces come from another era or, in some cases, are nonexistent. Take The Cannonball Lady, a surrealistic collage she created for a 2010 show organized by the Italian Teatrio Cultural Association. On a yellowed record sleeve as canvas, she layered painted textural pieces to form a portrait of a redhead, with a graphic of a 1920s-style woman being shot from a cannon where her subject’s face would have been.  “The more specific people get with clothing and with faces and very specific settings, it interrupts that place where somebody can just look at something and project themselves into it,” says Weinstein.

Nonhuman subjects are prevalent too. Fritzie appears on occasion, and the rest of the animal kingdom is well represented. For another New York Times health article, about how aging eyes affect circadian rhythms, her subject is a heavy-lidded rooster sporting pajamas and thick glasses while nursing a cup of coffee under the late-morning sun. “I play with using a lot of animals in my work, but they’re anthropomorphized. It’s just another way of telling a story and getting away from the subject matter, to get away from being literal,” she says.

Fortunately, her imagination has always been allowed to run free. Her parents, union organizers who pursued artistic hobbies, were supportive. “Their jobs were just a way to make money and support the family. They were very encouraging that I do something that I love for a living,” she says. She describes herself as “pretty nerdy as a kid,” a quality that helped her get accepted to The Bronx High School of Science and the High School of Art and Design. She chose the latter and recalls, “Being able to go to an art high school was a great experience, to be accepted for yourself as an adolescent.”

Growing up in the city she was exposed to world-class art museums, but it was the art she found on the street, in the form of advertising posters by the likes of Milton Glaser and Ivan Chermayeff, that piqued her interest. “I was around ten or eleven, when I thought, I want to do that. I want to do this art that’s seen everywhere by everybody. New York [in the 1970s] was a bleak place, and [those posters] really did brighten the environment. And they were done by graphic designers.”
She went to Pratt on a scholarship and majored in graphic design, to follow in Glaser’s foot-steps. “[Milton Glaser] was my childhood hero. I wanted to get some experience before I graduated, so I looked up where his studio was and I literally knocked on the door.” Four days a week during her senior year at Pratt she interned for Glaser. “I consider that to be my de facto MFA program,” she says. “He was very open and accessible. He seemed to treat the interns and the people who worked for him and the clients all with respect. There were no prima donna tantrums in the studio, and that set a great example of someone who’s not only a wonderful professional but also a good human being.”

After graduation, Glaser recommended her to Henry Wolf, the famed advertising and editorial art director known for his work for Esquire and Harper’s Bazaar. “I worked with [Wolf] on his book, Visual Thinking,” she recalls. “Seeing how he put his images together and talking to him about his work was another great experience. Both [Glaser and Wolf were] wonderful visual communicators.”

Despite admiring her mentors, Weinstein had little patience for graphic design as a practice. “There were a lot of meetings and a lot of press runs. I just wanted to do the work. I wanted to create the images.” So she decided to beef up her illustration portfolio and hit the pavement.

Steven Heller, then art director for the New York Times Book Review and career-maker of many, gave Weinstein her first big break. She showed up at his early-morning portfolio reviews, along with countless other hopefuls, and waited for him to glance at her work and say, “Come back in a few months.” She says, “I actually went back to see him two or three times [over the course of a year] before he gave me my first job.” Although the details of that first job are hazy, the lesson of perseverance—which she passes on to her students—and the thrill of having her work published took hold. “I still remember the excitement of waiting down by my local newsstand on Saturday night for the truck to deliver the Sunday paper, so I could see it in print. I still feel that level of excitement when I have something big that’s coming out.”

Since 1991 she has been evolving her style as an illustrator. In the beginning she made monotypes, “and they were very dark and very serious,” she says. “It took me a while to feel more comfortable using my own personality. I had this sense that if I wanted to be taken seriously, my work had to be serious. Over time I’ve allowed myself to lighten up a bit and be more playful in my work.”

Weinstein is a believer “in the power of the single image,” which she attributes to her schooling with Wolf and Glaser. She also relishes deadlines and the constraints of working with clients. “I enjoy the collaborative process. I want to be happy, I want the art director to be happy, and the reader to be engaged. And I really enjoy the back and forth that that provides.”

When asked if she’s concerned about the obsolescence of typewriters, inkwells, clawfoot tubs and other visual metaphors common to her work, she replies, “That’s always an interesting conversation, and it’s one that I have with my students too, about what is a symbol and what is the shelf life of a symbol. That language is constantly changing. There are some symbols that are kind of time-less, and then there are some that are not.

“That’s what I love about illustration, the ability to play with that kind of stuff. It’s a great way to have that conversation with the public. Go through old magazines and see the illustrations that were done at the time, you really get a sense of what people were talking about, just because of the ephemeral nature of it. You can do something that refers to a reality show, the next week it’s on the recycling truck, and then we’re on to the next thing.”

At RISD, Weinstein says, “I run my classroom like an Amish village: they’re not allowed to bring in their laptops or do digital work for the semester.” But she’s no Luddite, and the computer is an essential part of her practice. “I use it every day. It’s a great tool, but a terrible place to learn. In school you have access to people who can really teach you how to draw and paint, so why not take advantage of that?”

The way she works: “I mark up a manuscript and distill it down to one sentence of what I want to say, and then start making scratches on paper and see where that takes me. I’m a big fan of wrestling with the white paper. Going out for a walk doesn’t help me come up with ideas.

“I’m much more inspired by what I see every day than things that are pure fantasy,” says Weinstein. “I think the quotidian is highly under-rated as a source of inspiration. Everyday situations, objects and just twist it into something new, it’s something I really like to play with.”

Despite many nostalgic references in her work, Weinstein is not the sentimental type and prefers to always be looking forward. When asked about future plans, she hedges. “Whatever I think my trajectory is going to be, it changes. It’s just being open to the opportunities that come up,” she says. “Two years ago I would not have predicted that I would now be the president of ICON8 or that I’d be teaching work-shops. It’s exciting that way. As much as I have a set routine—I keep very strict hours—I like the things that come in that disrupt that too.” ca