What Makes a Portrait Good? Five Photo Editors Weigh In

Publications rely on stellar portrait photographs to illustrate some of their most important articles—namely, their profiles. It may be a cliché to say that a picture is worth a thousand words, but a portrait is often a reader’s entrée into a story and subject, and has the potential to make an article or magazine cover go viral. Annie Leibovitz’s 1980 portrait of John Lennon and Yoko Ono for the cover of Rolling Stone magazine—on the day of Lennon’s death—may be the most famous image in rock history. Then, of course, there’s the 2014 portrait of Kim Kardashian popping champagne on the cover of Paper, which proclaimed it would “break the internet.”

What the reader doesn’t see is the energy and extensive collaboration that often go into producing a single, print-ready image. Behind every published portrait, there’s a drama between an artist, a subject, and the publication team, each party with their own needs. Editors, creative directors, an editor-in-chief, and occasionally an advertiser may all weigh in on a shoot—as many as 8 to 10 people on any single portrait, estimated Lauren Brown, senior visual editor at Hearst Magazines.

The collaborative nature of the process distinguishes editorial photography from fine-art photography, in which one creative personality makes all the decisions about each frame. After an editorial shoot, photo editors are generally responsible for sorting through proof sheets with dozens of images, selecting the very best portrait photographs of the bunch. Ultimately, they’re often seeking novelty, technical excellence, and a certain ineffable quality.

Clinton Cargill, visuals director of Vanity Fair, called it emotional truth. When he selects a final picture for a story, he said, he looks for one where “the self-conscious mask” that subjects bring to a photo shoot “falls away, and we see what remains in its place.” London-based photographer Nadav Kander took one of his favorite portraits, of Patrick Stewart, for the New York Times Magazine, where Cargill previously worked. The black-and-white image features the actor draped in a cloak, his face half in shadow with his round mouth wide open, lips capping his teeth. Cargill noted how Kander achieved strangeness, scariness, and joy all at once.

Michelle Stark, senior photo editor at the Hollywood Reporter, offered a more technical assessment of what makes a portrait good. “Hands are important,” she said. Awkward hand placement can wreck a composition. Andie Diemer, visuals editor at GQ, discussed another significant technical challenge. “Photography is all about the lighting,” she emphasized. Diemer is a fan of Gabriela Herman, whom she describes as a master of light. Herman’s best-known project, “The Kids” (2017), features pictures of adults who were raised by gay parents. Their faces are bathed in natural light as they recline by a pool, lounge on patio furniture, or press against a window.

A portrait can be especially challenging when the photographer is assigned a subject who has already been captured extensively. “I’m looking for something surprising—something I haven’t seen before or didn’t know about the person being photographed,” said Emily Jan, art director at The Atlantic. As exemplars, she points to Heather Sten’s shoot of Amy Schumer running naked and pregnant through a park for the New York Times, and David Williams’s portrait of presidential candidate Andrew Yang making a layup for The Atlantic. Cargill echoes Jan’s concern: He and his team extensively research past imagery of a subject in order to prepare for and conceptualize an original shoot.

Context is important for famous figures, Brown noted. A portrait of a musician can be looser and more abstract—“an interpretation of that person’s style and skill,” she said. But when a politician is on set, she seeks clarity and technical perfection. “I want to see everything about that person’s face, their style of dress, their mannerisms, their posture,” Brown said. One of her favorite portrait photographers is Celeste Sloman, with whom she worked to capture a number of women who filled the roles left open by men caught up in #MeToo reckoning.