Oprah Winfrey’s Fashion Evolution in ‘Lee Daniels’ The Butler’

In ‘The Butler,’ Winfrey is Gloria Gaines, wife of a White House butler. Isabel Wilkinson on her evolution.

Anne Marie Fox/The Weinstein Company

Lee Daniels’ The Butler tells the story of Eugene Allen, who worked as a butler in the White House for 34 years. Allen was on the front lines of some of the most important events in American history, from Jim Crow to the assassination of John F. Kennedy, from Birmingham to Watergate.

In the film, Allen is Cecil Gaines (Forest Whitaker), a dignified, honest man who serves a changing cast of presidents (Robin Williams, Liev Schrieber, and more), while his wife, Gloria (Oprah Winfrey), presides over the home. She is the first lady of the Gaines household—and her style tells the story of what it meant to be a person of color living a stone’s throw from the White House in the last half of the 20th century.

Oprah’s Gloria, ever the spectator, watches history unfold from her front porch. She’s just out of the action as her husband goes to work in the Kennedy household, and her son Louis is sent off to college and becomes a Freedom Rider, a follower of Martin Luther King Jr., and then a Black Panther. Fittingly, her fashion choices evolve to reflect the styles of the times, and what Gloria wears at home reflects, in some small way, what’s happening in the country.

She first appears onscreen in the late 1950s, flitting around the breakfast table in a negligee. She’s sexy—a fiery young stay-at-home mother, the kind of person who might have a drink before noon. And soon she becomes that woman, a stately housewife with a wild side who smokes, develops (and then overcomes) an alcohol addiction, and even sleeps with her neighbor, Howard (Terrence Howard).

At the dawn of the ’60s, she’s refined, hosting a party for her husband when he gets the job at the White House in a figure-hugging three-quarter-length orange dress with a bow that’s reminiscent of Joan Holloway on Mad Men. When Kennedy moves into the White House, Gloria begins to emulate Jackie O. and frequently badgers Cecil to tell her how many pairs of shoes the first lady owns. Jackie (Minka Kelly) appears in a few scenes in typical pillbox hats and Oleg Cassini-inspired designs, which quickly trickle down to Gloria and her sewing machine.

Oprah beautifully portrays Gloria, a sassy, well-to-do woman who as the “first lady” of a White House butler would have been a pillar of her community. During one pivotal scene in which she and Cecil send Louis off to college, Gloria goes to the bus station with her hair covered by a scarf. According to the film’s costume designer, Ruth Carter, director Lee Daniels was adamant that Gloria’s hair be in curlers during the scene. “Oprah kept saying, ‘She wouldn’t do that! She wouldn’t go out of her house and let her neighbors see her looking like that—because she was married to a man that worked as a butler at the White House!’” Carter recalls. Eventually, the scarf was selected as a compromise.

The contrast between Gloria’s style and the world around her is brought into high relief when Louis, a newly minted Black Panther, brings home his girlfriend, Yaya, for dinner in 1969. Yaya wears her hair in a giant Afro, along with hoop earrings, a low-cut black tank top with no bra, and, of course, loads of armpit hair. Gloria, meanwhile, is the picture of a progressive housewife embracing trends, wearing a brown and cream Pucci-inspired jumpsuit with palazzo pants. (The sartorial culture clash is a foreshadowing: mama slaps Louis and kicks him out of the house.)

In a film that moves as quickly as The Butler, Gloria’s outfits serve as benchmarks to establish a decade. That’s never more clear than when Gloria watches Soul Train in a black and white jumpsuit she’s sewn herself, identical to one she’s made for Cecil, who actually puts it on. In that scene, Gloria is now herself wearing a kind of Afro, evidence of the trickle-down effect of hairstyles. As Carter puts it, “The Afro was a symbol of protest in the ’60s. It was a revolution, black is beautiful. But as time went on, as we see Oprah in a jumpsuit, she’s in an Afro with big hoop earrings. That to me said, ‘This is what became of it.’ It started out as a protest—and it ended up as a fad.”

By the 1980s, the Gaineses are invited as guests, not the help, to the Reagans’ state dinner, where the president (Alan Rickman) and Nancy (Jane Fonda) greet them with the sort of forced friendliness that leaves Cecil with a pit in his stomach. Now in old-age makeup, Oprah’s Gloria comes dolled-up, in a Dynasty-inspired silver and black gown (a real vintage piece that was re-beaded for the film), fancy but modest, eager to fit in with the crowd.

But perhaps the funniest outfits of the films are the ’80s tracksuits Cecil and Gloria wear to visit former slave quarters, which are matching and equally hideous. Carter remembers that Oprah directed her to find the “ugliest” tracksuit she could find. As Lee Daniels put it, “I think [those tracksuits] were indicative of where we were going in the film, that though we’re talking about very serious subject matter in the film, we still aren’t taking ourselves seriously when they get out of the car wearing the ’80s tracksuits. You don’t know whether to laugh or to take it very seriously.”

The film ends—a spoiler, though I’m not giving much away—with the Gaineses at an Obama party in 2008, all in matching T-shirts from the campaign. It’s, as Carter describes it, an “a-ha moment” that shows the audience how far the movie has come over time—and paints Cecil and Gloria as community elders ready to elect the first African-American man to the White House.