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Whitley’s World: A brief history of Bad and Boujee Black Girl Style

Jasmine Guy’s Gilbert is the blueprint for ‘Insecure’s’ Molly, ‘Dear White People’s’ Coco, and ‘Living Single’s’ Regine

No other show explored the life of coeds from a historically black college as thoroughly as NBC’s A Different World. The show’s colorful characters gave us everything we didn’t know we needed, from a young black man who made solving for x extremely sexy to a free-spirited redhead who would certainly be on the frontlines of any and every Black Lives Matter protest today.

But if “bad and boujee” was trademarked last year by Migos, it originated on the fictional Hillman College campus and was created by the grande dame of the dorm known as Gilbert Hall: Whitley Marion Gilbert. The Louis Vuitton luggage-toting, siditty Southern belle, as portrayed by Jasmine Guy, had a legacy at the prestigious university that went back generations. At 5-foot-2, her frame was petite, but her style was colossal. The Whitley character not only reflected the most fashionable trends of the ’80s and ’90s, but she also influences contemporary style and serves as an inspiration for many young black women and black creatives today.

As one of the first examples of young, black affluence on television, Whitley paved the way for a long list of pivotal TV personalities. The Fresh Prince of Bel-Air’s Hilary Banks, Saved by the Bell’s Lisa Turtle, Living Single’s Regine Hunter, CluelessDionne Davenport, GirlfriendsToni Childs, Dear White People’s Colandrea “Coco” Conners and even Insecure’s Molly Carter all seem to draw inspiration from the Richmond, Virginia-born beauty queen who, now via streaming apps, continues to personify the style and essence of bad and boujee black girls everywhere.

“She’s not about trying to be white, or anything else — she’s being very black, and this is a very black situation.”

Her impact also went beyond the small screen. In 2015, when the show became available to stream on Netflix — its license agreement expired in 2017, and it is now available on Amazon Prime — Pinterest boards, Instagram handles and Halloween costumes (including one from yours truly) dedicated to mimicking Whitley’s style became a dime a dozen. But imitation certainly is the highest form of flattery, and nobody knows that better than Whitley Gilbert.


The Devil is in the Details

Thirty years ago this week, we got a first-class ticket to a historically black college in Virginia. A group of students evolved from inexperienced adolescents to dynamic adults. From 1987 to 1992 we came to know and love Dwayne Wayne’s nerdy swag, Whitley Gilbert’s siditty style, Freddie Brooks’ free-spirited eccentricity, Kimberly Reese’s steadfast levelheadedness and Ron Johnson’s zany antics. And although the show initially aimed to follow the coed life of Cosby kid Denise Huxtable (Lisa Bonet), it shifted its focus in the second season to the whole crew’s college experience and to Whitley and Dwayne’s love story.

A Different World touched on relevant social themes such as workplace sexual harassment and racial injustice, and it celebrated black heritage. It also featured iconic dayplayers such as Patti LaBelle, Diahann Carroll, Whoopi Goldberg, Jada Pinkett and even Tupac Shakur, ushering in a wave of classic black television shows. “It deepened,” said Jasmine Guy, “the tone of black sitcoms.” Guy is currently filming Mario Van Peebles’ new SyFy series Superstition, as well as season two of BET’s The Quad, which is set at a historically black college not named Hillman.

The cast of A Different World

NBCU Photo Bank

To authentically portray her, Guy says, she created a backstory for Whitley that helped bring her to life. She decided Whitley had attended a primarily white, private school — so for her, Hillman’s campus truly was a different world. “She thought she was black, and she is. But there are all different kinds of ways to be black,” Guy said. “And … the Hillman College experience gave her a new sense of who she was and the community she belonged to. I noticed in the writing how she grew. Over the arc of a season you could see that that character had a lot to learn.”

The show was mostly written by Susan Fales-Hill and Yvette Lee Bowser. Creating a character with as much style development as Whitley, and the whole A Different World crew, started with the script, says Ceci, who worked as costume designer on the show for five seasons (1989-92).

“You can’t unsee A Different World. You’ve seen it, it’s kind of engraved in your psyche.”

“The inspiration comes first from the writing,” she said. “[It] shaped who these characters are, absolutely and situationally. … Whitley is waking up in the morning, but what is she waking up to do? You should be able to turn your TV on mute … and kinda know what’s going on when you see the character. I’m supporting the dialogue and the intentions that the writer and director are trying to convey. I’m doing that visually, through the wardrobe.”

Ceci’s resume includes work on iconic shows such as Living Single and Sister, Sister (both of which are apparently being rebooted) and now she is drawing on that experience: She’s costume designer on Netflix’s Dear White People. Each of these shows features personalities communicated via style, a characteristic she says was used deeply on A Different World. “You’d never see Freddie Brooks wearing anything the Whitley character would wear,” she said. “Jaleesa wouldn’t wear anything Whitley would wear. Each of those characters are … being true to who they are.”

Whitley Gilbert is certainly in a world of her own. There aren’t many episodes in which the girl with the sass and twang isn’t draped in Chanel suits and/or silk scarves. Unlike so many college students who roll out of bed in sweats, Whitley spends her days in heels, fur coats and pearls. “She’s a society girl,” says Mel Grayson, a designer who worked on the show’s early seasons before Ceci took over as costume designer. “She was highfalutin.’ ”

Grayson, a Dallas native, drew his inspiration for Whitley from his own upbringing — and shows that featured affluent characters like the women of CBS’ Dallas (1978-91). “I kept it sexy and hip, taking elements of French couture … elements of Southern church ladies who sat in the front row,” he said. “I’d take a bit of that kind of styling and move it down a few levels. Cut off the shoulder pads, kill the big heels and the big ruffles but still make her regal, and still make her stand out as somebody that had class.”

Whitley’s wardrobe wasn’t cheap. Both Ceci and Grayson say they shopped at high-end stores such as the Dallas-based Neiman Marcus but also had to get creative to stretch what was a meager budget. They augmented new purchases with consignment shop pieces. Tailoring was important: It was hard to come by clothes that fit Guy’s petite frame. “There were clothes that you’d know [were] quality just by the way they fit the body,” Grayson said.

NBCU Photo Bank

“Everything had to be altered to fit her perfectly,” said Ceci. “Thought was given to each decision — is this fitting too close, or too tight? No, she’d wear silk, she wouldn’t wear cotton. She’d wear probably pink, not black. Black is too harsh. Every time you look at Whitley, she’s not out-of-place. Everything about her is supporting this one style aesthetic.”

Ceci would often swap basic original buttons for gold ones, or choose a classic pump over a slouched boot. The key was to capture an authentically upscale young black woman who consistently remained true to herself. Would Whitley wear an unbuttoned blazer? Would she ever have a pimple? If so, how many? That pimple question alone sparked a production meeting debate that lasted at least 30 minutes.

“Those are the details,” said Ceci, “that help subconsciously round out a character.”


Boujee — and black

The first season of A Different World received scathing reviews and is often ranked last on lists of fans’ favorite seasons. Season four — it begins with Whitley’s epic shade toward Dwayne’s new girlfriend, Kinu, and ends with Dwayne asking Whitley to marry him — is the best season, by far. And while season two was a goodbye to Bonet’s Denise Huxtable storyline and a largely white production staff, it was a hello for legendary director and producer Debbie Allen, who ensured the show was both authentic and unapologetic.

During Allen’s tenure, the show created endless opportunities for black Hollywood professionals and designers. The Howard alum even took the writing staff on “annual field trips” to the Clark Atlanta, Spelman and Morehouse campuses for inspiration. What emerged was a show that was very black. “When Debbie Allen came on the show in the second season, she made it more specific, and more clear who all these people were — including Whitley,” Guy said. “Because she did know people like that. She brought little things like, ‘How can y’all have a cafeteria with no hot sauce on the table?’ ”

Despite Whitley’s often insufferable entitlement and occasional disregard for peers outside of her tax bracket — in one episode she defends Kimberly’s scholarship from a company that hasn’t divested from South Africa and separates herself from the anti-apartheid struggle with a flippant “I don’t know those people” — Whitley maintains a shatterproof pride in her blackness.

“When Debbie Allen came on the show in the second season, she made it more specific, and more clear who all these people were — including Whitley.”

“Yes, she’s a socialite, she’s got her nose in the air, she’s got great hair — and it’s straight,” said Grayson. “She’s got a light complexion; she could pass the paper bag test. But she’s a girl that wants to be a black girl. She’s not about trying to be white, or anything else. She’s being very black, and this is a very black situation.”

“There’s a distinction,” Guy said. “And I guess that’s why they call it ‘bad and boujee,’ because there are bougie black people that are not trying to be white. I think that is a misnomer that Whitley was WHITEly. I was determined not to go into that direction because this kind of character does exist in the black community and has the same issues as her friends.”

For Ceci, communicating that black self-confidence through Whitley’s clothing meant altering the styles that luxury brands were creating, particularly as those styles weren’t often intended for black girls.

“A lot of times when you go to high-end stores, that classic look is a color palette that is better for blond hair and blue eyes,” said Ceci. “We can wear those colors, [and] we can be more bold. I tried to let Whitley … not try to emulate what an affluent white person would look like but what an affluent African-American young woman in college would look like. But that really didn’t exist [on television]. It was up to me to imagine what that looked like. The trick with her was trying to make her look affluent but still approachable.”

Throughout the show, Whitley comes to life draped in jeweled tones rather than monochromatic. She’ll wear cream pants with an emerald blouse, or pair a black pencil skirt with a golden peplum blazer. A delicately placed broach here. A chain-linked belt there. Classic, polished styles mixed with elements of youth. “The trick with her was color,” said Ceci. “If I couldn’t find something colorful, I would often dye things. If she wore all taupes and beiges it would be like, ‘OK, who are you?’ ”

Maintaining that authenticity was particularly important when it came to portraying Whitley’s wedding day. This was long before wildly popular black wedding sites and Instagram handles like Munaluchi Bride existed. Seeing a black woman in a bridal gown was rare. “Bride’s magazine would never, ever have anybody of color in their magazine,” said Bethann Hardison, a pioneering African-American runway model and advocate for runway diversity whose son, Kadeem, portrayed Dwayne Wayne. “If they thought to do it, it was maybe a bridesmaid — but that came a lot later. We never saw anyone in a bridal gown that was of color.”

NBCU Photo Bank

A Different World’s pivotal 1992 wedding episode gave viewers something they couldn’t get anywhere else. It not only featured iconic guests — including Joe Morton, Diahann Carroll and Orlando Jones, among others — but it also served up the proverbial peak of Dwayne and Whitley’s relationship. Whitley had been dating future senator Byron Douglas III (portrayed by Morton) and was at the altar when Dwayne interrupted, asking her to reconsider.

According to Guy, the whole scene was done in one take, and Dwayne’s epic “Baby, please!” followed by Carroll’s “Die, just die!” weren’t actually written into the script. The episode — in which Guy wore a delicately embroidered fit-and-flare gown with puffed, capped sleeves reminiscent of Princess Diana’s and a dramatic train with bow detail — put black and bridal in the same sentence long before anyone else would. And if anyone knows how to dress for a momentous occasion, it’s Whitley Gilbert. So the pressure was on.

“We were trying to go with something that was sophisticated but still Southern,” said Ceci. “Something that had some sweetness … not over the top but still a little sexy. It had to have a little bit of everything … this one dress, striking the balance of demure but still sophisticated — and not too mature or revealing.” Unlike other episodes where she had the chance to communicate who Whitley was in multiple outfits, Ceci had to sum up all the character’s elements in one ensemble. “Wedding dresses are a challenge,” she said. “I’ve got one shot.”

The pressure was also on for Guy, who knew seeing a black bride on television was particularly significant for young black women. “Little girls dream of those things, and they don’t necessarily know it’s possible for them,” she said. “All the little girls are looking at Whitley being bougie, getting knocked down, getting up and then realizing, ‘Look at what she had to learn before she got married.’ That’s what I’m hoping young people will see: Look what it took to get to this point, and look how it’s worth it.”

The gown, which was made in-house rather than purchased, not only matched Whitley’s boujee bridal needs but also echoed Bethann Hardison’s words to magazine editors: “Black people get married too.”


Whitley’s World

The impact of A Different World goes far beyond the small screen. Its storylines tackled topics such as HIV/AIDS, interracial dating and apartheid — and enrollment at historically black colleges and universities (HBCUs) drastically increased while the show was on in prime time. “The show was so contemporary at that moment,” said Bethann Hardison. “A Different World was the first show that ever tackled all the issues, from date rape to race relations. It’s a show that stands the test of time.”

Networks also started making room for more black TV shows. “We were a part of a wave,” said Guy. “I didn’t realize that we were the end of the wave. I thought the business had changed. And then it went back to very few black people. It wasn’t until cable, and the birth of all these other outlets, that the networks couldn’t afford to be so cocky about what they put on and don’t put on.”

As for Whitley, her style and boldness showed up in other shows. In the 1990s, the presence of affluent young black women became less rare with the creation of characters such as Lark Voorhies’ Lisa Turtle, Karyn Parsons’ Hilary Banks, or even Stacy Dash’s Dionne Davenport. There was also another strain of young female TV personalities who weren’t born with money but via hard work became accustomed to the finer things in life, such as Kim Fields’ Regine Hunter, Jill Marie Jones’ Toni Childs and Antoinette Robertson’s Coco Conners. That sensibility is also evident in Insecure’s Molly on HBO, as portrayed by Yvonne Orji, whose power suits and fashion sense are a contemporary remix on Whitley’s wardrobe. There’s also, of course, Olivia Pope of Scandal, who stakes a claim to bad and boujee herself.

“I think that is a misnomer that Whitley was WHITEly. I was determined not to go into that direction.”

The HBO show’s costume designer, Ayanna James, recently talked to Fashionista about the inspirations for Molly’s character. “As far as examples we’ve had on television, we have Kerry Washington on Scandal … who is a very popular character for her fashion, but that’s somebody that is a bit more confident than Molly. The inspiration behind Molly was, ‘What would a lawyer look like if she was really, really into fashion? If she was the person who might take a weekend off to go to New York Fashion Week?’ She lives in L.A., she makes money, she works in an office … run by the old boys’ club, so how do we balance that to make it fashionable and make it relevant?”

“I saw a lot of Whitley-esque influence in a lot of characters,” said Grayson. “In Living Single and Girlfriends. They were a bit more risqué, but they had that same sensibility.”

Ceci said she wasn’t as aware of the influence in real time. But looking back, she sees correlations. However, she said the clothes she chose for characters such as Regine and Coco signify more aspirational efforts than did Hillman’s own pride and joy. “The Regine character, she is like a Whitley character. She wasn’t born with money. She has … humble beginnings and is a little more sassy and expressive,” said Ceci. “Coco didn’t have the affluence that the Whitley character has. So while there might be some parallels in terms of trying to be pulled together … those two characters are never gonna be able to hit the mark in terms of the polish and the etiquette of the Whitley character.”

Guy said she was more aware of women who paved the way for her as Carroll did in Dynasty (1981-89). While she agrees that both Hilary Banks and Regine Hunter fall into the same category as Whitley, she said they each had unique characteristics. “We were all a part of that theme, we were just different in our bougieness,” she said.

Both Grayson and Ceci acknowledge that although Whitley can be antagonistic, even when you hate her, you still want to dress like her. “Now when kids look at Whitley,” said Ceci, “they feel like she’s like a baby baller. They’re like, ‘I wanna look like her when I grow up.’ ”

“It just made young girls realize that you don’t have to be that … dowdy girl and just wear … jeans and your old flannel shirt,” said Grayson. “You can pull yourself together and go to school … and look a little more elegant, and not care what other people have to say about that — because you wanna be dressed.”

And Ceci is proud and humble at the same time. “You can’t unsee A Different World,” she said. “You’ve seen it. It’s kind of engraved in your psyche. And perhaps subliminally that’s a reference point, or even consciously. … I don’t know if I defined what African-American female affluence was at that time, but … I’m just coming to embrace the impact the show had, and my part in it … I feel proud and privileged and honored to have … been a part of that.”

As a fan of fashionable jewels and a curator of fine art, Whitley knows that reprints are acceptable. But there’s nothing like the original. Although her character set a part of #blackgirlmagic in motion, no one has matched her level of polished sophistication, and perhaps no one ever will. Ms. Gilbert would have it no other way.

Danielle Cadet is a senior editor at The Undefeated. She's a fan of good food, good novels and good manners and has seen every episode of Frazier at least 12 times.