Spreading the good (looking) word.

What do UNICEF and high fashion have in common? That might sound like the lead to a juvenile joke, but there’s a genuine answer: ambassadors. And no, it’s not meant to be a punch line. Just as the UN has tapped celebrities such as Angelina Jolie and Roger Federer to boost awareness for various goodwill campaigns, fashion houses enlist certain stylish personalities to preach the brand gospel. Enter the fashion ambassador.

As fashion jobs go, ambassadors rank among the more curious. They’re similar to, but not to be confused with, “muse,” “spokesperson,” “friend of” or “face of,” as ambassadors typically do not appear in advertisements, print or otherwise. There are countless variations on the ambassador theme and plenty of examples of the age-old designer/high-profile pal tradition: Hubert de Givenchy and Audrey Hepburn; Yves Saint Laurent and Betty Catroux and Catherine Deneuve, and Oleg Cassini and Jacqueline Kennedy Onassis. More currently, Marc Jacobs has Sofia Coppola, and Karl Lagerfeld has Amanda Harlech. Elsewhere, things hit closer to home: Kelly Klein was Calvin’s mannequin, Eliza Reed Bolen preens on behalf of stepfather Oscar de la Renta and Lauren Bush dons the wares of could-be-future-father-in-law Ralph Lauren. The list goes on. Each coupling has resulted in viral brand awareness—the touchstone of any ambassadorship—but many don’t quite fit the definition of the latest manifestation: unapologetic branding.

The ambassador term itself is at once incredibly vague and vaguely regal—a combination that explains its appeal to whichever clever publicist likely coined it—and has been part of the fashion lexicon for some time. Yet it means different things to different people. And considering the number of publicists and participants who expressed concern about the positive or negative tone of this story, it’s clear that the concept comes with significant mockery potential.

Celebrities, particularly label loyalists, make for obvious candidates. Renée Zellweger often treads the red carpet in Carolina Herrera, and earlier this year, Reese Witherspoon committed to wearing Nina Ricci throughout an entire awards season, a role she reprised at October’s Los Angeles premiere of Rendition. Such appearances are the stuff p.r. dreams are made of, while clearly providing the star with something more than a schmaltzy title. Yet the various terms of compensation are nearly impossible to confirm.

Outside of Hollywood, the fashion press bandies about the word “ambassador” aplenty in relation to many oft-photographed ladies-about-town who wear the same designer again and again. Overt label loyalty can suggest a somewhat formal relationship between a pretty girl and a fashion house, one that assumes that free clothes, at the very least, hang in the balance. Giorgio Armani has never been shy about the faction of social types he enlists as official ambassadors, including Eugenia Silva, Princess Mafalda von Hessen and Lady Helen Taylor, whose services were also reportedly retained by Bulgari at one point, all of whom have agreed to live an Armani-clad life in exchange for trips around the world and, one would assume, some sort of a stipend, wearable or otherwise.

Certainly many swans are not on the formal payroll. For example, New York social princesses Fabiola Beracasa, Olivia Chantecaille and Lisa Airan are often seen on the charity and fashion circuit wearing Fendi, Valentino and J.Mendel, respectively. They religiously attend house events and occasionally host them. But none of them carries the official ambassador torch for those houses, and each insists hers is nothing more than a case of good client/good friend of the house. Whether being a “good client” involves paying for their clothes is a matter apparently too tacky to discuss. Clothing transaction talk drew somewhat coded responses from these lovely ladies. “I’m not a big shopper,” says Chantecaille. “Stores are usually closed when I get out of work, but it’s on my wish list.” As for the grand getups she wore to Valentino’s 45th anniversary Roman extravaganza and New Yorkers for Children: “Some of them are loaned,” she says.

Meanwhile, Airan is more straightforward: “I am not paid to wear the clothes,” she says. “I wear Rodarte and J.Mendel because I love the clothes, which I buy.”

As for being considered a de facto fashion envoy, Airan chalks it up to early interest in the label. “If you’ve been wearing something early, before a house might have evolved, I think people think of you as an ambassador of the brand,” she says. “I’ve been wearing Gilles’ [Mendel’s] clothes since 1999 and I was wearing a lot of Rodarte early. But ‘ambassador’ is a funny term. It’s not like you’re working for these people.”

Yet some bearers of the title do in fact operate in a very official capacity. Tinsley Mortimer was anointed Dior Beauty ambassador in May. Some might deem it a dubious decision on Dior’s part. Mortimer’s plentiful press attention—she’s a gossip column fixture and is reportedly toying with the idea of reality TV—flattering and otherwise, seems to clash with the traditionally under-the-radar nature of ambassadors. “To be honest, I’d never heard of a beauty ambassador until Dior came to me with the idea,” she says. Mortimer has embraced the role that she defines as “someone who can offer a link to the world beyond the boardroom.” Considering that her first project—consulting on a new compact called the Jetsetter Palette, launching in November—called for Mortimer and her young social friends, including Beracasa, Barbara Wilhelm, Eleanor Ylvisaker, Shoshanna Lonstein Gruss and Minnie Mortimer, to board a Dior-chartered jet to the Hamptons, where a Dior-clad Mortimer introduced the others to the new palette over lunch at Patrick McMullen’s house, it certainly seems like a plum gig.

While smiling and socializing are a big part of the job, in some cases, the call of duty goes beyond. Cameron Silver, best known as the owner of Los Angeles vintage bastion Decades and co-owner of Decadestwo, recently was named brand ambassador for, oddly enough, both Pringle of Scotland and Boucheron. He insists that he has a similar, clearly defined role at both houses. “It’s much more than just throwing a dinner party,” he says before listing publicity, event planning, client relations and celebrity dressing among his duties. During Milan Fashion Week he hosted an event with Pringle designer Clare Waight Keller. “I was really there to help Clare connect with people in an organic way,” he says. “It’s not always easy for these people who are artists to work the room.”

Though Silver is up-front about being on the payroll at both houses, the other ambassadors interviewed for this story and the houses they represent were less forthcoming about money. In Mortimer’s case, Dior Beauty reps held that the terms of her contract hadn’t been completely worked out, but compensation consists of lots of free samples, and also Dior’s increased involvement in Mortimer’s charities of choice, particularly New Yorkers for Children. Meanwhile, Armani reps maintain that their ambassadors are not paid, though globe-trotting to Armani events and their wardrobes are gratis.

“I’m not a socialite,” says Silver, as if to justify his salary. “And this can be a very interesting thing to do if it’s not a vanity gig. Although it would be nice to just roll out of bed and have someone groom you.”

Also in the ambassador league is Inès de la Fressange, who has held court at Roger Vivier since 2004 when Diego Della Valle hired her to, as she says, “take the dust off an old house.” She chose the architects for and helped design Vivier’s Paris flagship, where she has an office as big as designer Bruno Frisoni’s. As far as her title goes, she’s practically indifferent. “In the beginning, everybody was asking me what my title was and I used to say I was the phone operator,” she says. “I do not like to have a precise word for my work and I don’t even have a business card. I could have one made, written: ‘Busy Inès, expert of nothing specially.’”

However busy she might be, de la Fressange doesn’t deny the perks. “I can have all the Vivier shoes and bags that I want!” she says. “I know, it’s a dream. But don’t hate me—it’s just part of my work.”