In 1990, publicity doyenne Eleanor Lambert, founder of the International Best-Dressed List, celebrated its 50th anniversary by selecting from her scroll of 1,170 style leaders the “Fabulous Fifty, instant fashion symbols of the 20th century.”

As 2020 marked the 80th anniversary of the I.B.D.L.—a milestone for an institution whose imminent extinction has been prophesied for decades—we commemorate our long history by revisiting the annals of The International Best-Dressed List: The Official Story, and reviewing the year that passed, to spotlight 20 superlative honorees.

Millicent Rogers, by Louise Dahl-Wolfe; Babe Paley, by Horst; Marlene Dietrich; Grace Kelly, by Howell Conant.

Millicent Rogers (elected to the List in 1940): An audacious heiress with a penchant for folkloric and historical clothing mixed with (or designed by) Mainbocher, Schiaparelli, Valentina, and Charles James, Rogers appeared on Lambert’s first List, and the supremely inventive Standard Oil heiress collected, and wore, quantities of Native American jewelry, and became an advocate for the rights of indigenous people. Rogers’s idiosyncratic aesthetic has influenced designers from Geoffrey Beene to John Galliano.

Babe Paley (1941; entered the I.B.D.L. Hall of Fame in 1958): Designated by Lambert in 1974 as the “Super Dresser of Our Time,” society paragon Paley appeared, at age 26, on the second List the founder created, and on its first Hall of Fame. Unlike many Listees of her generation, the willowy second wife of CBS mogul William S. Paley patronized mostly New York–based designers, such as Charles James, instead of their Parisian counterparts. Even her most offhand gestures, such as tying a scarf around her handbag, could inspire legions of imitators. About the revered Paley, who once worked for Vogue, Truman Capote wrote, “[She] had only one flaw: she was perfect; otherwise, she was perfect.”

Marlene Dietrich (1951): Lambert praised the eternal movie goddess, humanitarian, and Dior enthusiast for her “indestructible glamour.” Notorious for her affinity for men’s wear—she claimed women’s trousers did not fit her—as well as for her risqué Jean Louis cabaret costumes, Dietrich said, “I dress for the image. Not for myself, not for the public, not for fashion, not for men.” Paramount wardrobe chief Edith Head considered Dietrich “a designer’s dream.”

Grace Kelly (1954; H.O.F., 1960): Kelly was only 25 and fresh from her Oscar win for The Country Girl when first elected to the I.B.D.L. Lambert lauded the former cover girl for her “calm immaculate clothes,” and columnist Eugenia Sheppard credited her with “the fad for short white gloves and the briefcase handbag”—now known as the Kelly bag. “I just buy clothes when they take my eye,” Kelly explained, accounting for her sleek, classic style, “and I wear them for years.”

Diana Vreeland, by Bert Morgan; Audrey Hepburn, by Bert Stern; Jacqueline de Ribes, by Mark Shaw; Gloria Guinness, by Cecil Beaton.

Diana Vreeland (1954; H.O.F., 1964): Lambert included Vreeland in her “Fabulous Fifty,” citing the formidable editor’s “profound impact on the world of fashion through her extraordinary personal flair and her professional inspiration.” With her outré makeup, scarlet-tipped fingers, attenuated wrists, and lean, sharp silhouette, Vreeland was a human hyperbole. “Exaggeration,” she noted in one of her oracular pronouncements, “is my only reality.”

Audrey Hepburn (1956; H.O.F., 1961): Hepburn first arrived on the List at age 27, not long after appearing on-screen in War and Peace. Struck by the starlet’s gamine grace, Lambert at the time called her “a fashion natural who can wear anything and make it look right.” Hepburn herself said that “clothes are positively a passion with me. I love them to the point where it is practically a vice.” Lambert counted the beloved Givenchy muse and exemplary UNICEF ambassador among her “Fabulous Fifty.”

Jacqueline de Ribes (1956; H.O.F., 1962): The perennial embodiment of Parisienne chic, the rarefied Vicomtesse de Ribes was compared by her friend Yves Saint Laurent to “an ivory unicorn,” and described by her disapproving father-in-law as a “cross between a Russian princess and a girl of the Folies-Bergère.” The subject of one of Richard Avedon’s most arresting portraits as well as of a Metropolitan Museum exhibition, the athletic, adventuresome aristocrat ghost-designed for Emilio Pucci in the 1950s and established her own acclaimed label in the 1980s.

Gloria Guinness (1959; H.O.F., 1964): Guinness was a particular favorite of Lambert’s, who felt the Mexican jet-setter was a “born beauty” with a “faultless figure.” An important client of Balenciaga’s, who considered her the most elegant woman he dressed, and partial to graphic ensembles of black and white, Guinness was responsible, Vogue observed, for “triggering, sometimes, a new direction in fashion.” A contributor to Harper’s Bazaar for eight years, Guinness was, in Lambert’s estimation, “the woman who has everything.”

Jacqueline Kennedy, by Steve Schapiro; Gloria Vanderbilt, by Douglas Kirkland; Diana Ross, by Steve Schapiro; Lena Horne, by Larry Ellis.

Jacqueline Kennedy (1960; H.O.F., 1965): As First Lady, Kennedy graciously set the tone for millions of American women. Remarkably, 60 years later, her look—low shoes, big sunglasses, neat ensembles, breezy hair—still remains a template for youthful, decorous dressing. Lambert found Kennedy’s style “very unaffected, very distilled,” noting her “casual ease” while off duty and “correct good taste in public life”—a formula that served her through changing circumstances. Valentino, who dressed Kennedy in the post-Camelot era, described his most visible client as “a mix of naturalness and sophistication.”

Gloria Vanderbilt (1962; H.O.F., 1970): Lambert’s voters elected Vanderbilt—an artist, actress, and designer—onto the List eight times before they deemed her to be Hall of Fame material. In the chaotic year of 1968, Vanderbilt was among those diverted by the I.B.D.L. committee into a splinter category, “Most Imaginative Women in Current Fashion.” Twenty-two years later, Lambert included the unorthodox patrician among her “Fabulous Fifty,” describing her in a press release as “America’s most appealing heiress/career-girl.”

Diana Ross (1978): In the 1960s, as a member of the Supremes, Ross’s slinky sophistication already stood out among her hitmaking Motown colleagues. But her super-diva style was not on full view until she broke out as a soloist. A devotee of Bob Mackie’s clingy, spangled, and be-plumed confections, Ross also had a hand in conceiving the flamboyant costumes for the 1975 film Mahogany, in which she played a designer.

Lena Horne (1981; H.O.F., 1983): Singer, dancer, actor, civil-rights activist, and one of Hollywood’s first Black movie stars, Horne was known for her showstopping wardrobe, whether concocted by Irene for MGM’s Cabin in the Sky (1943) or by Giorgio Sant’Angelo for Broadway’s Lena Horne: The Lady and Her Music (1981).Though during her storied career Horne was regularly typecast as a seductively sheathed nightclub performer, she celebrated her own individuality, sartorially and otherwise. “I’m me,” Horne declared, “and I’m like nobody else.”

Diana, Princess of Wales, by Georges De Keerle; Tina Chow, by Arthur Elgort; Iman, by Margaret Courtney-Clarke; Kate Moss, by Hannah Thomson.

Diana, Princess of Wales (1981; H.O.F., 1989): Disconcerted by her floppy bows, fussy ruffles, ballooning shoulder pads, quirky hats, and excessive “fervor for promoting British fashion designers,” the I.B.D.L. committee was initially convinced more of Princess Diana’s popularity than of her taste. By 1984, Lambert conceded that the Princess of Wales was “the world’s most influential woman of fashion today.” Not even the List’s farsighted founder, though, could have vaticinated the current Diana mania—a phenomenon that will be compounded when Netflix premieres Broadway’s Diana: A New Musical come May, and Pablo Larraín’s film Spencer opens in the fall.

Tina Chow (1982; H.O.F., 1985): Married to Michael Chow of the Mr. Chow’s restaurant empire, Tina entered the fashion world as a teen model, later earning renown as a prescient collector of vintage couture and as a muse to artists and designers. Tina was interested “in the spirit of the clothes and in being a medium of expression for the designer,” Issey Miyake recalled. In the late 80s, the androgynous beauty became an AIDS activist and a designer herself, making jewelry that drew upon her Japanese heritage.

Iman (1982; H.O.F., 1986): The Somali-born supermodel and entrepreneur helped break racial barriers in the fashion business and the beauty industry with her range of products for people of color. “The secret of my success is patience,” Iman said recently. Yves Saint Laurent, who featured Iman both on the runway and in an ad campaign, said, “My dream woman is Iman.” David Bowie apparently felt the same way when he married her, in 1992.

Kate Moss (2004; H.O.F., 2006): Though notoriously reluctant to give interviews, Moss has communicated effectively through her clothing. A multitude of turn-of-the-century trends—skinny jeans, slip dresses, parkas, Wellies, sloppy scarves, leopard-spot coats, outsize bags, bed-head hair—can all be traced, one way or another, to a paparazzo shot of Moss. In the early 90s, at the peak of “heroin chic,” some of Lambert’s judges dismissed Moss as “dirty.” But a decade later she rose effortlessly into the Hall of Fame.

Fran Lebowitz, by Annie Leibovitz; Lady Gaga, by Andrew Harnik; Rihanna, by David Fisher; Amanda Gorman, by Gabrielle Lurie.

Fran Lebowitz (2006; H.O.F., 2008): The recent Martin Scorsese–directed documentary series, Pretend It’s a City, has reminded us of Lebowitz’s dandyism. An aficionado of men’s jackets (some of them hand-me-downs from Geoffrey Beene), polished cowboy boots, and Hilditch & Key shirts, Lebowitz continues the trouser-wearing tradition established by 19th-century bluestockings (George Sand), artists (Rosa Bonheur), demimondaines (Napoleon III’s mistress Marguerite Bellanger), and by fellow I.B.D.L. honoree Marlene Dietrich. Dietrich and Lebowitz, in fact, were for many years the only two female patrons of Savile Row tailors Anderson & Sheppard. (More recently, Kate Moss became a third.) “I take very good care of my clothes,” says Lebowitz. She wears them for decades.

Lady Gaga (2010): Thrice elected to the List, Lady Gaga captivated us again with her musical and sartorial contributions to the inaugural ceremonies. From her controversial meat dress, with its echoes of paintings by Mark Ryden and Chaim Soutine, to her gilded Schiaparelli dove brooch, which hearkens back to Yves Saint Laurent and Georges Braque, Lady Gaga excels at turning herself into an ambulatory work of art.

Rihanna (2015): Millennials have an adage: “It’s ugly until Rihanna says it’s not.” Unintentionally, the singer, entrepreneur, and designer has launched fads for everything from micro-sunglasses and “thicc” body types to voluminous outerwear. With her rebel attitude, she instinctively converts any runway look into an eclectic statement entirely her own. “You will never be stylish if you don’t take risks,” the entertainer has explained. Rihanna also revolutionized the innerwear and cosmetics markets with her Savage x Fenty and Fenty Beauty brands, both predicated on consumer inclusivity.

Amanda Gorman (2020): The only first-timer on our 80th-anniversary List, the 22-year-old National Youth Poet Laureate fully embraces the metaphorical meaning of clothing. “It’s my way to lean into the history that came before me and all the people supporting me,” Gorman recently told Vogue. At President Biden’s inauguration, the Los Angeles native wore yellow Prada as a tribute to the First Lady, and a ring from Oprah Winfrey, in the form of a gold-vermeil birdcage, to salute fellow inaugural poet Maya Angelou.

Amy Fine Collins is an Editor at Large for AIR MAIL. She is the author of The International Best-Dressed List: The Official Story