Steven Klein shot half of the notoriously decadent duo at Gabbana’s home in Portofino, Italy, in 2007.
The director and his “ghoul-friend” at a Gunther Sachs party in Paris in 1972.
The Scottish actress (photographed here in 2011 by Juergen Teller; that’s her again on the cover below) is the contemporary embodiment of bold, eccentric style.
The Guinness heir and fervent supporter of traditional Irish arts is always recognizable in his dapper tweeds and ethereal beard and ponytail.
It’s rare that the same person can stylishly pull off camo, crop tops, gowns—and postmodern catsuits, as shown in this Craig McDean shoot from 2010.
For a 2003 Steven Klein shoot, the pop legend played a role that was equal parts yoga master and bondage aficionado.
Splish splash! The pop star goes tub-thumping with the Kaiser in 2011.
Aside from her early, crucial support of kindred spirit Alexander McQueen, the late fashion editor and icon was the muse of milliner Philip Treacy.
The New York–based artist (shown here in 2009) has sworn to wear only white forevermore.
The Pop-art standard-bearer and his Factory frontwoman in an Empire State of mind in 1964 (from our January 2001 issue).
A couple of years after donning Marjan Pejoski’s “swan dress” at the 2001 Oscars, the singer went comparatively demure for photographer Lise Sarfati.
Trecartin styled a number of his artist friends, including collaborator Lizzie Fitch (left) for a 2010 story photographed by Sebastian Kim.
The woman who brought punk to the fashion world has never been afraid to push buttons— or boundaries.
Helmut Newton once described the Vogue Japan editor at large and street-style heroine as a “fashion maniac.”
Mr. Garavani (standing, left) gathered a host of his friends to pose for our “The Chic at Play” story in 1978.
Though she usually favors a neo-fauve Lite-Brite palette, La Minaj was reimagined as a rococo beauty by artist Francesco Vezzoli for this 2011 shoot.
The two make up South Africa’s rap-rave group Die Antwoord.
Fashion’s bad boy, photographed in more jubilant times by Nick Knight in 2002.
Though she claims to loathe the word “eccentric” (she prefers “bohemian”), Guinness (shot here in 2011) has helped redefine its meaning in fashion—regardless of whether she’s even wearing clothes.
This 1968 photo of the surrealist legend and godfather of modern eccentric style was featured in a 2006 story.
Gaga has employed the Thierry Mugler designer as her fashion director since 2009.
The fashion icon (second from left) found herself amid models Dree Hemingway, Guinevere van Seenus, and Kirsten Owen (from left) in 2010.
The Dolce & Gabbana model lit up Paris’s Les Bains-Douches at a 1987 Christian Lacroix party.
Domenico Dolce (top), from Steven Klein’s 2007 shoot in Portofino.
In 1996—when this photo was taken—Harlech left John Galliano to become Karl Lagerfeld’s muse at Chanel.
The architect behind countless luxury stores credits a midlife crisis for inspiring his Mad Max–meets–the Village People look.
The late fashion editor and legend Piaggi (pictured here in 1972 with frequent collaborator Lopez, an illustrator) was described as a walking museum.