The Best Dressed Artists of the 20th Century

The Best Dressed Artists of the 20th Century

In a century which would change art forever, we look at the best dressed artists.


Elsa Hildegard Baroness von Freytag-Loringhoven (1874-1927)

Known as Baroness Elsa, the German avant-garde artist was part of the New York Dada movement. Significant in Marcel Duchamp’s Fountain, the Baroness was an extravagant powerful woman who was once arrested for walking down Pittsburgh smoking a cigarette in a man’s suit. In the only few photos available of her, she is wearing whacky overseas inspired garments that include an array of wonderful custom-made hats. In the fall 2002 ‘Fashion Issue’ of the New York Times, the late actress Brittany Murphy paid tribute to the artist by dressing up as her for a Baroness Elsa inspired photo shoot. 

Pablo Picasso (1881-1973)

Arguably one of the most influential artists of all time, Picasso’s simply styled fashion sense was a cordial balance to his ever-changing artistic methods. Focusing on his later years, Picasso’s old-fashioned high waisted wide length trousers were a statement piece of his, that he often wore within his studio. Accompanied by these were cropped t-shirts or polos that would cover his barrelled chest creating a broad, but stylish silhouette.

Salvador Dali (1904-1989)

What outfit could not go with Dali’s moustache? The man had his own book named after it. The eccentric Surrealist artist dressed smartly throughout his career, having an acquired taste for three-piece or double-breasted suits. He also once wore a suit jacket that he customised with real champagne flutes for the print. The flared trousers in the youthful picture below make Dali impossible to leave out on this list, oh and of course The Persistence of Memory. 

David Hockney (1937-present)

The only Englishmen on the list, Bradford born artist David Hockney matched his modern colour palettes to his clothes. Not changing his style throughout his lifetime, Hockney wore brightly coloured spotted or stripped pieces that would illuminate his outfit. Accompanied by his signature round glasses and love of ties, Hockney looked like an accumulation of pop artist and mad professor. 

Keith Haring 1958-1990

LOOK AT KEITH HARING WEARING THE AIR JORDAN 1. A graffiti and pop artist from New York, Haring first received public attention when he would draw with white chalk on blacked out advertisement boards on the subway. Bomber, leather and varsity jackets with colourful patched or printed trousers were commonplace for Haring, and his devotion to Nike trainers rounded off his streetwear inspired outfits. His fashion sense was courageous and would have seamlessly fitted into the modern street style of today.

Jean-Michel Basquiat (1960-1988)

African-American Jean-Michel Basquiat was the star of the art scene in 1980s New York. Starting out as a graffiti artist, Basquiat exuded confidence through his abstracted artworks, fearless personality, effortless style and wild haircuts. He mostly wore oversized fitting clothes such as flannel shirts, wool jumpers, and long lengthened coats. His swagger and style were recognised by Rei Kawakubo in 1987 as he walked for the Comme des Garcons Homme Spring/Summer collection.



Cover image- Jean-Michel Basquiat. ®Edo Bertoglio, courtesy of Maripol Artwork. ©The Estate of Jean-Michel Basquiat. Licensed by Artestar, New York.