French woman Suzanne Lenglen won Wimbledon six times between 1919 and 1925, but is also remembered for her then-flashy attire.
Helen Jacobs may have stuck with white sneakers, but in 1936 when she took to the court in a dark top and shorts, her look was considered masculine.
Alice Marble pictured during a Wimbledon match in 1939. In the late ’30s Marble began to favor polo shirts and shorts, both seen as more masculine choices for a female player.
Photographers were very much focused on Linda Siegel’s choice of attire during her 1979 match against Billie Jean King.
In 1982, Chris Evert sports her colorful, customized Converse court shoes, a lace dress with pops of red trim and matching wristband.
Detail shot of Chris Evert’s custom Converse.
Years after disco died, Anne White brought it back to life. In 1985, the Pony-sponsored American wore a formfitting bodysuit and headband in the tournament’s first round.
Detail shot of Anne White’s sneakers.
Anne White on the court in 1985.
Russian sex symbol Anna Kournikova was one of the first to put some serious skin in the game. In 2002 she wore a cutout, mid-section-baring dress.
Talk about a formal affair. In 2008, Maria Sharapova wore Nike’s tuxedo top. Was she mocking the tournament’s conservative tradition?
In 2010, Serena Williams dared to show some serious color under her regulation white ensemble — pairing her tight shorts with the Nike swoosh.
Decked out in Nike footwear, Venus Williams elevated the fashion stakes in 2011 with a backless playsuit from her own label, EleVen.
Detail shot of Williams’ Nike sneakers.