PRINCE 27TH GRAMMY AWARDS, 1985 In full rock-god form, Prince managed to ooze sex appeal as he performed in a gender-blurring ensemble of a lace two-piece outfit with heeled boots. As always with Prince, the look was amped up and showed off why he was such a sartorial pioneer— taking an androgynous and experimental sense of personal style to the next level.
THE JUDDS 28TH GRAMMY AWARDS, 1986 Naomi and Wynonna Judd—country music’s most famous mother-daughter duo—show off their affinity for high hair, shiny fabrics, leopard prints, and padded shoulders in complementary looks fitting of another mid-’80s cultural phenomenon: the prime-time soap opera “Dynasty.” JIM SMEAL/WIREIMAGE.COM
RUN DMC 30TH GRAMMY AWARDS, 1988 Consider Run DMC the godfathers of streetwear. Run, Jam Master Jay, and DMC greatly influenced the future of fashion as we know it. Their typical style trifecta included Adidas tracksuits and sneakers, chunky gold rope chains, and fedoras. For the GRAMMYs, the trio took it up a notch, opting for matching leather Adidas jackets. Their allegiance to Adidas resulted in the firstever endorsement deal between a music act and an athletic company. RON GALELLA LTD./WIREIMAGE.COM
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