21 Outfits from the 1999 Grammys Red Carpet That Are So Retro It Hurts

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21 Outfits from the 1999 Grammys Red Carpet That Are So Retro It Hurts
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In a gold, shimmery minidress paired with strappy heels.

In recent decades, the Grammy Awards has seen quite a series of monumental red-carpet moments—from Jennifer Lopez’s viral deep-V Versace dress in 2000 to Lady Gaga’s enigmatic egg pod look at the 2011 Grammys. But even the most groundbreaking looks of today's vastly evolving fashion industry wouldn’t be without its early-aughts predecessors.

The 1999 Grammys, in particular, were a noteworthy occasion for dress, as every single Album of the Year nominee that year was a woman. Dubbed “Grammy Year of Women,” the ceremony recognized artists like Lauryn Hill, Celine Dion and Madonna for their outstanding musical achievements—and with that special group of honorees came some special looks.

Ahead, we reminisce on the simpler times of 1999 that have set today’s standard in Grammys red-carpet fashion. As we await this coming weekend’s dazzling ensembles, look back on Hollywood’s finest in their most retro form.

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