Jennifer Lopez’s Best Red Carpet Looks From Every Year (2 of 14)

1998: Grammy Awards

To her first Grammy Awards, JLo wore a flashy blue knitted halter dress with a cute matching cardigan. By today’s standards, this look was pretty tame, but ever so ’90s.

1999: Academy Awards

She wore a strapless black Badgley Mischka ball gown that perfectly embodied the Hollywood princess aesthetic. That enormous skirt was a classic sign of “I’m going to dominate this red carpet event.”