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Before Cardi B and after Lauryn Hill there E-v-e, the pit bull in a skirt from Philly who, in 1999, dropped the the third album by a female rap artist to top the Billboard 200.

At the time, Ruff Ryders’ First Lady was mixing masculine lyrics with feminine sex appeal via mini-dresses, peek-a-boo cleavage, and thigh-high boots and heels. But over time, the beauty’s image softened, her appeal widened, and we began to see an actress, entrepreneur, and woman who could spit hard lyrics in a striking ball gown with no problem.

Now as Eve turns 39, we take a look back at some of her earlier fashion choices and how she evolved over time to become an artist that didn’t just slay in the studio but on the red carpet as well.

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