49. Rihanna

This might be hard to believe for some of our younger readers, but there was a time during the 1990s when every fashion-conscious guy had curtains as their hairstyle. That parted, floppy fringe was the look that every guy tried to grow out, and every girl went crazy for. If you could pull it off, then you too could have the pick of the girls as your prom date. Even if that girl was future pop star, Rihanna!

She may have made her name as a 'rude girl,' but Ri-Ri looks anything but rude here. In fact, she looks quite shy and demure. She certainly knew how to dress for the occasion even back then though - she's managed to pick a dress that blends in with the decor of the venue. We wonder if she was using it as camouflage to hide from her date on the dance floor?

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