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Long before her infamous Superbowl wardrobe malfunction, Janet Jackson was famous from a young age thanks to her brother's Motown band, The Jackson 5. At the tender age of 16, Janet broke out on her own with her eponymous debut album that topped at #63 on the Billboard Hot 100. Soon, Janet dropped the Jackson-little-sis act and became the sexy style icon she still is today. Thanks to her updated menswear uniform—blazers with shoulder pads, baseball caps—power dressing suddenly became sexy.