Approximate lifespan: 1976-1990

Like the other famous Will Smith, designer Willi Smith also hailed from Philadelphia. That's  about where the similarities end. Founded in 1976, WilliWear and its designer quickly became one of the most successful fashion brands by a black designer, selling about $25 million worth of clothing in the mid-80s. His collections were known for being as bold as they were affordable (uncharacteristic of a high fashion designer at the time), and he was a pioneer in experimenting with pattern and color in menswear. In 1985, he earned a Cutty Sark award for his men's designs, and shortly before his untimely death in 1987, his work was cemented in pop culture history when he designed Mary Jane Watson's wedding dress for the Spider-Man comic books.