43. Ja Rule with the rare Burberry bucket hat in "Always on Time."
Burberry's been around since 1856, but before rappers were debuting fashion lines in Paris, no one in hip-hop really knew what it was. Gucci and Louis Vuitton were the monograms du jour for the longest, then Ja Rule put the masses onto the elusive tartan pattern from England. Yeah, Styles P had the Burberry bucket hat in "We Gon Make It" a few months earlier, but "Always On Time" was a No. 1 pop song that caused way more hip-hop heads to take notice of the brand. The famous plaid has been on full blast since.