Era of Prominence: Mid 2000s-present 

Fact: Jay-Z's bank account allows him to spend thousands of dollars on clothes. And while he certainly does that at times, he still appreciates a good graphic T-shirt or hoodie from some of the best streetwear brands, particularly Pharrell's Billionaire Boys Club. Hov's been rocking and name-dropping BBC since the early 2000s and, to this day, gives it his co-sign—as a partner.