rocawear*It was pretty darn obvious that Rocawear was on its way out when even Jay Z (shown above) stopped wearing the clothes. But some people just have to learn the hard way. Take the Iconix Group for example.

The company purchased Rocawear for $204 million in 2007. Shortly thereafter, business bombed. The urban line once racked up $700 million in annual sales. But like the Dow on Wall Street, Rocawear’s appeal eventually diminished among young consumers, and so did revenue sales.

The company has hit a financial bottom, a new lawsuit claims. A New York City wholesaler is battling Jay-Z’s clothing label over a six-figure debt.

iSource NYC filed suit against Rocawear to recover $450,000 leftover from a $1 million order. Court papers state that iSource manufactured “specially ordered goods [with] the ‘Rocawear’ brand name imprinted on [them],” and shipped them from Pakistan to the Big Apple in April 2012.

The order was fulfilled, but as of last summer the payments dried up. iSource is suing for the outstanding balance plus 9 percent interest.

Rocawear’s struggles have been ongoing as of late — from being exposed for using dog fur to a $500 million sales dip and slicing its staff in half.

Even with contracting Ciara as a spokesmodel, a partnership with Pharrell Williams‘ Billionaire Boys Club and a deal to sell clothing out of Brooklyn’s Barclays Center, the company still hasn’t been able to climb out of debt.