At the downtown L.A. apparel maker’s annual meeting Thursday, shareholders voted against a proposal that would have boosted the total number of shares the company can sell, effectively limiting the amount of cash the company can raise by selling additional equity.

The board had wanted shareholder approval to increase the number of authorized to 460 million, double the current authorized-share count of 230 million. The hundreds of millions of additional shares could have been sold to investors to raise needed capital for the firm, which has not been profitable since 2009 and is deeply in debt. But following Thursday’s vote, the clothing company’s options for raising cash have narrowed.

Veteran L.A. investment banker Lloyd Greif said the shareholder vote has a “huge” impact on the company and has effectively tied the board’s hands.

“In my view, this is the shareholders telling the board to sell the company,” Greif said. “I think the shareholders have had it with Band-Aid solutions. They’ve run out of patience with all of the disappointments with the company over the last few years.”

Greif said he sees the company going private in the future and possibly being acquired by a seasoned private equity firm.

American Apparel representatives did not return requests for comment.

Shares of American Apparel closed at 34 cents Friday, up about 2 percent on the day.