German fashion giant Hugo Boss AG’s recent woes worsened on Wednesday when it plunged into a second quarter operating loss of 33.3 million euros compared to a profit of 700,000 euros in the year-ago period. The company, which has been forced to downgrade its profit outlook twice this year, said sales slipped two per cent to 175.5 million euros in the quarter, with sales of its Boss Woman range down 43 per cent to 6.4 million euros.