Though a failure as a player, "the special one" has excelled in managerial roles in each of the most important leagues in Europe. Though the guys on the pitch get more nods for their sartorial glories (and mistakes), one can't deny Mourinho's exquisite taste. Perfectly tailored suits match the precision of his teams. If you are to follow one man in football for fashion advice, you'd be good with Mourinho as guide.  

Years Active (player): 1980-1987 (four clubs).

Years Active (manager): 2000 (Benefica), 2001-2002 (Uniao de Leiria), 2002-2004 (Porto), 2007-2010 (Chelsea), 2008-2010 (Inter Milan), 2010-present (Real Madrid).