15 Celebrities With Terrible Style Who Still Date Hot Women Image via Getty Images North America

Enrique Iglesias

Notable partners: Anna Kournikova, Samantha Torres

Enrique Iglesias' look, sadly, hasn't changed much in the last few years; decade even. In the 12 years he's dated Anna Kournikova, the Spanish singer has always worn trucker hats, rosary beads, leather bracelets, and his favorite thing to wear on tour, smedium v-neck tees. The only person who seems to care about the singer's Euro-trash/American-hick style is Cristiano Ronaldo, who Iglesias says "copies" his look.

Stay Connected with
Complex Style
blog comments powered by Disqus