London: Enrique Iglesias, who is normally such a well turned out and super styled man, was dressed rather shabbily as he took his boat out for a spin with long term girlfriend Anna Kournikova in Miami, Florida on Monday afternoon.
The pop star protected his head from the sunshine by wearing a white bandana and he teamed it with very torn jumper, the Daily Mail reported.
Although Enrique is usually a fan of sporting tight T-shirts he chose instead to wear a baggy grey Pony hoodie that had holes in the arms.
The 37-year-old Latino heartthrob, who was also wearing sunglasses, was thoroughly outdone by his glamorous girlfriend who looked as good as ever.
The 31-year-old former tennis player kept things simple in an all black ensemble that included a tight vest and a pair of velour jogging bottoms.
She had her long blonde locks up in a ponytail and out of her face as she wore cool shades and relaxed on the boat.
As the day went on and the temperature dropped, a flip flop wearing Anna pulled on her hoodie as her boyfriend continued to steer the ship.