Madonna at the VH1 Fashion Awards in 1998 At the VH1 Fashion ... In this picture from an MTV performance, she looked casual in a striped top and a newsboy cap.

Madonna bundled up in style, wearing a black puffer coat, scarf, and oversized black sunglasses. Morris, who is 38 years younger than Madonna, kept it casual but coordinated with his girlfriend ...

Her work has also appeared in Newsweek, Parents Magazine, AOL, and Huffington Post. Though Madonna wore an uncharacteristically modest look while introducing Sam Smith and Kim Petras' performance ...