Since we have been on the subject of clothes...how can we forget The Dress? Oh, how I love this dress. In 1980, from her Breakfast Club days, we saw the photo on the left in her first Rolling Stone cover - Madonna Goes All Way. In the middle picture, she resurrected The Dress gloriously in 1986. In the final shot, leaving Speed the Plow. Some trivia: Jennifer Grey wore The Dress with the black belt and all in 1988 when they were hanging out. The Dress made its final appearance in her 1989 calendar seen below - looking very much like the first shot - Bella Madonna!