1987
When first landing in the Hollywood scene in 1987, Depp makes a good first impression in his James Dean–worthy leather motorcycle jacket and trilby hat cocked just so.
1990
The actor and his then-girlfriend, Winona Ryder, show up dressed to impress at the 1990 Cry-Baby premiere in Baltimore, Md. Depp’s head-turning yellow suit and skinny mod necktie play up his starring-role status in the fashionable film.