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.

1995

Depp proves opposite styles attract when hitting the scene in 1995 with his then-girlfriend, Kate Moss. In keeping with the era’s grunge movement, Depp looks roguish in a leather jacket, plaid button-down, and beanie. Meanwhile, Moss plays the role of supermodel girlfriend in a sleek black sheath.

1999

A more dapper Depp sports a black tuxedo jacket and charcoal-color shirt at the Los Angeles premiere of his 1999 movie, Sleepy Hollow. Vanessa Paradis, a French actress and Depp’s longtime girlfriend, steps in as his arm candy for the evening.

2004

For a London premiere of 2004’s Finding Neverland, Depp channels the debonair style of Old Hollywood greats with a ’40s-inspired suit, two-tone oxfords, a gray gabardine suit, a pocket square, and horn-rims. Surely Cary Grant would approve of his snappy style.

2005

At the premiere of The Libertine, Depp stays neutral with a boxy, camel-color suit, wide-lapel shirt, and brown oxfords. Staying true to his signature, retro-inspired style, Depp sports dark-rimmed glasses and a wallet chain.

2006

Looking like a modern-day Jack Sparrow, Depp pairs ripped jeans with a tailored blazer, simple tee, and fedora at the 2006 Pirates of the Caribbean: Dead Man's Chest press conference. Medallion charms draping over Depp’s jeans perfect his pirate-meets-hipster look.

2007

At 2007’s Venice Film Festival Lifetime Achievement Award celebrations for Tim Burton—one of Depp’s longtime friends and collaborators—the actor puts a playful twist on formal dress codes. Opting for a white dinner jacket, a bow tie, and loose-fitting trousers, Depp updates the old-school ensemble with silver rings and dark aviator shades.