“Coco Chanel was the first to really popularize red lipstick, and she wore it for herself—not for you, not for her man,” says Rachel Goodwin, celebrity makeup artist.

Makeup artist Rachel Goodwin celebrates the high-impact red lip through the decades and updates the look in a collection of tutorials created exclusively for The Violet Files.

Somewhere between gushing over Winona Ryder’s imperfectly perfect matte red lips of the nineties and the mesmerizing shade of Queen Nefertiti’s crimson mouth, we solidified plans for a photo shoot that would celebrate the power of the ever-iconic red lip. The seemingly simple red lip has managed to make its mark throughout history. “It comes down to this: Red lipstick is bigger than the color. It has a voice,” Goodwin notes. “One that says, ‘You’re confident, you’re sexy’ in one little tube.”

Here, Goodwin enlists iconic supermodel Amber Valletta to show off her one-of-a-kind takes on signature red lips from six different decades.