Earlier this summer, over a plate of Cecconi’s lobster spaghetti, the immensely talented red-haired artist (clients include Emma Stone, January Jones, and Amber Valletta) sent me into an absolute beauty tizzy with her wealth of red-lip trivia. “Coco Chanel was the first to really popularize red lipstick, and she wore it for herself—not for you, not for her man,” says Goodwin, who is also a celebrity makeup artist for the venerable house. “Chanel’s original 2.55 bag originally included a special compartment designed specifically to hold a bullet of red lipstick. This is how quintessential Coco thought red lipstick was to a woman.”

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 (“Did you know they crushed beetle wings for that shine?”), we solidified plans for a photo shoot that would celebrate the power of the ever-iconic red lip. While at times controversial (beloved for its beauty, scrutinized for its sensuality), 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.