Donning a retro wavy updo and a sexy backless peacock blue gown, Lohan stars in a nautical-themed shoot captured by photographer Norman Jean Roy, who also had her posing on a boat in a racy champagne-hued halter-necked frock.
Inside, the 6126 designer defends her bad girl reputation to contributing editor Nancy Jo Sales.
"I've never abused prescription drugs," she insists in the interview, which was conducted prior to her jail stint.
"I never have -- never in my life. I have no desire to. That's not who I am.
"I've admitted to the things that I've done -- to, you know, dabbling in certain things and trying things 'cause I was young and curious and thought it was like, OK, 'cause other people were doing it and other people put it in front of me. And I see what happened in my life because of it."
The "Machete" star also assigns blame to her father, Michael Lohan, and friends who "cared for the wrong reasons."
"I think my biggest focus for myself is learning how to continue to get through the trauma that my father has caused in my life," she tells the magazine.
"I don't care what anyone says. I know that I'm a damn good actress.
"And I know that in my past I was young and irresponsible -- but that's what growing up is. You learn from your mistakes."
Let's hope so! To read more of the interview, visit VanityFair.com or pick up the October issue, available in New York and L.A. on Sept. 2 and nationally on Sept. 7.
In other celebrity jailbird news, check out Paris Hilton's surprisingly glam mug shot.