Jennifer Aniston has been easy to ignore as a style figurehead. She's no Sarah Jessica Parker, who routinely cobbles together looks that are interestingly pretty or stylish without intimidating her fans. Prior to dating Justin Theroux, Aniston's wardrobe seemed about as interesting as her movie roles. Her uniforms of boot-cut jeans, brown suede boots, and pashmina scarves for daytime, and tank or sheath dresses for the red carpet, were like the sartorial equivalent of Just Go With It — unremarkable, but packaged well enough for mass appeal.
Yet this was perfect for Jen's image as our American sweetheart: We loved her because she didn't need to try. She didn't need to wear clothes to make a point — especially when she had her love life to define her. Yet now that she's dating known hipster Justin Theroux, her love life seems to be defining her wardrobe in unexpected and hipster ways. She's gone from a boot-cut Lucky Brand poster girl to a slouchy, oxford-wearing, cool Manhattanite. She's not quite ready to join a McCarren Park kickball team, but she looks ready to sample the Tasti-D on Bedford. See her hipster evolution in the slideshow.