Beauty Hair Hair Color Jennifer Aniston Spills the Details on Her Biggest Hair Risks Ever By Marianne Mychaskiw Marianne Mychaskiw Instagram Marianne Mychaskiw is a New York-based freelance writer and editor who covers everything from beauty and style, to wellness and entertainment. InStyle's editorial guidelines Published on May 9, 2014 @ 09:55AM Pin Share Tweet Email Photo: George Pimentel/WireImage Whether she's rocking long layers or a chin-length bob, Jennifer Aniston's hair never fails to induce envy (so much so that we're constantly trying on her covetable strands in our Hollywood Makeover Tool). The star is always open to changing up her style for a role, but long before she made the "Rachel" cut a household look, she was on-trend in the '80s when she experimented with hair risks like severe cuts and unconventional shades. "I can't even call it a risk, it was just bad judgement!" she tells InStyle.com. "We used to shave our heads just right above the ear, and now I'm like, why did I do that?" As the saying goes, history tends to repeat itself, and while the side-cut has regained popularity in recent months, Aniston admits that's one trend she wouldn't try again. "It all comes back," she adds. "What goes around comes around, and when it does, you're just like, 'Oh, I've done that.' Been there, done that!" The '80s were certainly an interesting time for hair, and during the decade of neon highlights and crimping irons, the star has also tried her hand at some DIY styling. While she leaves that job to her mane man Chris McMillan these days, Aniston, who is the celebrity face and co-owner of Living Proof haircare, admits that her color was often her own handiwork. "Sometimes my mom and I would have a day of beauty, and I'd give her a perm and highlights, then I'd color my hair Boysenberry," she adds. "The name of the color was Boysenberry, and it had this wonderful magenta hue to it in the sun. All of those years of making mistakes eventually lead me to be like, 'Oh, let's just leave your hair alone and let it be nice and pretty.'" And that it is! Click through our gallery to see Jennifer Aniston's transformation—from 1987, all the way to today.