Speaking candidly about her history of eyebrow problems, Olivia Wilde wishes she learned to put the tweezers down. “When I was five, after watching my dad shave, I took his razor and shaved my face—including my eyebrows. You look like an alien without eyebrows,” she said. “Then, in my mid-teens, I plucked them to create that sexy Kate Moss arch. I regret it because I damaged my follicles, and now it's hard for me to grow thick, bushy brows.”
Before making the “Rachel” cut a household look, Jennifer Aniston admits she took a few hair risks that weren’t so successful. "I can't even call it a risk, it was just bad judgement!" she told us in an interview. "We used to shave our heads just right above the ear, and now I'm like, why did I do that?"
Even Lauren Conrad, who has her signature look down pat, made some rookie mistakes early on. “The first time I was allowed to wear make-up was around the seventh grade,” she told InStyle’s Kahlana Barfield in an exclusive video. “I thought you were supposed to match your eyeshadow to your clothes, and I was just sort of playing around and figured it out along the way.”
Like most of us, Jamie Chung had her fair share of cringe-worthy moments during her high-school years. “I was in eighth grade and that was in the ‘90s so the coolest thing to do was wear brown lip liner but nothing else. And thin eyebrows," she says. "Not cool."
When we chatted with Debra Messing, the actress dished on the one throwback hairstyle she’ll never try again. “I certainly wouldn’t do the bi-level haircut that I had in high school, coupled with a perm. I just looked like a poodle.”
While we’re certain Julianne Moore can pull off just about any hairstyle, the famous redhead told us bangs probably aren’t her best look. "Oh my God, bangs! Always a mistake for me,” she says. “The minute I cut them I'm like, 'Why did I do this?' I have a cowlick at the front of my head, so they always split."
Although we think Vanessa Hudgens’ hair transformations have always been flattering, according to the star, she's no stranger to a slip-up. “When I was seven, I gave myself a bob and bangs. It was really sad. I looked like I had worms on my head," she confessed to InStyle back in 2009. "I went through a stage where I had burgundy hair, which was frightening, and I had light brown hair with light blonde highlights. It looked so bad! My friend said it looked like I'd dipped my hair in ashes."