Courtesy InStyle Makeover
“I know this sounds terribly shallow, but I’ve been mapping out my outfits every day since I was little, even before high school,” she tells
. “I have a very busy mind — there’s a constant chitter-chatter up there — but what I’m wearing the next day? That’s definitely something that’s always been in my head before I go to sleep at night.”
And it’s no surprise she started her fashion obsession at an early age, given her stylish influences. “My aunt Julie introduced me to Barneys and designers at a very young age,” she says. “And my mom was a huge vintage freak. Even when I was 2 years old, I insisted on dressing myself. I still have this tattered blue and purple carnival dress that my aunt brought back from Spain for me that I wore every day when I was a kid!”
But despite her ability to rock couture with ease, Bilson still has one non-negotiable fashion priority. “I’m on an endless journey to be as comfortable as possible,” she says of how she decides what to wear. “I like to stay in my pajamas as long as I can.” Read more on Bilson in the fall issue of InStyle Makeover, on newsstands Friday.