It’s no secret: In celebration of InStyle’s 20th anniversary, we’ve become slightly obsessed with all things nostalgic. We’ve relived everything from the most talked about dresses to the most gorgeous red lips of the last two decades—we even broke down the ’90s fashion and beauty trends that made a comeback (jelly sandals anyone?)
For our latest trip down memory lane, however, we’re combing through the most jaw-dropping hairstyles of the last 20 years, starting with Winona Ryder’s trailblazing crop in 1994. Of course, Jennifer Aniston’s “The Rachel” (aka the most requested haircut of all time), and Demi Moore’s extreme makeover for G.I. Jane were equally throwback-worthy. Curious to see who else made the cut?
PHOTOS: See the Most Unforgettable Hairstyles of the Last 20 Years
For more, pick up the October issue of InStyle, available on newsstands and for digital download now.