Best: Taylor Swift’s Iconic Messy Curls at the 2006 CMA Awards
Taylor’s OG country era meant wild spiral curls and just a touch of controlled frizz. At the 2006 CMAs, she leaned into her natural texture with a deep side part, resulting in the perfect “I woke up like this” moment.
Worst: Taylor Swift’s Blunt Bangs & Chunky Highlights at the 2010 AMAs
Bangs can be a game-changer, but at the 2010 AMAs, Taylor’s long, pin-straight bangs were too heavy and poked her eyes. Add in chunky Y2K-style highlights, and the overall vibe skewed more “homemade” than haute couture.