Unquestionably fabulous, London Tipton — played by Brenda Song — always rolled up to the Tipton hotel in clothes that, no matter how expensive (very), always captured red carpet style of the time. Sequined tops, furry coats, and shiny headbands made London look like a true heiress, and Ivana the Pomeranian would totally agree.
Signature Style Tip: More is more, and you can never go wrong with the right hat. Some of London's personal favorites included a fuzzy white beret, a leopard-print chauffeur hat, and, of course, a sparkling tiara covered in diamonds.
Honorable Mention: Given that she often wore her high school uniform, Maddie Fitzpatrick — played by Ashley Tisdale — didn't have much variation in her wardrobe, but the outfits she did wear were the epitome of what it meant to dress cool in the 2000s, ruffled babydoll tops and cowboy boots included.