Just 16 at the time, Gomez was only one year into Wizards of Waverly Place when she wore this toga-like Marchesa gown to the American Latino Media Awards in 2008.
A year later, Gomez tried out red lipstick and a shorter hemline at the 6th Annual Hollywood Style Awards.
Doing her duty as a Disney star, Gomez showed up at the Kids' Choice Awards in a cheery yellow dress and a casual braid.
This Marchesa ensemble was hardly the first – or last – ice skater look for Gomez. It was also just the first of nine outfits that night, which had her hosting the 2011 MTV Europe Music Awards.
Gomez wore a voluminous Atelier Versace gown to the Spring Breakers premiere at the 2012 Venice Film Festival. It may have been more fabric than she wore in the entire film.
A newly single Gomez wore this metallic, strapless Atelier Versace dress to a party after the 2013 Golden Globes.
Her Atelier Versace gowns got more ambitious over the years: This navy number at the 2013 MTV Video Music Awards relied heavily on teeny silver clasps.
Gomez switched it up with tied-back hair and Dior at a screening of her 2014 film, Rudderless.
Gomez showed up to the "China: Through The Looking Glass" Met Gala in a tasseled Vera Wang gown and a headpiece made of orchids.