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.
In an Atelier Versace gown, Gomez wore more fabric to the Spring Breakers premiere at the 2012 Venice Film Festival than she probably wore in the entire film.
Again in strapless Atelier Versace and newly single, Gomez switched into this metallic dress to party after the 2013 Golden Globes.
Her Atelier Versace gowns got more ambitious over the years: This navy on 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.
Starting 2016 off in red leather Louis Vuitton, Gomez hung out with Nicolas Ghesquière at a UNICEF benefit in L.A.