In the 1910s, the Puerto Rico look of a loose, "undone" updo was inspired by Luisa Capetillo, while the more regal look in New York was inspired by Isabel Gonzalez.
In the '20s, women in Puerto Rico wore their hair out of their faces in an unfussy manner, while those in New York went for coiffed curls.
In the '30s in Puerto Rico, Julia de Burgos was the inspiration for the tightly curled hair, pencil-thin eyebrows, and dark lips. The "girl next door" look in New York was inspired by Diosa Costello in the musical Too Many Girls.
In the 1940s, the Puerto Rico look was inspired by women working in factories, while the New York look was a nod to singer Myrta Silva.
In the '50s, the curly hair and dark brows in Puerto Rico were inspired by activist Lolita Lebrón, while the more natural-looking beauty standards in New York were taken from actress Míriam Colón.
The straighter hair and bangs look in Puerto Rico in the '60s was inspired by actor and singer Lucha Villa. The New York look took after Rita Moreno in West Side Story.
In New York in the '70s, the headscarf and braid were a nod to poet and graphic artist Sandra Maria Esteves.
In the '80s, beauty trends in both Puerto Rico and New York were characterized by colorful makeup and big, curled hair.
The straight, brushed hair of the '90s in Puerto Rico is a nod to the Miss Universe Pageant, while the curly-haired New York look is inspired by actor Rosie Perez.
Puerto Rico won two Miss Universe titles in the 2000s, which is where this look's inspiration was taken from. In New York, the red-carpet-esque look was inspired by Rosario Dawson.
As for the 2010s, the smooth hair and smoky eye makeup in Puerto Rico was inspired by 2016 Miss Puerto Rico Brenda Jiménez. The New York look of a Yankees cap, fur hood, and lip gloss was inspired by Jennifer Lopez's music video look for "Same Girl."