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18. 1961: Annette Funicello
Annette Funicello, best known as an iconic teen star and Disney legend, wowed fashion pundits at the 1961 Oscars with her flirty white mini dress. The tulle tutu skirt reached just below the knees and puffed out into a voluminous A-line silhouette, and was topped off with a demure lace bodice. It was the perfect look for the 18-year-old actress. 

Funicello was accepting the Academy Juvenile Award on behalf of fellow Disney actress Hayley Mills, who won for her portrayal in Pollyanna. This was the last award ceremony during which the Juvenile Award was presented.

In a 1961 issue of Teen Magazine, Funicello said that the “biggest night” of her life was accepting a special Oscar for Mills, who was at home in England at the time and unable to attend. Funicello was also excited to meet the presenter of the award, Shirley Temple (who is pictured in the blue caped dress.)

While it's unknown who designed the dress, in 1961 Funicello admitted she had to take her mother shopping so she could help the actor with impulse control. "I used to get a $10 weekly allowance. But I always was in debt. I would take my $10 and go shopping for a dress, and I would find one I liked for $40 and charge it. So I would be in debt for four weeks," she told The La Crosse Tribune. "Now I don't get any allowance. I take my mother with me when I shop." Relatable.