Billy Porter's 2019 Oscar tuxedo gown tops the biggest red carpet fashion risks that paid off list — Christian Siriano's velvet skirt and classic lapels launched a decade of gender-fluid formalwear on every major carpet.

Rihanna's sixteen-foot Guo Pei train at the 2015 Met Gala ranks among the biggest red carpet fashion risks that paid off — handlers, stairs, and satin volume that became the defining image of 2010s benefit-carpet fashion.

Lupita Nyong'o's 2014 rainbow pleated cape ranks high on biggest red carpet fashion risks that paid off — technicolor Gucci layers read costume on paper and instant canon under global Oscar telephoto flash.

Cher's Bob Mackie naked-dress Oscar era anchors the biggest red carpet fashion risks that paid off sheer-dress canon — crystal mesh and strategic beading established the template decades before modern transparency tests.

Zendaya's light-up Tommy Hilfiger ballgown at the 2019 Met Gala matched Camp without Halloween shortcuts — a theme-night engineering triumph on the biggest red carpet fashion risks that paid off ledger.