2019: Billy Porter

While many iconic dresses stood out due to their elegance and near-angelic design, one number that was worn by Billy Porter stood out for a completely different reason. The actor is already well known for his unique fashion choices. Perhaps one of his most popular attires was the one he wore to the Oscars back in 2019. When he went to the occasion, he caused a lot of eyebrows to rise with his velvet gown and fitted tuxedo jacket designed by Christian Soriano. He also wore six-inch boots designed by Rick Owens.

Like many of his ensembles before, this one certainly grabbed a lot of people’s attention. It quickly became regarded as one of the most memorable dresses of that year. In line with his style statement, he stated that he wore the dress because he wanted to challenge people’s ideas about masculinity to a certain degree.