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he was funny without being self-deprecating, which at the time seemed like the only permissible way for a woman (or in this case, a man wearing what were ostensibly women's clothes) to make appearance-related jokes

Mainly because the sparkling gown featured sheer peek-a-boo paneling which allowed all of the star's famous curves to be very visible

Fast forward to my early adulthood, and Im feeling like a traitor

It doesn't really matter what you wear underneath your jean jacket with this look (although we recommend a form-fitting pair of comfortable shorts and a sweatshirt), since the whole point is the contrast between the boots and the jacket