5. Rihanna
The Valentine’s Disaster. Bad Girl RiRi is usually a fashion icon, but even icons make mistakes. She arrived in a massive, voluminous pink couture gown that the internet immediately roasted.
Memes compared her look to a giant loofah, a cupcake, or an “unflattering Valentine’s Day bouquet.” It was a bold risk that unfortunately landed her on every “Worst Dressed” list of the decade.
6. Jennifer Lopez
The Queen of Glow. In 2015, J.Lo ditched her usual tight silhouettes for a fairy-tale moment in Elie Saab. And it was perfection. The plunging neckline kept it sexy (it is J.Lo, after all), but the massive skirt covered in thousands of beads screamed Hollywood Royalty. The champagne color perfectly complemented her skin tone. This is what an Oscar winner is supposed to look like.
7. Andra Day
Drama on the Floor.
Singer Andra Day didn’t just walk the carpet; she owned it—literally lying down on it at one point! Her 2018 dress featured a busy floral print that reminded many of grandmother’s curtains or palace upholstery.
Paired with a massive ponytail full of real flowers, the look was theatrical, unique, and undeniably loud. You might hate the print, but you can’t ignore the confidence.
8. Miley Cyrus
Rock & Roll Elegance. Miley has come a long way from her Disney days. For this event, she struck the perfect balance between edgy and classy. Wearing a black sequined Yves Saint Laurent gown with a plunging neckline, she looked fierce. The look was topped off with heavy Bvlgari snake jewelry wrapping around her neck. It was dark, expensive, and incredibly stylish.
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