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Rick Rowell via Getty Images
Awards season is back, and the jewel in its crown—the Oscars—is upon us. Sure, most of us night spend our days in sweatpants and jeans, but we’re looking forward to the sartorial escapism that the Oscars red carpet will bring this year.
Since 1929, the Academy Awards has maintained firm footing in the zeitgeist not only by being a point of contention and conversation but also for history-making moments, including some of the best red carpet looks of all time. While some years are more memorable than others, we prefer to focus on the standout moments that made us smile. Sequins, satin, and sleeveless dresses may be timeless, but the best Oscars looks of all time aren’t always the safest bet—they’re daring, bold, and sometimes deemed “the worst” at first, but that’s what makes them iconic. Ahead, you’ll find the 49 Oscars looks that surprise and delight and that were truly indicative of the times.
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