In a time of mass uncertainty, it can seem trite to look forward to award season. But after a year of quarantining at home, film and television have become a shared source of joy amid the perils of the pandemic. Sure, many of us have spent the last several months in nothing fancier than sweatpants, but how we dress has always been indicative of our collective psyche, and no other event quite represents the current state than a Hollywood red carpet. 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 Oscar looks that surprise and delight and that were truly indicative of the times.