Winona, Cate, Timmy, Gwyneth: The 38 Most Eye-Popping Oscars Red Carpet Debuts

The prospect of attending your first Oscars ceremony is daunting, to say the least. What on earth will you wear? Who should you bring? And, if you’re lucky enough to be nominated, what should you say if you—whisper it—happen to be called up to the stage?
Ahead of the 2026 Academy Awards on March 15, we revisit some of the most jaw-dropping Oscar red-carpet debuts in history, featuring a bevy of Hollywood A-listers who navigated their first appearances like a pro—and went on to win or be nominated for their fair share of statuettes. This year’s crop of first-time nominees, for one, are just as buzzy as the last few generations of stars—Wunmi Mosaku! Rose Byrne! Jacob Elordi! Michael B. Jordan! Newbie attendees also include the likes of One Battle After Another’s Chase Infiniti and Sinners’s Miles Caton.
From a Crouching Tiger, Hidden Dragon-era Michelle Yeoh to a 17-year-old Winona Ryder attending with her then-boyfriend Christian Slater, and Timothée Chalamet before he really went in on the awards campaign—see our shortlist of the best, below.





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