Oscars Flashback: What Heath Ledger, Reese Witherspoon, and Meryl Streep Wore On the Oscars 2006 Red Carpet
Trends may change from year to year, but some things—like black dresses, red lipstick, and Meryl Streep—are never out of place on the red carpet at the Oscars. Just as all of the glam above will almost certainly appear at the Oscars 2026 on Sunday, March 15, they were all present on the Oscars red carpet 20 years ago. The awards ceremony itself was full of surprises, from all four major acting winners—Reese Witherspoon, Philip Seymour Hoffman, Rachel Weisz, and George Clooney—being first-time nominees, Crash pulling off a best picture upset over awards season favorite Brokeback Mountain, and more. Not a surprise, however, was the outstanding style attendees displayed on the red carpet two decades ago. Nobody wears a classic black tux like Clooney, as he once again demonstrated in 2006, and Michelle Williams, attending on the arm of Brokeback Mountain costar and then-partner Heath Ledger, another master of menswear, could wear her canary yellow Vera Wang gown with artful tulle ruffles and an elegant train today, and nobody would bat an eye. Jennifer Aniston …
