Captain America: The First Avenger (2011)
Jim Mortia can be seen here wearing a headset beneath his cap, but it's fairly common knowledge that soldiers wouldn't have had access to that kind of technology during World War II. In fact, that kind of advanced technology would not be developed for another sixty years.
The Curious Case of Benjamin Button (2008)
The Curious Case of Benjamin Button was a blockbuster hit, but that didn't prevent a few minor errors from making their way to theaters. For instance, a scene meant to take place in 1945 depicts Brad Pitt in aviator sunglasses. Aviators were not invented until 1952, seven years after the scene was set.