Elizabeth Taylor | Golden Globes (1957)
Apart from the royal women, only Ms. Elizabeth Taylor herself could pull off wearing a tiara (esque) headband. Cinderella would be very proud of this look.
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Barbra Streisand | Oscars (1969)
Considering the fact that Streisand has “wowed” audiences from the beginning of her career, we wouldn’t expect anything but a perfectly modest look. Once a classic, always a classic.