Jo Heywood, who runs a £30,000-a-year girls' boarding school, Heathfield, in Ascot, Berkshire, said the twerking popstar and the reality TV businesswoman sent out misleading messages as role models.
Miley Cyrus has gone from being a squeaky-clean teen in Hannah Montana to a scantily-clad gyrating sex bomb. Medically-trained Leah Totton showed determination and nous to win The Apprentice – but now wants to open cosmetic surgery clinics.
Now Mrs Heywood hopes the success of athletes such as Jessica Ennis and Victoria Pendleton at the London Olympics will give girls a new generation of women to admire.
She said it seemed that 'finally women were being recognised for their achievements rather than their looks, which reality show they were on or which celebrity they were dating'.
She said: "As head of a girls' school, I have long been yearning for more appropriate female role models for today's young women.
"We knew what these sportswomen stood for: hard work, sacrifice and achievement. They were clear-cut role models for young women.
"A year on, I am not so sure that anything has really changed. I am more than a little concerned that some of the so-called role models young girls may look up to are giving them confusing, mixed messages.
"Fast forward to another example of how young women are being manipulated and confused by potential role models.
"Many young girls have grown up as fans of Hannah Montana. Hannah, played by petite and pretty Miley Cyrus, was the archetypal all-American teenager: a girl to look up to.
"A few years later and we find Cyrus giving a headline-grabbing and controversial performance at the MTV Video Music Awards. Worryingly, Miley has apparently said she does not know what all the fuss is about.
"However, there is plenty to be concerned about, especially when these once clean-cut role models steer another course so publicly."
Writing on the Independent School Parent website, she also pinpointed Leah Totton, the 24-year-old doctor chosen by Sir Alan Sugar as the winner of the latest series of The Apprentice. He is backing her in a venture launching a chain of cosmetic surgery clinics.
"What message is this young woman projecting by her choice of business and what message is Lord Sugar giving by investing in this business?" said Mrs Heywood.
"Leah is a confusing role model. As a woman who has worked hard and excelled in her medical career and as a winner of The Apprentice, she has many admirable qualities and yet what she stands for and what she plans to do is far less admirable."