Fashion critic Mr. Blackwell died recently. From 1960 to 2007 he released a yearly list of the world's Worst Dressed Women. Over the years, several royal women topped the list. I managed to find some photos of them during the years in question:
1965 – Princess Margaret (Photo)
1969 – Queen Elizabeth II (Photo)
1982 – Princess Diana (Photo)
1985 – Princess Stephanie of Monaco (Photo)
1988 – Sarah, Duchess of York (Photo)
1994 – Camilla Parker Bowles (who later became Duchess of Cornwall). I couldn't find a photo of her in 1994.
In recent years, the likes of Paris Hilton and Britney Spears have come along to take the heat off the royals.