3. Princess Anne at the Wedding of Lady Rose Windsor and George Gilman
The entire outfit, hat and all, was first worn in 1981 for Charles and Diana's wedding. Twenty seven years earlier. Anne's thrifty, and she's hardworking, and that's her schtick. But this?
Not only has this dress not aged well, it hasn't aged alongside its wearer. Perhaps, at the age of 31, Anne could pull off a dress with ruffles and flowers and netting. But in the years since, her public persona has become more honed, and putting herself in a dress that's downright girly these days looks silly.
Between this dress and Kate Middleton's solo presence at this wedding, the bride was hardly noticed. For shame.
Photos: Rex Features/Tim Graham/Getty Images