Penelope Featherington (Lady Whistledown) From Bridgerton
What to wear:Penelope Featherington (aka Lady Whistledown) knows all, and despite being an unsuspecting observer of London's elite, she isn't afraid stand out with her fashion. To dress as London's top gossip writer, Penelope wears colourful floor-length frocks that match her sparkling jewellery. Her red curly hair is a staple as Penelope almost never blends in — the bolder, the better!