I’ve explained many times the reason why I decided to write about Lily’s outfits – and not Serena’s or Blair’s – in Gossip Girl: I love her refined style, but I also think her character is much more complex than what it looks like, and Petty in Pink  (the 19th episode of the 4th season) proves it. This is a drama-packed episode, with several narrative lines going on at the same time – Raina, Chuck and Nate looking for the girl’s mother; the weird triangle Dan/Blair/Louis; the rivalry between Blair and Serena.
In the opening scene, Lily is busy with shopping online and with trying on items that have just been delivered. She can’t go out shopping because she’s under house arrest. In the first part of the episode, she behaves as the old same Upper East Side lady we know well, but there’s an interesting twist in the character in the second part.
In this scene, she’s wearing black wide pants and a nice short-sleeved cable-knit cardigan, with a scarf as collar.
While she’s putting a pair of ankle booties on, we can get a glimpse of her jewellery. She’s wearing three bangles and a lovely flower ring, which totally reminds me of the infamous Auction flower ring by Ramona M. Boucher of Bastion, featured in Sex and the City – The Movie.
In the screencap above, here is Lily’s perfect bun. In the second scene where she appears, she’ll opt for a very different updo.
Later in the episode, Anne, Nate’s mother, pays her a visit to discuss about the upcoming Pink Party in support of the breast cancer awareness. They’re supposed to be friends, but we will learn how things are very different from what they appear to be. Lily wants the party to be held in her apartment, and the intervention of a blackmailing Serena makes her wish come true.
At the party, she looks stunning in a long, one-shoulder pink taffeta dress, even if – I must admit – the best dressed of the event was Blair, who wore a fantastic Oscar de la Renta ombré strapless dress.
Lily is at the centre of the attention, not only because she’s the hostess of the party, but because of the harsh criticism of her (supposed) friends. Anne speaks her mind, telling her many people will be happy to witness her downfall and social decline.
Lily’s pink dress is a creation by Redux Charles Chang-Lima, embellished by flat ruffled details at the waistline and shoulders.
I love the graphic backline: the back is naked but for a single strap. In the picture above, her updo is visible: it’s a little bit too matronly and backcombed for my liking but it perfectly suits such an important dress.
As I mentioned before, in the second part of the episode Lily changes attitude: she realizes her friends are not supporting her, but are talking behind her back. For this reason, she pretends she doesn’t know she can’t leave her apartment (she’s wearing an ankle bracelet), waits for the police to come and asks them to shut the party down.
She hasn’t done anything particularly rebellious, but in this case it’s nice to see like her wild old ways come out in difficult moments. In the pic above, we can see her hot pink patent peep-toe shoes and her ankle bracelet, which oddly looks like a Rado watch.
This season’s finale is slowly coming, so I guess we’ll soon learn more about Lily’s destiny. Any predictions?
 The title comes from one of my favourite movies, Pretty in Pink, directed by Howard Deutch in 1986 (the screenplay was by John Hughes), featuring the best love triangle ever – Andie (Molly Ringwald), Blane (Andrew McCarthy) and Duckie (Jon Cryer).