From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (3.15 – The Sixteen Year Old Virgin)

The Sixteen-Year-Old Virgin, the 15th episode of Gossip Girl‘s third season, is a juicy episode in a strange way. I think its fascination comes more from what it alludes to than from what is actually told and shown. The plot of Jack Bass and Elizabeth against Chuck is clear since the beginning, yet some questions about Elizabeth’s real identity still linger on. The same can be said for Lily, who makes it up with Rufus, but still doesn’t tell the truth about the relation to her former husband. The dismissal of the plot connecting Jenny and the bad boy Damien seemed a little bit too quick to me, but I’m sure the wild blonde girl will give us plenty to talk about in the next episodes.

At the beginning, Lily goes to Rufus to ask how things are going with Jenny. We can notice she’s back to her old self, with her hair styled in her trademark side-parted updo. I honestly miss her with loose hair, because she looked younger and more charming. It’s clear she wants Rufus back, so she returns to her style in full force.

The first thing I noticed when she entered the loft is her bag. I’m sad because she is not sporting her amazing Hermès bags in the show, but I must admit she is opting for lovely bags. This time she carried a Yves Saint Laurent Lover bag in brown. This is not my favourite YSL bag style (which is the fabulous bicolour Muse Two, seen on Miroslava Duma), but it perfectly matches her leather-trimmed brown coat.

Under the coat, she wore a gold top, peeking from under an Alberta Ferretti grey cardigan with embellished neckline, and black trousers. I really like this outfit, because it’s refined yet informal.

I’ve posted this screencap to show her updo, which is different from the messy bun she always sports. Love it!

The central event of the episode is the dedication of a museum’s wing to Bart Bass. Lily attends the event, of course, and she looks fabulous.

She wore a sleeveless Dries Van Noten Detroit dress, with a gorgeous floral/abstract print and an interesting draping at the neckline. She also carried a Judith Leiber saffron chain clutch [2] and wore gold clip earrings.

Don’t you think hairstyle in the first pic is different from the one in the second pic? The latter looks messier to me. In both pics, she is showing her love and affection to Chuck (awwww, how adorable was the moment when they hugged) and to Rufus. Rufus explains he has never cheated on her, and this is the moment in which they make it up.

Later in the episode, while she’s sitting in Rufus’ living room waiting for Jenny, we get a glimpse of her shoes – purple suede pumps. In the last scene where she appears, she is talking to her mother on the phone: they speak about health issues and medical tests, she’s quite worried, but it’s not clear whether Cece or Lily herself are implied. You know that Dr Van der Woodsen (played by William Baldwin) will make an appearance, so I guess we’ll soon get to know the truth. In the meantime, what are your impressions about this episode?

[1] The title, referring to Jenny, comes from the comedy The 40 Year Old Virgin (2005) by Judd Apatow, starring Steve Carell.

[2] The shape of the flap reminds me of Judith Leiber Grace bag, but it’s not exactly the same.





  1. Eccola!,la Lover! la YSL più sottotono che esista…
    Vabbe borsa a parte grazie per updo il coat è bellissimo,così come l’abbraccio a Chuck ,chi non l’avrebbe abbracciato così?,poor Chuck tua madre è un pò bitch meriti un bell’abbraccio…o forse quella morettona non è neppure tua madre…?.

    Aspetto ansiosa svilluppi nella trama,ma da quando ho visto nei promo Blair con quel cappello ho un pò di nausea…che sia un omaggio al cappellaio matto di Burton?.

    Un’ultima cosa: c’è qualcuno che veramente non conosce Dirty dancing? ti prego Super aspetta ancora 12/13 anni e poi provvedi con tua figlia!:-).

    1. Vero? Anche a me sembra una borsa tanto insignificante, ma nel contesto ci stava.

      L’abbraccio a Chuck, che dire? La morettona secondo me non è sua madre, anche il test del DNA è stato truccato, figurati! Per questo, penso che l’unica figura materna a cui lui possa fare riferimento è proprio Lily, che non è madre naturale ma che ha dimostrato diverse volte di volergli bene.

      Per Dirty Dancing, never mind. Essendo uno dei miei film preferiti, farò in modo che B lo guardi e lo apprezzi, quando sarà il momento, naturalmente 😉

  2. The gray sweater is Alberta Ferretti because it has the exact same embellishment as the AF top she wore in an earlier S3 episode.

    Also, her yellow purse is Judith Lieber!

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