From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (5.21 – Despicable B)

Are you alive? Did you survive the huge amount of drama in Despicable B [1]? I had read some anticipations, but I had no idea things were about to go totally crazy. Lily’s fans must be happy with this episode, because she had lots of screen time, even if I’m sure not everybody is happy with the unexpected turn of the character.

The opening scene sees Lily and Serena leaving the court: a judge has invalidated Cece’s will and Lily is finally satisfied. It’s quite sure she paid Cece’s nurse to lie on Ivy’s behaviour during her stay with her mother, but we know Mrs Van der Woodsen is always ready to do whatever it takes to get what is hers. Serena and Lily meet Ivy, and for the first time the girl looks genuinely concerned about what Lily did; she keeps on saying she stayed by Cece’s side because she cared about her, and I think it’s the truth.

In this scene, Lily is wearing the outfit I wrote about some time ago – a blue trench coat, paired to a matching satchel bag and her trusty Ralph Lauren mink stole.

I’ve already posted it, but here we go again: this bag is so beautiful! It’s a Scottie small satchel bag by Mark Cross, a super-classy and refined bag which beautifully compliments Lily’s formal outfit.

Here she’s sporting one of her trademark updos – a knot-shaped chignon.

Later, Lily goes to Brooklyn to meet Rufus. There’s a change in his character, and I’m glad we are finally witnessing an evolution. Lily has changed a lot since the first season, while Rufus has been more or less the same, despite his move to the Upper East Side. Now, for the first time he is able to stand up for what he thinks it’s important to make a marriage work: he would like Lily to apologize for the way she treated Ivy, but she has no intention to retrace her steps, so she leaves without even opening the champagne bottle she has brought with her.

Here we get a rare full-figure shot of Lily. We can see her beautiful trench coat, worn with a pair of patent pumps.

Appearances and social status are probably the most important things for Lily, or things she clings to, because she doesn’t want to face her inner self and desires (this is my point). For this reason, she decides to organize a dinner party to dispel rumours about a possible split-up with Rufus and about a fight with Carol over their mother’s inheritance; the guest of honour will be New York Social Diary‘s David Patrick Columbia. In this scene, we can see what she was wearing under her trench coat – a Dolce & Gabbana leopard-print sheath dress. This dress is a bit out-of-place on her: she looks amazing, but such a bodycon piece is something that Serena – and not Lily – would wear.

I’m quite surprised by Serena’s behaviour in this episode: she doesn’t approve of her mother’s will to focus on social appearances and not on her problems with Rufus. I’ve never been a fan of Serena, but in this case she really shows that she cares more about important family relations than her mother.

Now we can also see her beautiful cuff bracelet in detail: it’s Bora Bora, a piece by Meghna Designs embellished with glass polki and cubic zirconia stones.

The reasons behind this dinner party are very different from what Lily told Serena. She has just found out that Lola’s father is William, her ex-husband, so now she’s finally found the reason to take her sister Carol down. Drama is on its way, so she calls Rufus and tells him the dinner has been cancelled.

She welcomes her guest wearing a beautiful black and white Lela Rose embellished dress, a piece which perfectly embodies her Upper East Side persona. She completes it with Jimmy Choo Lockett patent pumps (I love them!) and gold and black accessories.

Her necklace is by Rich Rocks – a chain necklace embellished with black crystals in several shapes.

She’s also wearing the East Lake cuff by Amrita Singh, made of 18K gold plated metal and resin stones, and a gold ring with black stones.

Here is Lily’s updo in detail, a chic take on the traditional low chignon.

During the dinner, all hell breaks loose: Lily tells Carol she knows the truth about Lola’s father and accuses her of being the mastermind behind Ivy’s fraud. The girl confirms that Carol asked her to play the role of Charlie (Lola’s real name), so Carol gets arrested. Later, Rufus pays a visit to his wife: they discuss and the problem of their relationship is disclosed again. Rufus tells Lily she sounds exactly like her mother, who would have done anything to preserve her family name, despite the consequences that this could have on the actual family members. Rufus realizes he doesn’t want to have anything to do with Lily, if this is who she really is. She replies: “Where exactly are you going to find some Upper East Side woman to take care of you like I have?”, but this is just the nail on the coffin: Rufus couldn’t care less about being an Upper East Side husband. I don’t know if they’re heading to divorce, but the relation is totally unbalanced (Lily thinks Rufus owes her everything from an economic point of view) and things can’t surely go on like this.

I’m kind of sad to see how things are evolving between them, but I’m glad he has finally become more self-confident and ready to face the future without his wife. As for the rest of the characters, I think the most important storyline deals with the real identity of Chuck’s parents. At the end of the episode we learn that his real father could be Jack Bass, but things are still not clear. As for Diana, the truth could not be so true: in the trailer of the next episode – Raiders of the Lost Art – she tells Jack: “Chuck thinks I’m his bloody mother”. This sounds like “I’m not his real mother” to me. What about you? And what do you think will happen between Rufus and Lily?

[1] The title is clearly a reference to the animated movie Despicable Me (2010) by Pierre Coffin and Chris Renaud.




  1. Fabulous recap, as always. I found it interesting to see Lily in the skin tight leopard print dress, so unusual for her. It’s like she has her claws out.

    1. It’s true: such an aggressive outfit was just an introduction to what happened at the dinner party. Unusual choice, but perfectly mirroring the situation.

  2. Yes – I agree with you about Diana. I do not believe she is Chuck’s mother. I didn’t buy her story when she explained it to him. OTOH, I wouldn’t be surprised to find out that Jack is his father.

  3. Regarding Lily, I think her strange actions are the result of her (not) dealing with her mother’s loss. IMO, they need a flashback or dream scene between her and CeCe that will help her come to terms with her mother’s death.

    1. I totally agree. It is as if she has never mourned her mother’s loss. And I also think that by accusing Ivy, she’s actually accusing herself of not being by her mother’s side when she was sick. I think she’s so mad at Ivy not only for the money, but because she reminds her of what she didn’t do for her mother.

      1. I agree 100%! Made the more poignant by the fact that Ivy wanted to help Cece out of kindness & not for money. (Ivy even rips up Lily’s $1M check).

  4. as it was mentioned previously – the leopard dress really does signify Lily’s ever present ferocious nature. It reminds me of Lily in season 2, when Jenny brought her and Serena their dresses and she tries on Serena’s body-con, slinky black mini dress. Perhaps anything on the sexier side reflects the Rebellious Rhodes, her hair hair down and relaxed, with tweed blazers and her knits are Lily Humphrey, and then her classic UES look signifies her as Lady van der Woodsen and a CeCe in the making.

    1. Thanks for your comment. Your analysis of Lily’s style is interesting, and I totally agree with it.
      I remember that black bodycon dress: it looked so out of place on Lily, but it clearly was a way to channel her aggressive side. Besides anything on the sexier side being a reflection of the Rebellious Rhodes, I think some “bohemian” outfits she sported in the first 2 seasons had the same function. When I decided to write about her style, I chose the title “…Style Cross-Over” because she actually experimented with the different sides of her personality (and the resulting fashion choices). At a certain point, this experimentation stopped: she ditched her bohemian outfits (and stopped carrying Hermès bags), and turned to a more conventional style, be it relaxed (as Lily Humphrey) or classic UES (as Lily Van der Woodsen). I love most of what she wears, but I really miss the old times: now her inner complexity can rarely be seen reflected in her style choices.

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