From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (2.16 –> 2.20 + Hermès Moment in Real Life)

One of my adult students at school is a big Gossip Girl fan, so we sometimes wonder what will come next in the episodes to come. He often tells me about the possible spoilers that appear on Internet, now and then, but I don’t give them credit, because I want to see what will be the real deal when the new stories are aired. Josh Schwartz, via Twitter, has recently given some interesting hints about we are about to watch:

1. Next 10 eps bringing the heat and headbands. All your fave couples (ALL…) getting lotsa screen time. Big finale. XOXO

2. The return of Dr VDW will have Team Humphrey vs Team VDW

The second is a reply to a question I asked him, because I wanted to know how things change with the return of Serena and Eric’s father. I also asked him if Lily would have more space, and the first sentence somehow answers this question.

In the meantime, writing about Lily’s outfits in the second season makes the month left before March 8th milder. Let’s start with You’ve Got Yale [1], one of my favourite episodes of the show. I like it so much because Lily is not a character which stays in the background (she often has this role, as the plot focuses on the young characters), but she’s truly a protagonist and plays an important part in the events occurring.

The opening scene is set in her kitchen, where she chats with Rufus, Dan and Serena. This is an important day for the kids because they will know if they’ve gotten into Yale.

Lily’s outfit is laid back and casual: she’s wearing a green satin top and a cashmere cardi, and diamond stud earrings only as jewels. Her hair is let loose with a side parting and the make-up is barely visible. This is a very muted version of Lily, but in the rest of the episode she will be absolutely fabulous. Please note the china set in the screenshot above: we will see it in The Debarted (3×12), too.

The second outfit sported by Lily first appears when Chuck goes to her apartment to ask her help. He is trying to remove his uncle Jack from the head of the company, but he hasn’t succeeded yet. When Chuck arrives, Lily is choosing the evening dress for the opera opening she will attend, later that day.

She’s wearing a stunning black suit, with a pencil skirt and a long-sleeved blouse with wide collar. In the screencap above we can also see a Verdura Maltese cross cuff bracelet around her wrist.

When Chuck and Lily  sit on the sofa in her living room, her shoes are visible: they are the lovely Miss Tack by Christian Louboutin, which she has worn in the previous episodes, too. I cannot help but adoring this style, so classic and lady-like!

In a scene set at the Bass Industries’ office, her outfit is more visible: she wears a belt on her blouse and diamond clip earrings. Her hair is styled in the trademark messy updo with side parting.

Lily attends the big night at the opera with Rufus, Serena and Dan (who are together again). What are your opinions about Chuck’s plaid coat? I usually love his flawless style, but I don’t really like this item on him.

The night at the opera brings some drama with it. Lily and Chuck meet her lawyer; during the meeting she remembers that before Bart’s death, they were to adopt each other’s children, so there are documents which could make Lily Chuck’s legal guardian. Chuck still hates Lily, because he thinks she has caused his father’s death, but he signs the agreement.

Lily has chosen a BCBG Max Azria satin dress, with a plunging and embellished neckline. Kelly Rutherford was pregnant during the filming of this episode, but the Empire line of the dress hides any bump. While she’s entering the powder room, she’s holding a satin embellished silver clutch.

If you have admired the Van Cleef & Arpels jewelry in the previous episodes, you’ll surely fall for the exceptional pieces she is wearing in these scenes. Folie de Pres is the name of the diamond earrings above, where each element has a different floral shape. Aren’t they perfect?

I seriously cannot describe with words the beauty and elegance of the bracelet she’s wearing: it is part of the collection Annèes Folles, is completely made of white gold and diamonds, and has an adorable tassel decoration.The picture above is not exact, because I couldn’t find a pic of the bracelet; in any case, its shape is the same as the ring from the same collection. I also love her hairstyle here – an updo with twisted bands, never seen on her before. You know I’m a hopeless NARSissist, but it looks like she’s holding a NARS lipstick in the screencap above, isn’t she? I own several lipsticks of this brand and I could spot their unmistakable shape anywhere. Unfortunately, I couldn’t find evidence that it actually was a NARS lipstick, but if so, what shade do you think she was wearing at the opera? My guess is Rouge d’Enfer.

When Jack realizes what has just happened – he’s out of the company because Lily is interim head of the Industries now – he attacks her in the powder room. Rufus and Chuck find them and Chuck knocks his uncle down. The day after, Lily invites Chuck to her place: she thanks him for the night before, and promises she’ll give him the company back when he is 18.

I often post pics of Lily’s living room because it’s a very beautiful room, full of interesting design pieces, such as the “scrunched” vase on the table behind the sofa or the glass centre-piece on the coffee table. In this scene, Lily is sipping tea from a white cup, and she’s wearing in black – a silk slip and a cashmere wrap sweater; the choice of dark colours is not incidental, as it mirrors her mood.

In Carnal Knowledge [2] – an episode in which Blair focuses all her rage against Miss Carr, her English teacher at school – Lily sports only two outfits. She is the head of the Parents’ Committee and for this reason she takes part into a meeting to discuss the accusations against Rachel Carr – Blair accuses her of having a relationship with one of her students, Dan.

For this event, she chose a very simple and laid back outfit. I couldn’t get a full-figure screenshot, but I guess she wore black trousers (or her trusty J Brand skinny jeans) with a green satin pussy bow shirt and a black cardigan. She also wore a statement piece of jewellery – diamantè earrings – and carried a flat clutch in black crocodile leather.

The second and last scene with Lily is set in her living room, where she’s discussing with Mrs Queller, the headmistress of the school. Queller has decided not to fire Miss Carr, after all, to avoid a wrongful termination suit.

In this case, Lily is wearing a brown shift dress, with short sleeves, pleats and a nice knot on the neckline. The shape of the dress is minimal, but she makes things interesting by wearing a lovely necklace, made of metal flowers. I don’t like this outfit very much, because I think it lacks life, but Lily looks lovely as usual.

The Grandfather [3] is an episode centred on the figure of William Van der Bilt, Nate’s grandfather, the patriarch of an important family, who wants to decide of his nephew’s social future. For this reason, the plot connecting Lily and Rufus is a pure filler, but still interesting. Lily is working with her art dealer and she comes to know that Rufus dated her some time before.

This scene is set in Lily’s living room: she’s working on her Apple laptop, and she’s wearing J Brand skinny jeans, a gorgeous Magaschoni sleeveless pink powder satin top and Christian Louboutin Miss Tack patent pumps. I love the embellished straps of the top and the crystal drop earrings. Lily looks beautiful when she’s wearing bright colours, but I think she looks stunning when she wears light or powdery colours, because they look incredibly refined and elegant on her.

When she pays Rufus a visit at the gallery, she tells Rufus about the art dealer and asks him if he has got other secrets he’s hiding. He suggest they could make a list with all their exes, so as not to have any secrets about their past lovers. Lily accepts, but she immediately regrets it.

In the scene at the gallery, Lily is wearing a brown collarless coat, with big black buttons on the front, and a grey knitted ruffled scarf; she carries her beautiful Kelly bag in Parchemin. Her hair is styled in an updo, as usual, but the bun looks like a knot, nice!

Trouble is around the corner, because Rufus has only a dozen lovers in his list, while Lily’s is endless; for this reason, she gives him only half of the real list she wrote. The truth will come out when Rufus opens her bag to tip the delivery boy of a Chinese restaurant. He is extremely disappointed and leaves, but later they make up.

Lily is worried while listening to Rufus, but it seems she cannot help but lying about her past. She has this same attitude all through the show (think of the infamous – but still mysterious – meeting she had with her ex husband in the third season), maybe because she finds it difficult to come to terms with the mistakes she made in her past relationships. In this emotional scene, she’s wearing a sleeveless black dress with ruffles on the neckline. The dress is uber simple, but the unhemmed ruffles give it a kick.

In Remains of the J [4] the action is focused on Jenny and Serena, who are both unhappy with their present lives. Jenny shows her rebellious side once again, when she sabotages a Sweet 16 party thrown by Serena and Lily for her, claiming she doesn’t want to be a Park Avenue princess; Serena suddenly realizes how boring her life is, after meeting her socialite friend Poppy, who is leaving New York to spend some time in Spain.

The first scene is set in Lily’s kitchen, where she’s making breakfast with all the members of her soon-to-be new family. Serena suggests some ideas for Jenny’s birthday party, but the girl explains she wants to keep things simple.

Lily is wearing a lovely Magaschoni Restaurant top in rusty silk with embellished and pleated neckline, but what I have immediately focused my attention on is her hairstyle. It’s been a long time since she sported something similar (in The Handmaiden’s Tale), and it’s a pity her hair is not styled like this more often, because it’s lovely. Her updo is more interesting thanks to a braid, while the bun is messy as usual. She’s also wearing hoop earrings with charms.

Jenny would like to spend a quiet night at home with her family, but things take a different turn: Serena arranges everything for a big party at her mother’s apartment, where things will soon get wild. When J realizes what really happened, she texts Gossip Girl and tells her there’s a rave party at the Van der Woodsens’. Lots of people crash the party and the police finally arrives to disperse them. Rufus and Lily get back home in the middle of all this.

I really like the outfit she has in this scene: she’s wearing a collarless coat, a tunic dress, black tights and her trusty Louboutin Miss Tack patent pumps (I really love them!). Her accessories are a diamantè cuff bracelet and matching earrings, and a nice green handbag, with a decorative embroidery on the flap.

Lily is furious and she accuses Serena of the chaos in her apartment. In the first screencap above, she’s holding the Matthew Williamson brown kaftan dress she wore at the Moroccan party at the Waldorfs in The Handmaiden’s Tale: someone must have taken it out of her closet. In these pics, we can see in detail the embellished neckline of her coat and the diamantè earrings she’s wearing.

She asks Serena to clean up the house and she spends the night at Rufus’ loft. The morning after, they discuss of a future together: Lily asked Rufus to move to her apartment and to sell his loft, so as to have the money to pay Yale’s tuition fees for Dan, but now they realize that maybe all these plans are untimely.

Lily’s nightwear is flawless: in this case, she is wearing an ivory silk pajamas and a beige cashmere cardigan, adorable.

When she gets home, she’s wearing the outfit of the night before, but her bag is different. From the screencap we don’t get a clear view of it, but it looks like a Nancy Gonzalez crocodile bag.

You know I love Lily’s style but also her refined taste when it comes to furniture and art. I’ve tried to identify the photo on the wall in the screencap above in any possible way, but no result. It immediately struck my attention because I’m sure it was taken on the backstage of Zac Posen spring/summer 2007 collection (I recognized the pink ruffled dress), but I still have no idea of which photographer actually took it.

Before closing the post, here is a magnificent Hermès moment Kelly Rutherford has recently given us. She attended the opening of the first Hermès Men’s Store in New York, on Madison Avenue, and showed off the latest addition to her massive Hermès personal collection.

She wore a sleeveless white dress with embellished neckline, black tights and black patent pumps, very much in Lily’s style. She only wore a black onyx cocktail ring and diamond stud earrings as jewellery.

She looked lovely, but I must admit my attention is all on the amazing Kelly bag she was holding. She already owns a 28 cm Kelly bag and we have seen it in Gossip Girl several times, but this one is brand new.

It’s a black 32cm Kelly Sellier bag with gold hardware. It doesn’t look very different from the other one, but the size is bigger. I also think this style is slightly different, because the Sellier is a very structured bag, with sharp edges. These are the details that distinguish it from the Kelly Retourne, which has a softer look and more rounded edges. I love all Kelly bags, but this Sellier looks heavenly.

What are your opinions about Lily’s outfits in these episodes? And what do you think of her new Kelly bag?

[1] The title comes from Nora Ephron’s You’ve Got Mail (1998), a successful romantic comedy starring Tom Hanks and Meg Ryan. The couple was protagonist of Ephron’s Sleepless in Seattle (1993), too.

[2] The title of this episode is also the title of a movie by Mike Nichols (1971), starring Jack Nicholson, Ann-Margret, Candice Bergen and Art Garfunkel.

[3] The Grandfather is inspired to Francis Ford Coppola’s masterpiece, The Godfather (1972).

[4] The reference is to The Remains of the Day (1993), a movie directed by James Ivory and based on a novel by Kazuo Ishiguro. Anthony Hopkins and Emma Thompson were the leading actors in the movie.

Source, source and source.




  1. I remember that we didn’t get to see a lot Lily’s clothes during this time because Kelly was pregnant. Thanks for these screen shots. She still looks great even while they were trying to hide her belly!

  2. Hi there!
    Thanks for always updating us on Lily’s style. You have a precise eye, and thorough research.
    I just realised that Down Under we are just this episode this week! Anyway, your screen caps help me with spotting details of Lily’s outfits each episode.
    Have a good week!

  3. Her hair is The Best. One could write an entire blog about Lily’s hair style, alone. The updo with twists is lovely and one I’ve never seen on anyone else, ever. Praise to the costume and hair & makeup departments on GG; I wish I could hire them to dress me once in a while!

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