From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (1.12 –>1.17)

When it comes to my favourite tv show, I still haven’t found the time to watch some episodes from the first two seasons again, but my holidays end on January 8th, so I’ll try to do it.

Let’s start from where I stopped last time, with School Lies [1], the twelfth episode of the first season. In this episode, it is clearer and clearer that things between Lily and Rufus are becoming complicated. Lily’s heart is with her true love, but social conventions have forced her in Bart’s arms. In the first scene in which she appears, she goes to Rufus’ gallery to tell him she’s accepted Bass’ wedding proposal.

In this case, she’s wearing a classic camel coat and a white pussy bow blouse. Unfortunately, I couldn’t get a full-figure screenshot, but it can be assumed she is wearing skinny jeans under the coat.


The following scene is set in Lily’s apartment, where Rufus asks her to leave Bart and to choose him. Lily is lost, she doesn’t know what to do, but later in the episode she’ll make her mind up.In this scene, she’s wearing a nice beige satin chemisier, with black buttons on the front and two side pockets. She also sports tiny diamond stud earrings and a black bead tassel necklace.

She takes her decision during a boring lunch with Bart. While her soon-to-be husband is taking a phone call, she calls Rufus and tells she wants to be with him. In this scene, she’s wearing a gorgeous beige dress with 3/4 sleeves and a cowl neck. I love her dangling earrings with round flat pearls. You may have noticed she’s wearing lots of beige clothes in this episode, and I think this is one of the colours which suit her best.

She’s taken her decision, so she starts packing for a weekend away with Rufus. Things suddenly change because Serena asks her mother not to choose Rufus, because she doesn’t want to become Dan’s step-sister (we all know this will happen in the third season). In this scene, Lily is wearing another pussy bow blouse (this time it’s purple) and brown tailored trousers.

A very sad scene occurs when Lily tells Rufus she has changed her mind, without explaining the real reason. Lily is not playing fair, but her style is impeccable as usual. I think this is the best outfit of the whole episode, so romantic (and this contrasts with the moment). She’s wearing flared trousers, an ivory silk blouse with a massive bow (I adore it) and a military-style jacket.

The last scene is the engagement party of Lily and Bart. It’s evident she’s not happy at all, but she grins and bears it. She’s wearing what it could be assumed is a dress, with a tulle layer and a turtle-neck. I love her pearl earrings, simple and absolutely perfect for this slighly funereal dress.

The Blair Witch Project [2] is an episode all based on Jenny’s first attempts to take Blair’s role of Queen Bee, so the rivalry between the two is about to begin. As for Lily, she has just come back from a trip abroad with Bart and she’s busy with the wedding preparations.

She appears in three scenes. In the first, she’s having breakfast, wearing sunglasses (to hide the dark circles under her eyes) and a comfortable Tomas Maier sleeveless dress, with gatherings on the shoulders; she’s also wearing pearl earrings.

During a brunch with her family (including Dan), she sports a gorgeous dress by Tory Burch, made of metallic fabric, with the jeweled neckline and white inserts on the neck and on the cuffs. In this scene she gives us another Hermès moment, because she’s wearing a Kelly Double Tour bracelet in white leather. This bracelet revolves twice around the wrist (just like the Cape Cod watch) and has a closure similar to the Kelly bag’s.

Serena’s character is about to have lots of trouble, because her nasty friend Georgina is back in town. She is looking for her mother’s support, but Lily is too busy with the wedding preparations to help her. I love Lily’s character, but she is sometimes an absent parent, because her mind is often somewhere else. Oh well, we all have our faults, haven’t we?

In this scene, set in Bart’s living room, with a magnificent view on New York, Lily is wearing a black and white printed dress by Thread Social. It’s an unusual dress for her (that frill running along the hem is not part of her style), but she sometimes likes experimenting and wearing flirty dresses.

All About My Brother [3] is one of my favourite episodes, because it’s full of drama and of romanticism. The upcoming wedding is totally occupying Lily’s mind, but some shocking news about her son (Eric is gay) are on their way.

We first see Lily leaving her apartment, busy with the wedding planners, and meeting Rufus outside the courtyard. Rufus asks her help because he doesn’t know what to do with Jenny, who has lied about a party she’s planning. Lily asks him to go with her to Vera Wang, so they can talk about Jenny on their way there. In this scene, Lily is sporting a very Prada-esque outfit: she’s wearing a Diane Von Furstenberg green skirt, a Dolce & Gabbana flower-printed blouse and a collarless beige jacket with black trim by the same designers. She is also wearing eye-glasses and carrying her trusty black Kelly bag.

I love love love this scene, set at Vera Wang’s atelier [4], when Rufus sees Lily wearing her amazing wedding gown. I will write about this dress in an upcoming post, but let me say it is beyond gorgeous and Lily looks flawless. Their side-to-side reflection on the mirror is so a romantic moment! They are so in love with each other, but they are star-crossed lovers at this time of the story.

Georgina means drama in the show, so it’s not coincidental she will throw Eric out of the closet at a dinner with the Van der Woodsens. In this scene, Lily is wearing a bright blue sleeveless dress, paired with a belt with a big gold buckle (it’s not clear if this is a Hermès piece).

She’s also wearing Van Cleef & Arpels gold and mother-of-pearl earrings from the Magic Alhambra collection. In the following episodes she will always sport Van Cleef & Arpels stunning jewellery, always perfectly matching her outfits. In this case, these earrings add a playful touch to a very simple outfit.

In the last scene, she Lily apologizes to Eric for her shocked reaction to his being gay, but she explains she’s scared and would like to protect him from the difficulties he may encounter. Here she’s wearing a short-sleeved black robe and a satin night-dress, with lace on the neckline.

In Woman on the Verge [4], the drama of the previous episodes, connected to Georgina’s comeback in Serena’s life, explode. Serena’s secret (she did some lines of coke with a man, who then overdosed and died) is resurfacing and this is adding tension to tension. Lily is preparing her wedding, but things are not smooth as they seem.

In this episode, she appears in three scenes. In the first of them, she’s sitting in her living room with the wedding planner.

She’s wearing J Brand skinny jeans, a grey printed blouse and a nice collarless cream jacket with silvery accents.

She also wears Tara tahitian pearl earrings, from the Vintage Collection. 

When she leaves her apartment, we can see the bag she’s carrying, a Chanel crocodile-quilted 2.55 reissue bag in dark purple. The bag is part of the Fall 2007 collection and, if I’m not mistaken, is made of jersey. The double strap includes a chain and a jersey strap. I’m not a fan of this style because I prefer the classic 2.55, but it’s a nice colourful version of a timeless bag.

More drama happens at Lily and Bart’s party to celebrate their wedding. Lily knows Serena’s secret and confronts her daughter about this, threatening to send her away of the party. When Serena breaks down and leaves, Blair asks Lily to follow her daughter, because she desperately needs her support.

For this event, Lily chose a very conservative dress, a little black number with ruffled shoulders by Alberta Ferretti. The dress seen on Lily is a modified version of the dress seen on the Fall 2008 runway.

Her dress is simple, and the rest is simple, too. Her hairstyle is her trademark updo (this time, the bun is similar to a knot), and her jewellery is small and not showy. Lily is a fan of Van Cleef & Arpels jewellery: this time she is wearing two pieces from the Alhambra collection – a pendant and earrings in white gold and mother-of-pearl.

The final scene of the episode is a bomb, because it emphasizes the idea that the upcoming wedding could be in trouble. Lily finds Serena in a club where Rufus and his band are performing. After the show, he chases after her and asks her to stay with him. This time she doesn’t resist and the two finally kiss.

In this case, Lily is wearing a Burberry double-breasted trench coat in Jet, a classic piece which perfectly suits Lily.

The next post about Lily’s style will be entirely devoted to the eighteenth and final episode of the first season, so check my blog soon for updates!

[1] The reference of the title comes from School Ties (1992) by Robert Mandel, starring Brendan Fraser, Chris O’Connell and Matt Damon. This movie is about a Jewish boy goes to an elite prep school in the 1950’s and hides his religion until a jealous school-mate forces it out in the open.

[2] This time the screenwriters didn’t use their fantasy, because the title of this episode is the exact title of the infamous movie by Daniel Myrick and Eduardo Sanchez, released in 1999.

[3] This is of course a reference to All About My Mother (2000) by Pedro Almodovar, which won an Oscar for best foreign language film.

[4] This scene at Vera Wang’s atelier can remind of the scene in Sex and the City (the episode is Don’t Ask, Don’t Tell, 3×12), when Miranda, Carrie and Samantha go to Vera Wang to try their bridesmaid dresses for Charlotte’s wedding. Charlotte chose her dress at the same atelier in Running with Scissors (3×11).

[5] Here comes another reference to another Pedro Almodovar film, Women on the Verge of a Nervous Breakdown (1988).

Source and source.

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11 comments

  1. Thanks for the fashion flashbacks!

    Lily’s first outfit in All About My Brother: Jacket is Dolce & Gabbana; Skirt is Diane Von Furstenberg

  2. Some more IDs: Her jeans in Women on the Verge are J Brand and the blouse she wears with the beige Dolce & Gabbana jacket is also Dolce & Gabbana

  3. It’s fun seeing her in the Threads dress, since she’s usually in more serious and authoritative clothes. This dress makes her look a little more youthful and playful.

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