From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (2.11 –> 2.15 + On the Set)

I’m writing this post after hearing some good news about Gossip Girl: the next episode will be aired on March 8th, Dr Van der Woodsen (William Baldwin) will finally appear in the show, some bad drama is coming for Lily and Rufus, and for Chuck and Blair. I cannot hide my impatience for what will come next, but in the meantime, let’s go back to the second season, to admire Lily’s flawless outfits in detail.

The Magnificent Archibalds [1] opens with Lily and Bart returning home from a week-end out.

She’s wearing a black top and an elegant grey suit – a double-breasted short jacket with black details and a pencil skirt – and she’s toting her trusty Hermès Kelly black bag. Her accessories are a black beaded necklace, tiny diamond stud earrings and two diamond rings. The opening scene introduces part of the episode’s drama: Rufus has just found out that Jenny is staying at Lily’s with Eric, and he asks Lily to speak to his daugher.

Lily and Rufus meet by the Hudson to discuss the possible ways to convince Jenny to go back home. In this scene, Lily is wearing a casual yet lovely outfit – a Brunello Cucinelli cashmere coat, a grey wool scarf and black trousers. She’s also wearing the Alhambra mother-of-pearl and white gold earrings by Van Cleef & Arpels which she wore in the first season.

If you often read my blog, you’ve surely noticed that I love the so-called Hermès moments in Lily’s outfits. What is stunning is that all the H pieces spotted on the character are actually possessions of Kelly Rutherford. In this case, she carries her 35 cm Birkin bag in Gold ostrich leather with palladium hardware and wears a Cape Cod watch with strap in Etoupe leather.

Later in the episode, Lily and Jenny meet, but more drama is around the corner: Lily has found some emancipation papers in Jenny’s bag and invites Rufus over to confront his daughter.

In this scene, she’s wearing a grey cashmere long sweater with cowl neck, skinny jeans and tan boots, an outfit perfect in its simplicity.

One drama at the time is not in Gossip Girl‘s style; for this reason, Eric and Lily find out some secret dossiers about them and Serena in Bart’s safe. When Lily realizes what her husband has done to her and her family, she confronts him and leaves with her children.

This is an important scene because it will lead to fundamental events in the following episodes. Here Lily is wearing a Hugo Boss brown silk dress with a ruffled decoration on the bodice and Christian Louboutin Simple pumps in cream.

She also wears gold and citrine drop earrings and sports her trademark hairstyle, a low messy bun.

Since it’s Thanksgiving, Lily decides to crash Rufus’ dinner. This is the second time they spend Thanksgiving together.

When she and Eric arrive in Brooklyn, she’s wearing a beige trench coat and carrying her amazing Hermès Kelly bag in Parchemin. The episode seems to have a happy ending, but Bart’s darkness is spreading its wings again: he has discovered Lily was hospitalized some years before and now he wants to know exactly what happened.

It’s a Wonderful Lie [2] is possibly one of my favourite episodes ever, because the atmosphere at the Snowflake Ball (the main event of the episode) is romantic and magic and because things between Lily and Rufus/Blair and Chuck are getting more and more interesting. Lily is busy with the preparations of the ball, but Bart comes over and confronts her.

She’s wearing a fitted velvet jacket, a black top with purple satin bow, J Brand skinny jeans and Christian Louboutin black pumps. In this scene she gives us the first and only Hermès moment of the episode, because she’s carrying her Kelly bag in black. Maybe it’s because of the different colours and fabrics in this outfit, but I love it so much!

Bart apologizes for his behaviour, but Lily explains she’s not ready to forgive him yet.

In the screenshot above, Lily’s earrings are visible: she’s wearing Verdura three-stone earclip earrings in yellow gold with diamonds and rubies. I must admit I was a bit surprised when I found out that Verdura brand is still on the market. I’ve always admired the magnificent and visionary pieces by Fulco di Verdura, the legendary Sicilian aristocrat who collaborated with Coco Chanel and designed the infamous cuff bracelets with the Malta cross on them, but I ignored that his legacy hasn’t been forgotten.

Both Lily and Rufus attend the ball and they spend most of the time together. The setting of the party is magical, with all those crystals and white trees and lights. When they dance, the peak of romanticism is reached.

This is truly one of Lily’s most memorable outfits, even better than the magnificent look she had on her wedding day. She’s wearing a white dress with asymmetrical straps and stunning diamond jewellery, enough to make me sigh with appreciation. Her hairstyle is lovely, too: her ordinary updo is made special by twisted locks, pinned one next to the other.

The dress is a Vera Wang creation from the spring 2009 bridal collection. The dress seen on Lily has been slightly modified – a ribbon belt has been added.

When it comes to jewellery, Lily has a soft spot for Van Cleef & Arpels: in this case she sports pieces from the Snowflake collection (the name of the collection is the same of the event she’s attending!). In the screenshot above we can see her drop earrings in platinum and diamonds in detail.

She also wear the  bracelet in platinum and diamonds from the same collection, which she wore on her wedding day.

At the ball, just before receiving a phone call about Bart’s fatal accident, we get a glimpse of her Salvatore Ferragamo Musa clutch in satin with diamante clasp, the perfect accessory for such an amazing outfit.

Bart’s death will leave its sign on most of the characters of the show; for this reason, O Brother Where Bart Thou? [3] is one of the most dramatic and dark episodes of the second season. Chuck will go through a downward spiral of self-destruction, while Lily will face some ghosts from her past.

In the opening scene, she’s facing her husband’s passing away in Lily’s way – making lists and planning her and her family’s day. It’s clear she is not really mourning Bart, because she has never loved him and was planning to leave him at the time of the accident. When she leaves home, she meets with Rufus in Central Park (another romantic moment) and they decide to leave for Cornwall just after the funeral.

During their romantic stroll in the park, we get a rare full-figure shot of Lily. She’s wearing a grey pantsuit and sweater, an ombre brown/grey fringed scarf, brown boots and her Hermès Birkin bag in Tobacco ostrich leather. The only jewel she’s wearing is an amber beaded necklace.

At the funeral, Chuck is desperate and completely out of control. He accuses Lily and Rufus (through Dan) to be the cause of his father’s death, and we cannot blame him for his distraught behaviour, so much that he knows Lily’s secret (now it’s clear this refers to Lily and Rufus’ child).

At the funeral, she wears a Brunello Cucinelli cashmere coat (the black version of the one she wore in the previous episode), black leather gloves, a black dress and her Kelly bag in black. In this episode, her hair is always loose, with a side parting.

At the funeral party at her apartment, Lily is impeccable, wearing a sleeveless sheath dress with jeweled neckline. It looks like everything has finally become easy for Lily and Rufus, but one last sensational moment is on its way: Cece, Lily’s mother, tells Rufus about her daughter’s secret and this crushes the couple’s plans for a getaway. Rufus goes to the Central Station not to leave with Lily, but to ask her an explanation.

At the station, Lily sports a casual but refined outfit, wearing an aubergine sweater, black cropped jeans and a beige trench coat. She cannot but travel in style, wearing Lanvin black patent flats and carrying a Gucci monogrammed rolling suitcase.

In the Realm of the Basses [4] is the fourteenth episode of the season, where the subplot connecting Lily and Rufus is brought further. After knowing Lily’s secret, Rufus wants to find their child, but Lily is not ready to follow him. When she pays a visit to the gallery, she refuses to give Rufus details, she only says it’s a boy.

This and the following episodes will show a different side of Lily’s personality (and style): the recent loss of Bart and the return of a ghost from the past seem to have taken a toll on her. She is dressed in black or in dark colours, preferring loose-fitting clothes and soft materials. We know Eric Daman opted for this change in her style because of Kelly’s pregnancy, but it actually mirrors the rough moment the character is going through. In this scene at the gallery, she’s wearing a black coat and a scarf, and she’s sporting a new hairstyle, a half-updo never seen on her before.

A gold woven cuff and Verdura caged clip earrings in gold and cocobola wood complete this austere outfit.

Later that day, Rufus goes at Lily’s apartment, where he tries to convince her to find their son. Lily is full of fears and doubts, but she finally agrees, because giving her son up has always been like a heavy weight on her heart.

I love the outfit she’s sporting in this scene, because it is simple, casual and neat. She’s wearing J Brand black cropped jeans, a John Patrick Organic belted wrap cardigan, a lovely Tory Burch pleated top with tiny embellishments on the neckline and a magnificent pair of Christian Louboutin Miss Tack pumps. I am a fan of Louboutin stiletto heels and crazy models, but I think this style is the best: the round toe is so romantic and the not-so-high heel makes it pure perfection. I don’t own any Louboutin shoes, but, could I choose one pair to own, I would choose this one, because I’m 100% sure I’ll actually wear it all the time.

The only accessory she is wearing is a pair of Verdura clip earrings with diamond and gold cages. The earrings pictured above are not the exact ones on Lily, but they are very similar.

The episode closes with Lily and Rufus leaving for Boston. In this case, she only added a black coat to the outfit above.

Her luggage is made of a black shoulder bag and a carry-all.

Gone with the Will [5] deals with the long-awaited reading of Bart Bass’ will (who left 51% of his industries to Chuck) and with Lily and Rufus’ trip to Boston to find out more about their child. Even if this is something they would like to keep secret, it soon becomes public. Once in Boston, they visit an adoption office, but it’s still unclear whether they’ll actually meet their son or not.

In this scene, Lily is wearing a conservative black dress, Christian Louboutin patent pumps and a grey coat. Her hair is styled in an updo as usual, and the accessories are minimal.

The dress she’s wearing is an ADAM piece, with a gold beaded neckline.

While she’s sitting in the office, we can get a glimpse of the bracelet she’s wearing around her wrist: this is a Kara Ross five-stone X cuff in gold and lapis-lazuli. I’ve never liked the shape of this bracelet, but it nicely completes such a severe look.

After the visit at the adoption office, they go back to their hotel and are ready to leave for New York, when they receive a phone call from the adoptive parents of their son, who eventually agree in meeting them. You’ll remember that they will leave Boston thinking their son is dead, which is not the truth.

In this and in the following scenes, Lily will sport a casual and cozy outfit – skinny jeans, a grey shirt and a dark grey cashmere wrap sweater. Here her hair is loose and she has no jewels on. This is a very muted version of Lily, but I guess it depends on the circumstances of the episode.

Before closing the post, here are a couple of candids from the set of Gossip Girl. All the actors are filming new episodes, including Kelly Rutherford, who was spotted in the streets of New York sporting two lovely outfits.

Back in September 2009 she sported a very similar outfit, but I personally never have enough of the amazing Hermès moments she gives us. In this case, she paired a casual hooded puffer coat with skinny jeans and a wrap belted cardigan. She was carrying her trusty 30 cm Birkin bag in Etoupe and wore her Jumping boots in black. These pieces are so timeless that I would wear them all the time, like Kelly does.

This candid was shot between the takes, because Kelly was wearing comfy Ugg short boots. I love the rest of the outfit, which includes a a beige-trimmed white belted coat, a beautiful turquoise cuff bracelet and a bag never seen on her before. It is the Marcello bag by Cartier: the one on Kelly is made of white buffalo leather. I love the shape of the bag, so classy, and its inspiration, one of the most famous and talented Italian actors ever, the one and only Marcello Mastroianni, protagonist of Federico Fellini’s masterpiece, La Dolce Vita (1960).

Other posts on Lily’s style are on their way, so don’t forget to check back soon!

[1] The title is inspired to The Magnificent Ambersons (1913), a book written by Booth Tarkington which won the Pulitzer Prize in 1914. The story in the novel is related to this episode because it tells the declining fortunes of three generations of the aristocratic Ambersons. The novel became a movie with the same title in 1942, directed by Orson Welles, starring Joseph Cotten and Ann Baxter.

[2] The reference is to one of Frank Capra’s most popular movies, It’s a Wonderful Life (1946), starring James Stewart and Donna Reed.

[3] The title refers to O Brother, Where Art Thou? (2000), directed by Ethan and Joel Coen, starring George Clooney, John Goodman and John Turturro. The movie, set in Mississippi during the Great Depression, is loosely based on Homer’s Odyssey; its title comes from The Tempest by William Shakespeare. The eighth episode of The Simpsons‘ twenty-first season has the same title as the Gossip Girl episode.

[4] The title is inspired to the erotic Japanese movie In the Realm of the Senses (Ai No Korida), directed by Nagisa Oshima in 1976.

[5] Gone with the Will is clearly inspired to Gone with the Wind (1939), the epic movie directed by Victor Fleming, starring Clark Gable and Vivien Leigh.

Source, source and source.



    1. Serena is perfect in that outfit, one of the best ever.
      Btw, her jewelled trench is by Burberry Prorsum.

      I’m glad you have my same opinions about Louboutins. I mean, the high-heeled styles are gorgeous, but I think it takes “something” more (say class – and I’m referring to Lily) to choose one of his mid-heel styles or flats. Every celebrity sports Louboutin’s towering heels, because they’re IT shoes, but not so many opt for different – but equally lovely – styles.

  1. Thanks so much for giving us a little Gossip Girl style while they are on hiatus. I love looking at these past outfits because I am always amazed at how great Lily looks!

    1. You’re welcome 🙂

      I love writing about Lily’s style, because it never lets me down. Her past outfits are amazing, but I must admit I am soooo looking forward to what will come in the next episodes. Gosh, I wish March 8th was today!

  2. Thanks again your wonderful posts!

    BTW, Lily’s jeans in It’s A Wonderful Lie and In the Realm of the Basses are both J Brand.

  3. Thank you so much for your in-depth analysis of Lily’s style. I’m a big fan of Hermes and love to see how her character interprets the look. It’s also refreshing to see discussion of Lily’s style, when often the focus is on Serena, Blair, etc.

    1. You’re welcome 🙂

      Since the beginning of the show I have thought Lily’s style is the best, because she is always true to her self, without paying much attention to the current trends. The younger characters dress according to what is trendy, but Lily is above all the fuss. And then her Hermès moments are always amazing.

      As a fan of Hermès, do you own anything of their lines? One of my dreams is owning a Kelly (which I probably will never get), but I am pretty much happy with a H silk carrè scarf I bought some years ago 😉

  4. I think Eric Daman does a masteful job of reflecting each of the characters through their wardrobe.

    I also have a Kelly on my wish list. 🙂 I own several scarves and the Cape Code PM. I also wear 24, Faubourg every now and then.

    1. I don’t wear watches…but the Cape Cod is lovely! What colour is the strap? Lily’s watch with the strap in Orange Potiron is to die for!

      I have never tried 24, Faubourg, but my mum has always used Caleche and I must admit I like it. Ok, I’m a hopeless Diptyque addict, but Caleche is a classic.

      Eric Daman has done a terrific job with all the cast. I don’t like Blair’s style change in the third season, but in the first two seasons all her outfits were flawless.

  5. I’m glad I’m not the only one who was bowled over by lily’s purple blouse/black velvet blazer/ black kelly bag outfit. It could look prim and silly with that big floppy bow at her neck but instead it looks fun, elegant, appropriate and current.

    I don’t even care about her jewellery. It’s lovely but honestly, it’s the clothes and bags I covet.

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