From the Valley to the Upper East Side: Lily Van der Woodsen’s Style Cross-Over (4.18 – The Kids Stay in the Picture)

After a very long hiatus, Gossip Girl is back on track! I’m glad the comeback of my favourite tv show meant lots of drama and possible unexpected future turns in the narration. The Kids Stay in the Picture [1] wasn’t good only because some events of the previous episode developed (the relationship between Blair and Dan, Blair and Chuck, in particular), but also because it introduced new members of the Rhodes family, Carol, Lily’s sister, and her daughter Charlie. New characters always mean trouble, and Charlie is definitely going to change things in the plot, since Serena has already taken her under her wing.

The main event of the episode is a family photoshoot for a Taschen volume, Modern Royalty. This event brings the Humphrey/Van der Woodsen/Rhodes clan together, probably for the first time since the beginning of the show. Lily is desperately trying to keep herself busy: she knows the upcoming sentence is just around the corner, and the photoshoot looks like a good distraction.

In this episode, she changes four outfits, which means plenty of gorgeous clothes and accessories to write about. The first scene is set in her living room: she’s checking what the gossip site TMZ is writing about her. She’s wearing a romantic antique rose blouse, with ruffles on the front and ruffled cap sleeves; she pairs it with flared jeans.

In this episode, she sports two different updos: one of these is a classic chignon with her trademark side-parting.

I love her drop earrings, a statement piece which perfectly matches her black and grey crystal necklace. She wears Gerard Yosca resin rose quartz drop earrings with rhinestone posts.

The second scene featuring Lily is set at Intermix, the boutique where Serena and Charlie are shopping and where they meet their mothers. Carol has always struggled to raise her child far from the Upper East Side and its lifestyle, but Serena’s didactical shopping trip from Barneys to Intermix will crush Carol’s expectations.

Here, Lily pairs paired her flared jeans with a plaid coat by Dries Van Noten and with beige rosette pumps.

She also wears a mink scarf by Ralph Lauren, which gives the outfit a lady-like mood.

I’m not crazy about the bag she carries in this occasion. Even if the style is gorgeous – it’s the Keyhole tote bag by VBH – I don’t get why she didn’t wear a model in plain leather, but opted for a wool/tweed style with leather details. The leather version is definitely more beautiful than this one, which is actually cheap-looking, in my opinion.

The third scene featuring Lily takes place on the set of the photoshoot. I’ve been recently obsessed with the elegant curve-hugging style of Roland Mouret dresses, so I am glad she wore a creation by the British designer to give her own interpretation of “modern royalty” style.

In this scene, she wears a Myrtha wool-crepe dress in black, with folded details at shoulders, a triangular neckline and short sleeves. I think it’s flawless and she looks amazing in it.

Her accessories include Ippolita Lollipop 2-drop earrings. The pair above is made of clear quartz and gold, while the ones seen on Lily are made of onyx and clear (or is it smoky?) quartz.

In the jewellery department we can also find a Grande Dame ring by Henri Bendel, embellished with rhinestones and pearls.

In the picture above, you can see her updo (a French twist and Marcel waves) and her shoes (black satin pumps). She has a bag on her lap: it’s a croco-embossed leather bag with detachable strap, a style from the collection Kelly Rutherford designed for QVC. Though simple, it’s perfect to complete such a timeless outfit.

The fourth and last scene featuring Lily is set, again, in her apartment: she has a chat with her sister, trying to clear the shadows from the past that are still haunting them, but something unexpected is in store for both of them.

I’ve had a hard time in identifying the cute grey bow skirt she sports in this scene, and I think I’ve finally found it: it’s a flannel skirt by United Bamboo, with a bow at the waist and a lovely ruffled fold on the front. She pairs it with a front-buttoned grey sweater.

It’s rare to get a full figure of Lily, so it’s nearly impossible to see the shoes she’s wearing. This time I’ve been lucky because, while she’s sitting on the couch and talking to Carol, her shoes are visibile. Poznansa is s a gorgeous pair of open-toe pumps by Manolo Blahnik, made of snakeskin with jeweled t-strap.

Her jewellery consists in a pair of Belargo circle stone earrings and a dramatic crystal collar necklace. I still haven’t identified it, but I hope I’ll do in the future. As usual, if you have ideas about the unidentified items, please share them in the comments.

The episode closes with some unanswered questions. Why is Carol worried about her daughter, who has decided to stay in New York? Why does she ask Lily to constantly keep an eye on her? Will the arrival of Louis (Blair met him in Paris) affect things for Queen B? I must admit I secretly support a Dan & Blair option: they’re so different but cute together!

[1] The title comes from the documentary The Kid Stays in the Picture (2002), directed by Nanette Burstein and Brett Morgen. It’s also the title of the autobiography of the legendary Paramount producer Robert Evans which inspired the movie.





  1. I agree with you regarding the handbag in the shopping scene. That outfit has too much going on.

    IMO, the Myrtha wool-crepe dress is a real standout. It’s anything but a boring LBD. The length is lady-like perfect for her and I admire the neck and sleeve detail – sexy, but still a bit covered.

    I’m also very fond of the crystal collar necklace. This piece is so versatile and could be worn with so many things.

    Poor Lily, but exactly how many other criminals wait to hear about their sentencing while wearing jeweled snakeskin t-strap pumps? LOL!

    1. Exactly! I don’t like the bag but it’s even worse because it’s part of an outfit where’s too much going on.

      The Myrtha dress is amazing. I’ve recently been obsessed with this kind of dress (I’m looking for something similar, actually), I’m so lusting over it. Its the balance of details that makes it special – the lenght, the shoulders and the neckline. Gorgeous!

      Well, you know, she’s privileged in so many ways. Anyway, I think things will turn out well for her.

  2. I literally adore lily’s style and I’m disappointed because I can’t wear this kind of outfit. it isn’t just a budget matter but if I wear these kind of garments immediately I look like an old maid.

    1. I know! I could never wear her clothes either. I think it takes a slim body and a natural elegance (which I don’t have) to pull such a lady-like style off.

    1. Thanks for the tip! I checked their website and it looks like Lily’s necklace is not part of their collection. I’ll drop them a line, maybe I was wrong.

  3. I just want to congrats you for all the amazing lily van der woodsen posts.Since i am a huge fan of her style i am really happy i found out a site about her.I wish i could dress like her since she is always impeccable but when i try to dress like her i look overdressed and her hairstyles don’t really flatter me 😦 😦 guess you need to have a slim body and a natural elegance..still i am very much inspired by her style and how she ‘does’ jewellery!
    Her roland mouret dress is gorgeous and her earrings and make up flatter her..she looks like a true royal,Grace Kelly would be jealous!
    I also like her milky drop earrings and her coat…
    As for the last outfit i don’t really like her cardigan-top with buttons it seems too conservative and lily should not look conservative but classy and impeccable! i wish she could pair her skirt and necklace with a different top

    1. Hi! You’re welcome 🙂 I’m glad you like my posts about her!

      I’ve always admired her style, but I’ve never tried to dress like her, because I have a totally different figure (as you said, I think it counts) and vision of fashion, but still I think she’s one of the best dressed characters of a tv show.

      I agree: the Roland Mouret dress and the accessories she chose are pure perfection, somehow reminiscent of an old-style elegance.

      As for the last outfit, it’s true that cardigan is too plain and conservative, but I think it creates a balance with the skirt (classic but with a twist), the jewellery (the crystal necklace is a statement piece) and the jewelled shoes.

  4. I agree with classychicgirl her grey cardigan is kind of boring-conservative.I also miss her hermes moments,lily is an hermes kelly woman not random bags

    1. You are so right! She’s a Hermès woman, so I still cannot get over the fact she’s been wearing bags by other designers in the latest seasons.

  5. Hi,

    Thank you for all the fabulous details of Lily’s outfits. Just wondering do you know what brand her eyeglasses are? The cream ones that she wears throughout season 4?


    – p

    1. Thanks so much for your support.
      Oh, those glasses are a sort of obsession. I haven’t identified them so far, but it seems no one has done it either. Other sites have tried to identify them, with no luck. I’m sorry.

  6. Hello,

    I am still in search of Lily’s fabulous eyeglasses from Season 4. I am searching high and low with still no luck.. Have you managed to hunt them down yet?

    1. Sorry, but I still haven’t found them. I’ve just asked the question to Kelly Rutherford on Twitter. I hope she replies back. I will let you know 🙂

      1. No, I’m sorry.

        I’ve tried to ask Kelly Rutherford about these glasses (via Twitter), but I haven’t got any reply from her. I’ve also contacted Eric Daman, I hope he can give me more information about them. My guess is that they could be an old style by Alain Mikli, but I haven’t found any evidence yet 😦

  7. I enjoy this blog so much and thank you for all the hard work you put into it. I think Lily is one of TV’s most elegant characters and I’m surprised that more people/ magazines don’t write about her style. Kudos to the stylists working on Gossip Girl! I wish I could hire them to create a wardrobe suited to me (as many of you have pointed out, Lily has phenomenal style but it wouldn’t necessarily work for the rest of us “mere mortals.”)

    1. Thanks! I’m glad you’ve enjoyed my posts about her style. Well, people usually focus on the main characters of a tv series, but I prefer focusing on the ones that stay in the background, I think they’re more fascinating. Lily’s style is so flawless and elegant, it would be impossible for me not to write about it.
      I’m a bit disappointed by Daman’s style choices for some characters (Serena’s outfits in the 4th season, for example) but with Lily and Blair he’s always done an excellent job!
      As I wrote some time ago, I admire Lily’s style, but I wouldn’t like dressing like her: she’s flawless but ladylike, I have a more casual approach to fashion.

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