Besides a few moments in the previous seasons, we are rarely given sights of Lily’s wild side: so far we have gathered different elements about her past, but I think it’s safe to assume she’s still largely mysterious and shady. She has totally embraced her Upper East Side persona, because it’s socially respectable, but we know she’s much more than that. I’m glad a glimpse of this was introduced in While You Weren’t Sleeping , the episode that was aired last Monday.
After failing his plan of being accepted by Russell Thorpe as part of the new Bass Industries, Chuck traces his steps back and asks Lily some help. I’ve always thought she loves him very much and she demonstrates it once more: she accepts of being part of a charade and pretends of still thinking of Russell. The central event of the episode is Eric’s birthday and, starting from these premises, it’s going to be a drama-filled party.
Before going out, she chats with Eric: in this scene, she wears a black satin with gathered neckline and a patterned pencil skirt; she completes the outfit with a ribbon necklace and diamond stud earrings.
Her necklace is a TomTom Jewelry piece – Forever May They Reign is the poetic name of this style: it’s 18K gold-plated decorations, vintage silk satin ribbon and ebony wood. It’s an original necklace, really beautiful, but I think wearing it on a black blouse wasn’t a very good idea.
The first step of the plan includes a row at a restaurant: they know Russell is there and they pretend there’s still troubles between them (Lily even slaps Chuck in the face).
In this scene, she adds a gorgeous black trench coat with a wide collar and a black bag to the outfit she previously wore.
As a loyal fan of her chic updos, here’s is a close-up on the one she sports in this scene: it’s pure perfection, since it incorporates a bun and intricate braided detail.
The fake row works its magic on Russell: he calls Lily and asks her out for lunch. Lily pretends she still has feelings for him; while she’s having lunch with her ex, Chuck is busy with finding information about Russell’s financial backer in acquiring Bass Industries.
I had some problems in identifying her bag but, thanks to the girls at the Purse Forum, now I know its designer: it’s a Boxer I bag by Reed Krakoff, made of caviar grain leather, with black nickel hardware. Its shape kind of reminds me of a Birkin bag, but this one is not as structured and has a more modern feel.
At the date with Russell, Lily explains her marriage is not happy and this somehow encourages him. For this reason, he shows up at Eric’s party.
I really love the outfit she sports in this scene: she usually wears neutral colours, so I’m glad she’s back to red, a clear symbol of drama . Before talking of the dress, let’s take a look at the accessories.
She wore Badgley Mischka crystal clip-on earrings, which have a beautiful oval shape.
She also wore a crystal bracelet, with a central element decorated by a star. Awww, this scene is so romantic! I love when Lily and Rufus are in cahoots: in this case, they pretend being unhappy with their marriage, but they take their chance to show they’re not.
Lily’s dress is a creation by Carolina Herrera and it comes from the CH collection. I love its scarlet shade, the patterned fabric and the feminine shape, emphasizing the hips and the waistline, accented by a ribbon belt. She wears a pair of patent Pigalle pumps by Christian Louboutin, which beautifully complement such a classic dress.
Again, her updo is stunning: she has ditched the bun she had in the first scene, and opted for a full-braided hairstyle. I love the incredible possibilities and variations of an updo we are given thanks to Lily; all the other characters never experiment with their hair, so it’s refreshing to see she’s the only one who always gives us something slightly different.
Lily and Chuck’s scheme is not completely successful, because Russell realizes Lily and Rufus are still going strong, but at least Chuck can talk to Thorpe’s backer about an alternative deal. What do you think will happen in the next episodes, besides the unexpected return of Dr. Van der Woodsen?
 The title refers to While You Were Sleeping (1995) by Jon Turtletaub, a super-romantic comedy starring Sandra Bullock and Bill Pullman.
 In The Townie, she wore two red dresses, not a coincidence because that was a pretty drama-packed episode for Lily’s story-line.