What the Gossip Girl Characters Would Wear in 2016

July 29, 2016

Friendship and fashion goals

You know you love them!

Can you believe it's been almost four years since the absolutely bonkers final season of Gossip Girl??? Lol, remember when, after six years of anticipation and theorizing, they revealed that Dan was the man behind the infamous blog??? Yeah, I was disappointed too (hands up if you had your money on Dorota!) but despite some of the ridiculous plot points, GG was the television obsession of my formative years. No wonder I have such high standards of living and a taste for luxury!

One of the reasons why Gossip Girl was such a cultural phenomenon? The fashion. While highly unrealistic for most teenagers, even wealthy Upper East Siders (though who wouldn't want to wear Marchesa to their prom?), the clothes were incredibly influential and helped to shape the trending styles of the late 2000s and early 2010s. For me, Blair's polished preppy style was the ultimate in #OutfitGoals, and I bought loads of colored tights and headbands in attempts to channel her covetable look. On days when I was feeling more free spirited, I looked to the effortless Serena van der Woodsen for inspiration. And when I indulged in the rare rebellious outfit, Jenny Humphrey was my fashion muse. 

Of course, fashion has changed a bit since the show's premiere in 2007 (Yeah, that's right; Gossip Girl started almost ten years ago, back when I was in the eighth grade! Feel old yet?) and I often wonder what the iconic characters would wear if the show began in 2016. 

So here we go! What the Gossip Girl characters would wear for a 2016 reboot:

Blair Waldorf

Blair always had a penchant for Ivy League style. Luckily for the Queen B, the classic prep is cool again in 2016. Blair would gravitate towards brands like Gucci and Miu Miu that mix heritage style with quirky eccentricity. She would have Kon Mari'ed her wardrobe to only include neutrals and primary colors. Pearls would figure heavily into her outfits but in unique ways, like on the heel of a Gucci pump or on one of her iconic headbands.

In the social media age, Blair would use her Gossip Girl fame to launch a lifestyle website a la Goop or Draper James, with a classic UES edge. She'd be the master of the flatlay.

Shop More Picks for Blair:

Serena van der Woodsen

As the free spirited socialite of the bunch, Serena would be very much into the 90s resurgence of late, specifically the minimalist glam of Kate Moss & Co. Her fashion influences would be Rosie Huntington-Whiteley and Gigi Hadid, although let's be real, Gigi would probably end up being inspired by S. Slip dresses in blush tones, swinging capes, and cool, handmade jewelry would all be staples of the 2016 Serena wardrobe. She'd still ooze sex appeal in brands like Balmain and Cushnie et Ochs, but it would be a little more restrained than her previous obsession with showing off her cleavage.  

Serena would obviously enjoy social media stardum and become a 21st century It Model like Gigi Hadid and Kendall Jenner. Blair would secretly compare followers with Serena and get annoyed every time Serena's follower count grew.

Shop Serena Essentials:

Jenny Humphrey

Jenny may not have been your favorite character on the show, but no doubt her style was unique. Who could have forgotten the episode where cheery, Blair-wannabe Jenny transformed to a racoon-eyed terror? Oh, Little J, we will never understand what happened to you. But I digress. Jenny would be pleased to see that her neo-punk style is all the rage again, with designers like Hedi Slimane and Alexander Wang featuring plenty of rock n' roll style. Jenny's wardrobe would feature a lot of Saint Laurent and Vetements, and of course, lots and lots of black. She'd be particularly excited about the return of the choker.

On the internet, Jenny would find her calling as a beauty vlogger. She would have every color of the Kylie Lip Kit and trade in her overdone eyeshadow for perfectly sculpted brows.

Shop Little J's Faves:

Which Gossip Girl character's style was your favorite?


  1. You NAILED IT with this post. I gravitate more towards Serena, but Queen B is equally fab.

    I think I need to go rewatch the entire show on Netflix -- I miss it!

    Natalie Was Here

    1. Aww, glad you liked it, Natalie! I feel like I alternate between the two. My hair says 'Serena' but a lot of my outfits are definitely more Blair. Thanks for reading!

  2. This is such a clever blog post!

    XO, Jessi

  3. thank you for some inspo


  4. This is such a cool concept for a post, and I agree that a big drawcard for Gossip Girl was definitely the fashion. Personally Serena's style was always my favourite but I definitely had a phase where I wore a heap of bow headbands to try and emulate Blair...


  5. Wow! Such an amazing and helpful post this is. I really really love it. It's so good and so awesome. I am just amazed. I hope that you continue to do your work like this in the future also Kinderjassen


I love hearing your thoughts! Thanks for reading! ♥︎Lindsey