The Most Fashionable Looks on Gossip Girl

Gossip Girl orignially aired in 2007 and centers around the teenage drama of the Social Elites of the Upper East Side. The iconic characters within the show include Serena Van Der Woodsen, Blair Waldof, Nate Archibald, and Chuck Bass. Other than the story behind the television show, it became very accredited for its iconic outfits. The daily life of the Upper East Side elite, main characters’ style and fashionable looks were designed by Dior, Chanel, Gucci and many other incredible designers. As each character has their own personality to go with their style, there is a unique fashionable look in each episode. In celebration of the reboot of the show, announced by HBO MAX, let’s recap the most memorable looks from Gossip Girl!  

  1. 1. Season One, Episode One – Serena

    In the first episode, we already have a surprise with the “I am back” Serena Van Der Woodsen outfit. 

  2. 2. Season One, Episode Four – Blair and Serena

    Blair and Serena's photoshoot. They both wore matching long-sleeve dresses in vibrant colors. 

  3. 3. Season One, Episode 10 – Blair and Serena

    On their society debut, B and S transport us back in time with the vintage aesthetic of their gowns.

  4. 4. Season One, Episode Thirteen – Blair 

    B can literally put on any piece of clothing and it looks iconic.

  5. 5. Season One, Episode Fourteen – Jenny

    Little Jenny with her purple bag blew away New York City! 

  6. 6. Season Two, Episode One – Blair and Serena

    Serena and Blair took on the Hamptons with effortless class!

  7. 7. Season Two, Episode one/two – Blair and Serena 

    The White Party didn't stop Serena and Blair from allowing their opposing personalities to shine through their outfits. You can tell throughout that Serena is a lot less reserved than Blair. 

  8. 8. Season Two, Episode One – Chuck

    The boys’ outfits were amazing, including this all white suit that Chuck Bass wore. 

  9. 9. Season Two, Episode Ten - Blair

    Accessories were Blair’s best friend (after Serena, of course). 

  10. 10. Season Three, Episode Eleven - Serena

    During Thanksgiving dinner, S looked astonishing in her black jumpsuit. Fans went crazy looking for it in stores when the episode was originally released.

  11. 11. Season Four, Episode Two – Serena

    In Paris, S wore the perfect outfit for the City of Light: a gold sequin jacket with the blue capri pants.

  12. 12. Season Four, Episode Two – Blair

    Do we even have to say anything about Queen B’s dress? 

  13. 13. Season Four, Episode Eight – Serena

    Serena's dress was absolutely gorgeous and elegant with the lace.

  14. 14. Season Five, Episode Eight – Blair

    For Blair’s bridal shower, she wore a sequin Dior dress.

  15. 15. Season Five, Episode Nine – Serena

    Serena wore a gold, Diane Von Furstenberg dress for a party in honor of her grandmother, CeCe.

  16. 16. Season Six, Episode Five – Georgina

    Georgina Sparks wore a black sequin dress at the Debutant Ball. Her confidence is always an accessory to her outfits.

  17. 17. Season Six, Episode Ten – Blair 

    B’s wedding dress had her looking like Cinderella. The color, design, and silhouette was effortlessly graceful. Adding to all of beauty, she wore the finest jewelry. 

  18. 18. Season Six, Episode Ten – Serena 

    Serena wore a design by Georges Chakra. If you thought you could only marry in white, Blair and Serena proved you wrong!

What look from the television show did you like the most? There is so much high fashion on Gossip Girl that it's hard to choose!