Gossip Girl's Best Outfits

While in quarantine these past few weeks (and maybe a little before) I started re-watching Gossip Girl. It has been a great distraction from the rest of the insanity in the world and also given me so many great outfit ideas. The best reason to watch Gossip Girl is the outfits, no you cannot change my mind. Below I have done a round-up of my favorite outfits of the main 4 female characters, and I know this isn’t the usual kind of content that I do but desperate times am I right? I hope it helps to fuel the work from home outfit inspiration for everyone!

Serena Van der Woodsen (Blake Lively)

Serena Van der Woodsen has a very bohemian, Free People vibe kind of style. She is still dressed to the nines for most people, but on this show, she is one of the more casual dressers. She is one of the only women who will wear flats, maxi skirts, and crazy bright colors whereas most women in the show wear more neutral colors or metals. Serena is the freest spirted and her clothing reflects that. Her style is maybe the closest to mine in the show, and her style is also the cheapest to replicate! Her style does tend to be very girly but in a way that is more relatable than someone like Blair. It is the light, airy, fun kind of girly that most women have within them. Her free-flowing style partnered with her long, messy-in-the-perfect-way hair is the ultimate boho babe look. She has been inspiring ladies for years with her perfectly imperfect style, and I am no different.

Blair Waldorf (Leighton Meester)

When it comes to style, Blair Waldorf has my least favorite in the show. It is very preppy and very overdone in a way that makes her wardrobe feel the most like a costume. With Serena, there were actual outfits in their people could easily wear. The only place of the outfits Blair wears would fit in are on the Upper East Side. This works out well since that is her whole thing; Blair is the epitome of the Manhattan Elite social scene and her clothing truly shows that. I like her personality much more than Serena’s and find her one of the funniest charters on the show, her style just isn’t my favorite. I love her formal wear much more than her everyday wear, but I wanted this post to be a way for people to get inspiration from so I have refrained from posting any formal looks. My favorite outfits from her are the ones with the most insane print matching since this is as whimsical as her style gets. Blair is also the queen of accessorizing which I want to add more of into my wardrobe.


Jenny Humphrey ( Taylor Momsen)

Jenny Humphrey has my favorite outfits in this show. She embodies the punk rock, badass sense of style I have always loved. While I feel like my own style is somehow a mix of her and Serena’s, Jenny’s commitment to a dark and moody fashion sense is amazing. Her style changes the most in the show as she goes from the little preppy girl who wants to be Blair’s best friend in season 1, to a hardcore fashionista/designer by season 2. By season 3 when her character leaves the show, Jenny’s style is at its peak wonderful. Her dark lipstick is my favorite (loooooove me some dark lipstick) and her long bleached hair helps to contrast her moody style. When I first saw her style on the show, it showed me that even though I am tiny and blonde doesn’t mean that I have to be super girly 24-7. her jewelry is another favorite of mine, as well as all the bags she carries in the show. Purses are my favorite accessories and favorite fashion item, and her character has the best ones for sure. She mixes the glitz and glam in with the punk aesthetic and pulls it off flawlessly.


Georgina Sparks (Michelle Tractenburg)

Out of everyone, Georgina Sparks is the hardest charter to do my favorite styles from. As much as I do enjoy her minimalist (in terms of this show) style and dark color palette, she is only in the show a few episodes at a time and then we don’t hear from her for a while. These are my favorite looks from her even though they can be considered relatively simple. Again, her favorite outfits of mine are her formal looks, but she also has some very wearable pieces even if you are working from home and not stirring up trouble on the Upper East Side.

I hope this was a fun little blast from the past post that you can use to help draw inspiration from as you work from home or simply stay at home over the next few weeks. There is nothing more stressful than living through this time, so the more we can have fun and distract ourselves the better. And what better way is there to do that then to watch an incredibly dramatic show with great looks?

Madey