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Best Dressed: Gossip Girl Edition

Best Dressed: Gossip Girl Edition

We all know and love Gossip Girl, but have we ever taken the time to appreciate Gossip Girl fashion? Here are the best-dressed characters from all six seasons, as well as the ensembles that continue to inspire us to this day!

1. Blair And Serena In The Hamptons

First up on the run down of the best Gossip Girl fashion has to start with the gorgeous outfits that icons Blair and Serena wore when in the Hamptons in season two. Everything about these ensembles scream summer in the Hamptons; from the colorful and fun dresses to the perfectly coordinated accessories. We are obsessed with the summery bags and carefree vibe of the look, which strays away from their more typical NYC city girl outfits. The best part is that each of their outfits fits their characters so perfectly and gives us a refreshing new ensemble! 

2. Blair White Party Dress

Next up on Gossip Girl fashion is a classic, the dress that made all of our jaws drop when we saw Blair strut into the all white party. We are not sure exactly what it is about this ensemble that is so appealing, maybe it is just the fact that Blair pulled it off so beautifully. The white scalloped bandage dress complemented perfectly with her clutch and matching signature headband; we are totally obsessed with this entire outfit. Not only because Blair happened to be wearing this dress when she uttered her signature line  “Three words. Eight letters. Say it and I’m yours,” this only adds to the ensemble’s iconic status.


3. Blair School Uniform

Nothing beats signature looks when it comes to Gossip Girl fashion, and the characters’ school outfits are ones we can never forget about. This look in particular is one that will immediately pop in your head when someone mentions the name Blair Waldorf; clearly the Constance Billard School for Girls students had some pretty fashionable uniforms and we are all here for it. From the MET steps to the school halls, Blair was always serving looks filled with plaid, layering, and of course an adorable headband. 

4. THIS Serena Look

If Gossip Girl fashion could have a picture definition, this Serena outfit would be it. Nothing screams iconic more than a checkered patterned and glittery dress paired with an adorable fedora and an oversized blazer. Serena Van Der Woodson has proven to us time and time again that she can make anything work, that includes mixing different patterns and materials! What seems to always be a factor in our favorite Gossip Girl outfits is the random mix of clothing items that just end up working perfectly, even if we never would have thought to pair them together. 

5. This Masterpiece Of A Dress

Sometimes Gossip Girl fashion leaves us in such awe that we no longer know how to put into words how beautiful an ensemble is, this dress is an example of one of those moments. This monumental piece of clothing that Serena opted for to wear to an evening at the New York City Ballet is one of the most daring and gorgeous pieces that she wore on the show. The bold grey color complemented Serena’s bright locks perfectly, as well as the head to toe silhouettes of lace floral and sheer material; basically everything about this dress is absolutely to die for.


6. Serena’s NYC Girl Looks

Like we said before, nothing beats a classic Gossip Girl fashion look, especially an iconic Serena ensemble as she struts the streets of the Upper East Side. We constantly take inspo from Serena’s winter and fall fits; the way that she can throw on a chic blazer and a fashionable pair of tights to complete any outfit really shows that Serena is a fashion expert. Nothing beats this outfit in particular, the sheer plaid tights, knee high boots and cashmere gloves all create an iconic Fall NYC outfit that we are dying to copy.

7. Innocent Jenny’s Yellow Coat

Before Jenny went all goth on us, she had her moments with outfits that deserve to be on the best Gossip Girl fashion list. Although we can’t hate on Jenny simply for changing her fashion style, we have to take a moment to give credit to her preppy moments in season one. We always love to see the characters taking on cold NYC weather with fashionable layering and when Jenny pulled through with this fabulous yellow trench coat over her school uniform, we have to admit that we were impressed. Accessorizing with a bright blue headband and gorgeous pink purse added more life and color to her ensemble that we love! 

8. This Iconic Duo Outfit

It is a known fact that Gossip Girl fashion would not exist without Serena and Blair, which is why we love when they pull through with iconic duo outfits. Everybody has seen this one in particular because it serves as a perfect example of adorable matching outfits with your best friend! An Eleanor Waldorf original, these open back sheaths paired with metallic pumps create the most gorgeous outfits that we all are dying to try with our best friends. Plus, the tiny belts, adorable head scarf and bold red lipstick all complete the look in an effortless way!


9. This Gorgeous Gown

When Blair went to meet with Chuck in Paris, she made sure to look absolutely stunning when doing so. This absolutely, jaw-droppingly, gorgeous Oscar de la Renta gown is pretty much unbeatable. Everything from the matching shoes to the clutch that complements the gown almost too perfectly, not to mention her absolutely beautiful and elegant jewelry that we simply can not stop staring at. As if the bold red color of the dress matching Blair’s lipstick shade was not enough, of course the design of the gown itself can not be matched.

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10. Chuck’s Coordination 

We can not possibly make a list of the best Gossip Girl fashion without giving some credit to the men of the show, especially the famous Chuck Bass. Whenever he is pulling some random and oftentimes catastrophic scheme, Chuck always makes sure that he does so in style. It is no wonder that Chuck is always wearing very coordinated and stylish outfits, considering he is in love with Queen B and Queen of fashion, Blair Waldorf. We love the outfit pictured below in particular not only because of its impeccable coordination but also because it includes a brighter and more fun color scheme than we usually see Chuck wearing. It is always heartwarming to see Chuck smiling, and a lighter color scheme in his ensemble really adds to that ambience. 


11. Blair’s Green Moment 

This next Gossip Girl fashion moment is another one that we love because it showed a more unique twist of Blair’s usual style. As the seasons went on, Blair’s style seemed to mature throughout the years from plaid skirts and busy headbands to more chic yet still fun ensembles. This green dress serves as the perfect example as it is a gorgeously fresh color and pattern yet Blair still managed to make it look more sophisticated with a simple headband and minimal accessories, they really grow up so fast!

12. Gold Glittery Gown

The final look in our Gossip Girl fashion run down is another one of Serena’s many iconic moments. Nothing complements Serena’s gorgeous locks more than a glittery golden dress and matching bulky necklace and chunky bracelets that have her looking like she is literally dripping in gold. Plus, the change from her normally wavy or straight locks to voluminous curls really added to the whole look.

We hope you’ve enjoyed our run down of the best Gossip Girl fashion throughout the six seasons!