Fashion

A Back To School Guide: Gossip Girl Outfits

Under the spotlight today, fashion and school, or rather fashion IN school. No matter what year you are in, fashion is a big part of school life. It allows us to express our personality, it affects our mood and confidence, but it also plays a huge role on how other people perceive us. And, like Will Rogers said: “You never get a second chance to make a first impression.” So, here’s a back to school guide to help you find the perfect outfit for this season to make a powerful first impression. 

We will be taking a look at one, if not THE best TV show on the matter, Gossip Girl. So, if you still haven’t figured out what to wear this year, don’t worry, because whether you’re more of a Jenny Humphrey than a Blair Waldorf, I’m sure you will find something that suits your style! (oh and guys too!)

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Disclaimer: In this article, I will focus on the original Gossip Girl 2007 show, as I have not seen the reboot and do not intend to do so. 

Blair Waldorf

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The Upper East Side’s Queen B

Whether in Constance Billard St-Jude, NYU, Columbia or anywhere else actually, Blair’s outfits were always chic, preppy and polished. She never really stuck to the actual dress code in her high school, but did any of them really do? 

In her school looks, we can find a few staples that you can implement in your back-to-school outfits, such as: 

  • Skirts (pleated, pencil, …)
  • Shirts and Blouses (opt for a classic white or experiment with colours and prints!)
  • Tights (you can pass on them in the warmer seasons)
  • Some form of neck tie
  • Pumps or ballet flats
  • Headbands, they are a must in her wardrobe!
 
Here is a back-to-school outfit inspired by Blair Waldorf, that you can try. Feel free to switch things up with your own colour preferences and such! 
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Serena Van Der Woodsen

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Manhattan’s It Girl

S (nickname given to her by Gossip Girl) was the dream girl of New York. She was tall, blonde, rich, fun, how could anyone dislike her?…
Even if (spoiler alert) she ended up not going to Brown after her high school graduation, we still saw some of her school outfits in the first seasons. 

Serena’s style could be described as boho-chic, and unlike her best-friend B, she had a love for skinny jeans (although we can see her wearing skirts and dress very often! Most of the time, in fact.). 

For this Serena VDW back-to-school inspired look, I did opt for jeans and boots. One of her famous and favourite combo!

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Jenny Humphrey

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Little J

Once a Waldorf wannabe, Jenny Humphrey became the total rebel of the group. She found her own style, and we are all glad she did (at least I am) because she had some of the most ICONIC outfits. She was a great seamstress and fashion designer. So let’s try to come up with a good back-to-school outfit inspired by her (even tho she mostly skipped her classes)

Her style is kind of a chic punk-rock edgy mix, some might even call it goth-chic. She wore a lot of black, obviously, fishnets and tights, high heels, leather, patterns like plaid or tartan, studs, etc. 

Therefore, here is a back to school outfit inspired by Jenny Humphrey for all my strong-headed go-getters. And don’t forget to complete it with a bold lipstick, or change it up (like all black ankle boots and a nice red handbag). 

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Vanessa Abrams

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Documentary girl 

Vanessa was quite a controversial character in the show, some people liked her, others found her extremely annoying. However, it was not only her character that was controversial, but her style as well. 

I would describe Vanessa’s style as “eclectic-bohemian”, it wasn’t much of a fan favourite, still it was fun and bright. She liked to mix and match a lot of different patterns, textures, and colours. Also, we found a lot of layering, fringes, jeans (not just the garment, but the material) and various jewellery in her outfits. 

For the back-to-school outfit inspired by Vanessa Abrams, I decided to go with a bright-coloured dress and wedges, complemented by plenty accessories. Try it on! 

 

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Chuck Bass

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Alias Henry Prince 

Before getting the biggest glow up in the history of the show, Charles’s early days style was relatively more experimental, in a way. He used to wear more bright colours and flashy patterns, whereas after high school, it was fairly toned down. Nevertheless, he always remained classy and put-together. What a powerful couple did B and him make! 

One thing that was absolutely unforgettable for his school looks was his scarf! It was his signature look, and nobody could criticize him for it without consequences. 

Since the boys were the only ones to somewhat follow the dress code, here is a back-to-school outfit inspired by Chuck Bass, aka the richest kid of the Upper East Side. (PS: the whiskey bottle is obviously not necessary, unless you really are Chuck Bass 😉 ) 

 

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Nate Archibald

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The Knight in shining armor

Nathaniel was truly the preppy nice guy of the show. He was always there to save someone who needed help, and overall really was a great friend (when he wasn’t busy having a new girlfriend each week).

Once again, his style was totally preppy and classic, except when he was in a more relaxed sport mode. His style is mostly made out of neutral colours and classic cuts, making him really easy to style. And his outfits can look good on anyone!

So here is the back-to-school outfit inspired by Nate Archibald, that is a bit different from  his school uniform. And lose the coat if it’s too hot!  

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Dan Humphrey

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Lonely Boy

The writer of the group, Daniel Humphrey, brother of Jenny Humphrey, was the “simple guy”. Or so he appears to be…

His style was just as simple, he didn’t put too much thought into styling or accessorizing his outfits, whether it was in or outside of school. His whole character made him a bit more relatable to the average person. That also makes his back-to-school outfit more approachable for just another simple guy! 

Therefore, here is a back-to-school outfit inspired by Dan Humphrey that’s sure to please everyone. 

 

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So there you have it! Easy Gossip Girl inspired outfits for this back-to-school season that will hopefully help you stop saying, “Ugh, I don’t know what to wear!”. 
We went through the main characters of the show, men and women, and you now have all the basics to start dressing like the Upper East Side’s Elite. And don’t forget to add your personal touch to the outfits!

If you have any other style guide requests or want to read something in particular on the blog, leave a comment or contact me.

NDA: All of the images in this post are either embedded from Getty Images (all credit goes to them and the photograph) or created by me using Canva or other platforms. My images might be subject to copyright. 
If you want to repost this article or its images anywhere, ask for permission beforehand. Note that it will not always be granted.
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