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See You Soon. XOXO, Gossip Girl Reboot

Hey there Upper East Siders. I hope you’re ready for the new Gossip Girl reboot because I sure am.


Recently, I’ve been rewatching the original and admiring all of the iconic outfits throughout all of the seasons. These looks will definitely be difficult to top in the reboot, but I hope they do it justice by honoring some of the staples from the show.

You know, all the legendary headbands, designer handbags, heels, and of course long fancy gala dresses that were worn throughout the six original seasons.

It is definitely safe to say that Blair Waldorf and Serena van der Woodsen had an influence in fashion while the show was being filmed. Everyone I knew who watched the show started wearing fancier outfits and headbands, in true 2007 fashion.

In honor of the Gossip Girl reboot, here are some of my favorite outfits from the original show.

Serena van der Woodsen

I'd say Serena’s taste in fashion was always my favorite throughout the show, and she always made a statement through her outfits.

Source: Pinterest

The first grey dress is stunning and intricately detailed. I love the wrap around the waist and the beading on the dress. I think making it a long dress by adding sheer lace to the bottom and the sleeves ties the dress together and makes it elegant.

Source: Pinterest

This next look was one of my favorites when I first watched, and still holds a special place in my heart.

The gold blazer with shoulder pads is such a power move. I like that it is paired with a brighter blue colored pant because it makes the look more fun and interesting. Her choice of handbag made a small remarkable statement without taking attention from the outfit itself.

Source: Pinterest

The third look is a champagne colored mini dress with a white square pattern paired with a grey blazer and cheetah print purse. I like the hat with this look, it gives me tourist-y vibes.

Source: Pinterest

The last look is Serena’s school uniform and I think we should take a minute to appreciate just how cool it is. It definitely is not a traditional school uniform and I love it.

The skirt and tie are my favorite, especially since most schools wouldn’t allow girls to wear ties as part of their uniform.

Blair Waldorf

When I think of Blair Waldorf, I immediately picture her wearing a headband or hair accessory accompanied with a new handbag.

Her style on the original show was preppy and chic, so I’m interested to see how the reboot keeps some of Blair’s signature spirit alive.

Source: Pinterest

This dress hasn’t left my mind since I first saw it on the show. The details on the sleeves are stunning and the dress itself is a beautiful burgundy.

She pairs it with a black clutch and has her hair pulled back which makes it look even more formal.

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This next look kind of makes me think of Cruella de Ville but make it chic. It’s classic Blair, a patterned peacoat over a black dress, tights, and heels.

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I think I would hate this look if anyone but Blair Waldorf was wearing it. But as long as Queen B is wearing it, it’s cute okay?

The gold headband is a small detail that ties the look together by bringing in some of the gold in the purse.

Speaking of the purse, I think this is the biggest bag I’ve seen anyone wear to class.

Source:: Pinterest

We saw Serena’s school uniform, but Blair adds some flavor to it by pairing it with red tights and a light-yellow pea coat. She wears a headband, of course, and a brown bag instead of a backpack.

Honestly, showing up to school without a backpack is kind of a power move.

Jenny Humphrey

Lil J started off sweet and innocent but by season two she was causing chaos and her style on the show changed drastically.

From the first episode of season one, we saw that Jenny loved fashion and would make her own clothes to try and fit in with the rest of the kids at her school. Fashion was an integral part in Jenny’s life and we can see the change in her personality through her style on the show.

Source: Pinterest

This first look represents the sweet and innocent Lil J we love. Her bubbly personality is shown through her brightly colored wardrobe and accessories.

She pairs a royal blue headband with a sage peacoat with a detailed collar, a red blouse and heels with polka dot socks, and finishes the look off with a purple handbag. Super cute and fun for young Jenny.

Source: Pinterest

This next look is definitely the opposite vibe of season one Jenny Humphrey. She replaced bright colors with neutrals and dark makeup, handbag for binder, and heals for a grunge style boot heel.

I actually love the dress she is wearing and the layered necklaces add a cool element to the look. Her style is totally different from most of the other characters in the show which is why Jenny always stands out and is able to draw attention to herself.

Source: Pinterest

I had to include one of Jenny’s dresses. While most of the characters on the show primarily wore long flowy gala dresses, Jenny went for a shorter and tighter silhouette, demonstrating that she was no longer the naive Lil J that everyone saw her as.

Jenny’s style plays an important role in the show because we see how what she has been through affects her, translating those emotions into her new style.

Chuck Bass, Nate Archibald, & Dan Humphrey

While the guys of Gossip Girl have their own unique style, most of it includes suits or jeans and a button up (if you’re Dan Humphrey).

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I’ll start off with Chuck Bass, who wore a suit 95% of the show.

I don’t have much to say other than the fact that he looks great and is a total pro at color matching and wearing ties that contrast his suit.

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Nate Archibald.

My personal favorite of the Gossip Girl guys. Like Chuck, he wears a suit, however, Nate either dressed like a businessman or a frat guy. I’m not sure which I loved more.

Both styles are great and give his character more range in the show to reveal his mysterious character through the help of his fashion choices.

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Lastly, we have Dan Humphrey.

In the original show, Dan was from Brooklyn which apparently meant being ‘poor’ (as Blair so kindly phrases it) and hanging around super rich kids.

His style reflects the “low-income” family budget he comes from, meaning that during the show he mostly wore slacks and a button up or jeans and a t-shirt.

His style got better as the show went on but, like Jenny, his style helped tell his story and reveal that he was “different” than everyone else he was surrounded by.

The White Party

Lastly, I couldn't end this without including the looks from one of my favorite episodes, "Summer Kind of Beautiful" where the characters go to the iconic White Party.

This episode had some memorable looks, like Blair's cocktail dress and headband combo, Chucks White suit with black piping and sunglasses hanging on the dress shirt, Serena with a gold headband and flowy floor-length dress, and finally Nate with a simple white tee and jeans.

I think if I could be in any Gossip Girl episode, it would be this one solely based on the fashion at this party.


Watching the original show and looking at all of the iconic fashion is not only making me want to take a trip to New York City, but is also getting me excited for the reboot.

Since the original costume designer, Eric Daman, will be returning for the reboot, I am confident the fashion will be just as iconic as in the original and will be inspired by some of the looks Blair and Serena wore through the streets of Manhattan.

See you next time Upper East Siders,


Gossip Girl


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