Farewell Upper East Side, I Hardly Knew Ya…

Ok, I didn’t know you at all. Who am I kidding? This blog is called CHEAP wine and panty lines, not super expensive…champagne. Or whatever it is rich people drink. 

So, Gossip Girl just ended and my sister asked if we could do a fashion retrospective, and c’mon, obviously. The show might be total fluff, but what’s better than looking at and judging the stupidly expensive clothes they use to dress that fluff up. 

I already wrote the intro to this article here, and if I wait a second longer to post her contribution, my sister might actually murder me. She had a lot to say (haha) about her Gossip Girl fashion crush, prepster Blair, so…without further adieu, here it is! Enjoy! And while you’re reading this, I’ll start in on my very own retrospective for that uber babe ne’re do well, Serena. 

… … …

Ah, Gossip Girl. After six seasons of delightful braincations, it’s bittersweet to see you go. What began as a witty, simple indulgence has spiraled over the past six years into a bevy of some of the soapiest absurdities ever seen on prime time television. How we will miss your convoluted plots involving endless scheming, drug overdoses, embezzlement, unplanned pregnancy, royal weddings, incarcerated innocents, false identities, comas, and of course, a faked death.

In spite of the ridiculousness of most GG “plotlines,” one tried and true element of the show has kept us tuned in every year – The Fashion. Gossip Girl is basically fashion porn, with its frequently spectacular (and occasionally hideous) sartorial adventures.

My favorite has always been Blair Waldorf, the Audrey-obsessed preppy gamine with doe eyes and a perfect pair of lips.

Season One – The Ultimate Prep School Girl

In season one we meet Blair – and her headbands – for the first time. She shows us the perfect blend of prep and flair, always accompanied by a perfect hair accessory.




Love, love, love. (Lou – I’d totes wear that first outfit and wish my makeup face looked like that every day)

No clue what that crazy bow-tie thing is in the third shot, but it doesn’t matter because she pulls it off. Like those white tights (an accessory seen almost as often as her headbands); who wears white tights over the age of six without looking like a moron? Blair Waldorf, that’s who. She pulled almost everything off in season one, except this:


I disagree, internet collage-maker. I hate everything about this look. Except maybe the shoes, but it’s hard to focus on them in the face of that pink bouquet vomit bubble halter dress monstrosity. (Lou – yeah. Agreed. I could write a hate parade about bubble dresses with a special section devoted to pink bubble dresses.)

Season Two – Senior Year  

Blair is still in high school, but we’re supposed to believe she’s Becoming A Woman, so more grown-up outfits accompany her headbands and we start seeing her out of uniform more often.

Summering in the Hamptons, naturally.




Ps. Chuck Bass. That is all.

Season two also proffered one of my Favorite Dresses Ever (including A better view, on a model):



LOVE this dress. Want this dress. UGH. This Effing Dress! (Lou – Um, I can’t wait to write about how LAME this dress would be in Serena’s book because there is nowhere to display BOOBS! But it is a really pretty color.)

The Internets tell me it is: Blair Waldorf’s green backless Alexandra Avidal Thanksgiving dress from Gossip Girl 2.10 “The Magnificent Archibalds.” In case anyone wants to hunt it down and buy it for me. Or make me one, if you’re crazy impressive with a sewing machine.

Seasons Three and Four – Grown Ups?

This is what happens when you have a successful teen show and your teens enter “adulthood.” Or at least college. Their teen lives become more and more contrived as their forced into the “real world.” Lucky for us their clothes also grew up, and became more magnificent. This is exactly the cape I would want to be wearing if my smoking-jacket-clad billionaire boyfriend was trying to apologize to me with yet another bouquet of perfect peonies. And I would take any excuse to don that perfect pink confection of a dress. Society ball, night at the opera, grocery shopping…



(Lou – that cape does really, really weird things to her arms. And pea green is kinda gross. But in general I love the idea of capes.)

Ever wonder what to wear to the Musée d’Orsay when contriving your own Cinderella moment as you bid farewell to your suitor the Prince of Monaco? Look no further, these polka dots are just the ticket:

Double Identity

Not sure what season Blue Dress is from, but I love it and it deserves some commemorating. Clearly I am a sucker for backless dresses. S looks pretty great here, too.


Seasons Five and Six – The Denouement

And so we are at an end… Things have gone completely catawampus in the last couple seasons of GG, but the fashion still reigns supreme. B traded her headbands for hats, and the result was delightful. Note: In season five, for whatever reason, someone decided B’s hair had to look kind of awful all the time. The hats definitely helped.


On a non-fashion aside, I kinda liked B and Humphrey together. While Chuck was obviously B’s penguin, she and Lonely Boy still made sense. And back to B’s fashion, how much to I want those effing shoes???

We also have B’s wedding dress this season (because she’s what, 20 now? totally sensible age to wed) and in her (of course) Vera Wang she did not disappoint. Even though her hair is… sigh. Oh what’s that? She looks Distressed, you say? This is GG people. No such thing as a wedding without some Major Drama.



This look is perfection. I just want more reasons to wear Gowns. Or maybe just more gowns to wear anywhere I please.


With the final season, B brings it all back! Headbands! Hats! Polka dots! Gowns! Headbands with gowns! And there may even be another wedding dress in her future…





OMG is this B’s wedding dress??? Is she marrying Chuck and super grumpy about it??? It’s probably just a ruse… right? Only time and the CW will tell…


Ps. Lou and I now know the answer to this question, but in case you haven’t had a chance to watch the most ridiculous series finale of all time, we will avoid spoilers. xoxo

Thanks for all of the enviable ensembles, B. You and your dream wardrobe will be missed.

(Thanks sis! Looking at Blair’s preppy fashion wonderland got me all excited to write about naughty Serena’s T & A baring ensembles. …Also pending, a hilarious glimpse into the neon-loving lifestyle of gallery-owning babe extraordinaire, Paige. Until then… xoxo Lou)

One response to “Farewell Upper East Side, I Hardly Knew Ya…

  1. Pingback: XOXO, Gossip Girl « Real Living Beauty

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