Blair’s wedding doesn’t just mark the end (?) of Chuck and Blair – it also means that, at long last, our favorite Upper East Siders have made it to their 100th episode. While we might have missed Gossip Girl Day, we still want to celebrate five years of break-ups, backstabbing, smirky voice-overs … and, of course, some spectacular fashion.

Here are some of our favorite Gossip Girl fashion moments:


%image_alt%Ep. 1×01: Pilot

No matter what she’s worn in the past five years, this oufit will always be quintessential S to me (well, this and Ann’s school uniform photo). It might be the only time Serena has ever dressed appropriately for the occasion, and she looks so effortlessly chic. Her neckerchief was a great touch, she hasn’t yet forgotten how to brush her hair, and that leather pea coat is why cows were invented. I miss this Serena.
Amanda Smith


%image_alt%Ep. 1×03: Poison Ivy

Serena’s outfit from Poison Ivy amazed me. This was before everybody and their cat was wearing over-the-knee boots, and I was obsessed with them. I looked them up online and discovered they were actually affordable (from Chinese Laundry) and promptly bought myself 2 pairs. Sadly, I don’t have Serena’s legs, but I still enjoy strutting around in them. I may have occasionally work a loosened necktie like she did in this look.
– Ann Foster


This outfit is one of my favourites because Blair rocks vintage. You can take the girl out of the black and white Audrey Hepburn dreamscape, but you can’t take the sparkly beret and excess of hot rollers away from the girl – and the way yellow and navy is brought together in both dress and accessories is wonderful.

Bella Hall

%image_alt%Ep. 1×04: Bad News Blair

This was my favorite photo since I first saw it during season 1! I’m absolutely in love with these identical dresses that swoop down to their lower backs. This is a perfect best friends photo!
Carla Borderies


%image_alt%Ep. 1×09: Blair Waldorf Must Pie!

I luuurved the season 1 Thanksgiving episode, Blair Waldorf Must Pie. Not only because flashback S was wearing booties from Payless (not pictured) but because Blair introduced the world to the delights of patterned fishnet tights. Previously only worn in Victoria’s Secret catalogues, Blair’s UES teen queen brought this super-flattering, incredibly girlie look to the masses. These tights with bow patterns typify Blair’s s1 style. I blame this look on my current stockpile of fishnets. Plus, I may own a dress like this. And a lot of hairbands.
– Ann Foster


%image_alt%Ep. 1×11: Roman Holiday

Of course Blair would own a skating outfit. Of course it would be adorable. Of course the pom-poms on her skates would match her turtleneck. And of course Blair would find a way to make a turtleneck look cute.
Amanda Smith


%image_alt%Ep. 1×12: School Lies

Who else can mix and match patterns like that? Bold patterned scarf with a plaid trench? Unless you can say, “I’m Chuck Bass”, then you should avoid this master class in patterns. It’s not for amateurs. Then again, is Chuck Bass an amateur at anything? 
Lesley-Anne Steeleworthy


%image_alt%Ep. 1×15: Desperately Seeking Serena 

My choices are some old Chuck Bass and Blair. Not because I’m shipping on them or any of that junk. No, I just miss the colour. And the patterns. And the accessories. The two of them were mothereffing champs at mixing colours and patterns. And they accessorized like nobody’s business. It accentuated the scheming and the meanness and made it look awesome. And Blair didn’t have those dead eyes – maybe headbands are her life force.
Lesley-Anne Steeleworthy


%image_alt%Ep. 1×16: All About My Brother

Blair in uniform never fails to make me smile. And I love how she used to wear red ALL THE TIME.
Carla Borderies


%image_alt%Ep. 4×08: Juliet Doesn’t Live Here Anymore

Chuck may have gone a wee bit off the rails when he donned Blair’s robe, but he did it stylishly. Yummy texture? Check. Splendid detailing on the cuffs? Check. Continuing his commitment to purple? CHECK!
– Jen Luby


%image_alt%Ep. 4×01: Belles du Jour

Okay, so these aren’t a great fashion moment, but it’s definitely one of the most distinctive fashion moments in the last couple years. The Pants That Ate Paris have accomplished the impossible: making Blake Lively look pear-shaped. These pants prepared us, mentally and emotionally, for the utter insanity of seasons four and five. And, I’d like to think, they brought us together as a community – as tragedies often do.
Amanda Smith


Congratulations on 100 stylish episodes, Gossip Girl. For better or worse, you know we love you.

The You Know You Love Fashion Staff


Those are some of our top picks – what are yours? Let us know over on our Facebook page!