5 Day Style Challenge: How To Dress Like Gossip Girl Blair Waldorf

I know most of you have watched, or at least heard of Gossip Girl. The mid 2000’s drama about socialites, fashion, high school and well GOSSIP! Blair Waldorf was always my favorite when it came to fashion, her signature headband collection definitely had more volumes than the book series for sure! So if you love Blair, or are interested in creating looks that are Blair inspired I’ve got you covered! – Just don’t tell her how affordable these looks are or you won’t be sitting on the steps of the MET for lunch.

Tweed Need The Gossip

Blair’s style is classic. Lots of dresses, heels and headbands, so to start off this style challenge I chose a tweed. Tweed is a heavier, chic textured fabric that usually appears in the fall and winter, but in lighter tones, can be worn in more seasons. Here, I have this adorable mini dress with embellished neck bow which has a flattering, tailored fit. Blair usually wears stockings but as I live in Texas that won’t be happening – it’s just too darn hot! So please keep that in mind with all of my inspired looks, they are geared for Houston weather, not NYC. The plus to this is you can see how easy it is to adapt her style to any season or location.

Polka Dots & Promises

Just like Serena and Blair promise to always be there for each other, so does Blair’s love for tops with tie accents. I decided to adapt this trend with an organza polka dot top and black mini skirt. To finish this look off, of course I had to add in a headband. This pearl one is super comfortable and adds a subtle touch of classic glam to finish off the look.

Eyelet You In On A Secret

So many secrets to cram in one show, sometimes it’s hard to keep track of how many are even in one episode – gotta love the drama. One of my favorite Blair looks was this beautiful 60’s silhouette eyelet dress. I chose a different 60’s silhouette, but kept with the eyelet theme and crisp white. With black accessories and a pearl embellished headband this look is all Blair and ready for the All White Party.

Winter Waldorf-land

I’m pretty sure Blair had a coat to match every headband in the Big Apple, but here in Texas, well, we don’t need that many so for a Blair-worthy winter look, it’s all about the layering. Here I have on a lightweight trench in an adorable polka-dot print with a turtleneck top, light woven sweater, mini skirt, and over-the-knee boots. This look ties in elements of Blair’s’ classic ensembles but with sensible pieces for a southern climate.

Classic Blair School Uniform

During this show’s first few seasons the characters were still in high school which meant uniforms. Though the dress code obviously was not very strict and most took creative freedom to put together their looks, Blair’s were still relatively uniform but with added accents to make her stand out. This look is actually all Amazon and was totally my favorite to put together – though to be honest, I felt a bit like I was in a costume. I’ll admit this look is not the most practical, but it was a lot of fun to put together and wear. Plus if you are looking for a Blair Waldorf costume, this is totally the way to go!

Gathering up all of these Blair looks was seriously so much fun! I love and excuse to watch Gossip Girl so the homework for this style challenge was a blast, and honestly I pull inspo from Blair pretty often. I have pulled a few other looks that have her “flavor” and have added them here as well! I hope this gives you lots of ideas on creating looks inspired by this Gossip Girl socialite. Until next time – xoxo GG