NYC Halloween: Blair Waldorf

White Shirt || Skirt || Ballet Flats || Handbag || Headband || Earrings || Watch || Bracelet || Optional: Navy Socks

Hey Upper East Siders! It would have been such a missed opportunity if I shared my NYC inspired Halloween costumes and didn’t include the legendary Blair Waldorf. The queen of the Upper East Side ruled Constance Billard with an iron fist. Each day of her reign started with breakfast al fresco on the MET steps with her most loyal subjects. If dressing like Blair is speaking to you for Halloween is speaking to you, here’s what you should have. Don’t forget to shop your closet!

Must Have: White Button-Down Shirt

Keeping up with the prep school wardrobe, a crisp white shirt fits the bill. While a simple collared shirt would work, I loved the eyelet detail on this blouse from Old Navy. It seems like the perfect Blair Waldorf twist on a classic piece.

Must Have: Navy Wool Mini Skirt

I’ve had this skirt in my closet for years. Deep down, I always thought of this as my Blair Waldorf skirt. It took a while, but it finally lived up to the name. This simple wool skirt, from LOFT, is a more youthful take on a standard pencil skirt.

Must Have: Navy or Black Ballet Flats

I so often gravitate towards a simple pair of heels, I forget how good ballet flats are. I’m not sure what the dress code was at Constance Billard, but I wouldn’t be surprised if a classic Chanel flat was standard issue.

Must Have: Bold Headband

Of all the pieces in a Blair Waldorf ensemble, this is by far the most important. If you were an avid Gossip Girl watcher, you may have fallen in love with each and every headband she put on. This bright red headband from J. Crew just seems like the perfect one for the job.

Strongly Encouraged: Classic Handbag

Even though Blair was just in high school, she had great taste in handbags. I feel like she would be a fan of the whole Neely and Chloe collection. They are lady-like inspired silhouettes for a modern world.

Optional: Knee-High Socks

Some of the best Blair Waldorf recreations I’ve seen includes one more little feature. To cap off the prep school, a pair of simple navy or black socks go a long way. Speaking as a former prep school teacher, this is practically part of the uniform. That’s especially true on colder days when it’s a mild attempt to keep your legs warm.

With a Gossip Girl reboot on the horizon, your favorite show from the 2010s just became relevant again. In a world that’s always changing, it feels good to dress up like Blair Waldorf, years later.

Love from NYC,
Katie

Thanks for stopping by! As always, if you are more interested in travel than style, be sure to visit my exclusive travel page, here.