Once upon a time Blair Waldorf ruled the Upper East Side with her elegant and fashionable style. And she may still be ruling this side of New York, but we will find out soon-ish.

It was announced recently that Gossip Girl will be making a comeback, but with different characters. It will be interesting to see how they will work this out, and if they will mention or include in the storyline anyone of the original crew. In the middle of the news, I got to wonder (yet again) what would Blair be wearing in 2019. She has always loved timeless pieces, and was super elegant and preppy without being boring.

One of the things that made her the most iconic character from GG was her love for headbands. They were her crown during school years and, as she grew older, they stopped being an everyday item but still popped here and there. I believe Blair would be an advocate for the puffy headband trend, and would have multiples for every occasion in her life.

But this is not a post with 100 headbands Blair might have in her closet. This is a selection of 5 possible key pieces for Miss Waldorf in 2019. And, because not everybody can spend that much money on clothes, there is also a more affordable option for each piece.

• The ‘when in doubt’ dress

• The Statement Coat

• The Cinderella Pump

• The Not-so-Basic Everyday Bag

• The Tiara