11 Best Diamond Moments From the Original “Gossip Girl”

With the Gossip Girl reboot right around the corner (guys, it looks SO good), we thought we’d take a trip down memory lane with a look back at the best diamond moments from the original Gossip Girl series.

The fashion across the board on the OG Gossip Girl was truly incredible, but of course, the style stand outs had to be Serena and Blair, with an honorable mention to Chuck for his dapper suits.

Eric Daman lead the costume department on the original show, which included styling by Jennifer Michalski-Bray, so clearly the team knew what they were doing when dressing the cast. From ballgowns to zshushed up school uniforms, GG’s leading ladies quickly became fashion icons for those of us who watched the show religiously and, let’s be honest, still rewatch today.

The show catapulted all its stars to instant fame and teen idol-dom. We loved the ridiculously dramatic plotlines (Bart Bass’s fake death anyone?), the incestuous relationships between the main characters, the fact that Dan was supposed to be broke but lived in a giant loft in one of Brooklyn’s most desirable neighborhood, not to mention the reveal that Dan is Gossip Girl, which was probably the least believable plot line in the entire series.

But the most believable part of the series by far, was Serena and Blair’s impeccable wardrobe. Blair’s preppy chic style a la Audrey Hepburn, complete with her signature headbands, holds up today and Serena’s boho model-off-duty vibe still lives in my mind rent-free. And it goes without saying that both wore some seriously incredible jewels.

Ahead our favorite dazzling diamonds from the original Gossip Girl series, as worn by style queens Serena Van Der Woodsen and Blair Waldorf.

1. Blair’s Harry Winston Engagement Ring

Let’s start with the obvious: Blair’s gorgeous engagement ring from Harry Winston. We’re calling this one her official ring, as it came from Chuck (and not that evil Prince Louis). The cushion cut ring flanked by baguette diamonds on each side is so very Blair Waldorf.

2. Blair’s Royal Wedding Jewels

Runaway bride Blair left Prince Louis at the reception of her wedding along with some serious diamonds on her head and neck courtesy of the tiara and necklace. Not to mention the yellow diamond engagement ring from the evil Prince… more on that in a bit.

3. Blair’s Fiery Red Dress & Matching Necklace From Harry Winston

We all know and love this outfit from the scene where Blair finds a disheveled Chuck in Paris and gets him to come home to NYC. She may not love him anymore but we sure do love that ruby and diamond necklace from Harry Winston!

4. Serena’s Statement Drop Earrings

Serena Van Der Woodsen *loved* a statement earring. And a statement necklace. And a chunky bracelet. Serena’s wardrobe was a bit all over the place (can you tell we’re Team Blair when it comes to fashion) but one thing is for sure: She knew how to dress up for a black tie event.

5. Blair’s Central Park Wedding

Chuck and Blair’s epic love story culminated at the Bethesda Fountain in Central Park, where our favorite couple tied the knot so Blair couldn’t testify against Chuck in court (if you haven’t watched, it’s a long story). Blair’s blue Elie Saab dress pair perfectly with her turquoise and diamond earrings, topped off, of course, with a diamond headband.

6. Serena’s ‘20s-Inspired Earrings

At a roaring ‘20s themed party, Serena opted for a little sparkly dress, her hair pulled off to the side, and art-deco-inspired dangling diamond earrings.

7. Blair’s Yellow Prom Diamonds

Second only to her Elie Saab wedding dress, Blair’s black and gold prom dress was perfectly accessorized with a yellow and white diamond necklace with a cocktail ring and sparkling headband to match.

8. Blair’s Debutante Ball Diamonds

Blair’s perfect coming out may have been ruined by frenemy Serena, but her look stayed flawless despite the drama. Normally, with a statement bow like Blair’s we’d shy away from pairing it with a statement diamond necklace, but she totally pulls off the look, with matching diamond earrings of course.

9. Serena’s Delicate Drop Earrings

What does a casual day for it-girl Serena Van Der Woodsen look like? Oh, just some dainty diamond drop earrings paired with a fabulous Burberry coat!

10. Blair’s Audrey Hepburn Diamonds & Serena’s Marilyn Monroe Diamonds

GG fans will remember this scene from one of Blair’s fantastical dream sequences, a play on Blair’s obsession with Audrey Hepburn and her persistent fear that Marilyn Monroe-esque Serena will upstage her at every turn. But when they both look this good decked out in diamonds, we’ll have to call it a tie.

11. Blair’s Yellow Diamond Engagement Ring

While we’d all like to forget Blair’s stint with evil Prince Louis, we can’t so easily brush off the giant yellow diamond engagement ring he gave her. It’s just that stunning.

We can’t wait to see all of the new looks from the Gossip Girl reboot when the show premieres July 8th on HBO Max!