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23 Times Chuck & Blair Were the Best-Dressed Couple EVER


Prepare to feel really old—it’s been 10 years since Gossip Girl premiered, coming into our lives and forever making them better. The show that gave us Blair Waldorf and Chuck Bass also provided some of the greatest style moments in TV history, many of which were thanks to the OTP. Though it was hard to narrow down, we’ve picked 23 of our favorite ensembles from the duo to prove Chuck and Blair were by far the best-dressed couple EVER.

1. Masters of the uniform

Nobody quite does uniforms like C and B. They got it right time and time again in their Constance and St. Jude’s duds, which was the first indicator that their style would be on point for years to come.

2. In the trenches

Before these two were even a legit couple, they were taking wardrobe tips from each other.

3. Matching is key

Let us make one thing clear: Chuck and Blair were always at their best when wearing matching outfits. These green ensembles from the show’s Season 2 Hamptons tenure set the precedent for what would become GG fashion law.

4. Cotillion

Keeping their as-yet-undefined relationship under wraps at Cotillion, we were elated seeing Chuck and Blair step out at a formal affair together for the first time. It’s really B’s bow-shouldered silver gown that shines here, with Chuck’s attire selflessly playing second fiddle to amp up their overall look.

5. White party

Who could forget the White Party? Certainly not us! These outfits may be etched in our memories because of the all-important three words, eight letters conversation, but that doesn’t make them any less scene-stealing on their own.

6. Always bring peonies

Chuck just told Blair he loves her! Chuck just told Blair he loves her! Okay, we’re getting a bit distracted. But aren’t these looks just as flawless as this moment?

7. Summer lovin’

New coupledom looked swell on Chuck and Blair, are we right? Starting out a love-filled Season 3 on a high note, this moment cemented that the duo’s style is even better together.

8. Power couple

We have basically the same feelings about this as we do about #7. Probably because it’s from the same episode. We just couldn’t choose.

9. Polo match

On any other people, these colors might look completely ridiculous. But not on fashion risk-takers like Bass and Waldorf. Confession: This is indeed from the same episode as #7 and #8. What can we say? They were three for three.

10. College, here she comes

Keep in mind we would never wear pumps on our first day—or really any day—of college, as Blair did. You can take the Queen B out of the UES, but you can’t take the UES out of the Queen B. Chuck seeing her off for her big NYU adventure was just the cherry on top of this look.

11. Speakeasy costumed

Costume parties always lent a nice change of pace to the Gossip Girl fashion norms. Season 3’s prohibition-style soiree allowed Chuck and Blair to do the two things they loved most: scheme and look superb doing it.

12. Flashback dreaming

Old Hollywood dream sequences make for outstanding style moments, don’t you think? Dressed to the nines, these two come out on top… even if Vanessa did best Blair in her All About Eve-inspired nightmare.

13. Wintry mix

The coldest months aren’t upon us yet, but winter is coming. That’s why we’ll be taking inspiration from C and B’s bundled up chic layering.

14. Wedding guests

We’ve seen a fair share of UES weddings, but an outdoorsy fall theme allowed for palettes that we weren’t used to seeing on this bunch. Switching up their ordinarily proper ensembles for these more relaxed silhouettes was a welcome change.

15. Cordially invited

At this point, we’ve almost run out of ways to describe their endlessly spot on style. This is just another great example of Blair and Chuck’s fashion expertise. Shall we move on?

16. Business not-so-casual

We loved seeing Blair in a suit after years of watching Chuck slay in the menswear department. This outfit gently pointed to Blair’s inevitable success as a businesswoman, as she reached her career goals so she could be with Chuck once and for all.

17. Monkey business

That cute little mutt that stole Chuck’s heart is a mere distraction. Because bumping into your former beau at the duck pond never looked so good.

18. Adorbs, even apart

Don’t be fooled by the hand holding. Chuck and Blair were not together in this episode. But aren’t they cute together?

19. On a mission

The mixing of prints and colors here should throw us off. But B and C found a way to stand out among a sea of lame dressers, which was kind of their superpower.

20. Party crashers

This episode had a lot of ups and downs, and we’re not just talking about the bar mitzvah chair—all the puns intended—ritual thing. These clothes looked almost as great on as they did getting ripped off in the steamy scene that followed.

21. Meet in the middle

Be still our beating hearts! This was pure magic, from the setting to the wardrobe to the pair’s first chilling encounter after Chuck’s near-death experience. But what we adore about these outfits is the juxtaposition of Blair’s stunning gown and the commoner’s clothing Chuck is wearing. It’s something we never thought we’d see on GG, but we’re oh-so-glad we did.

22. Building their Empire

This has got to be our favorite on the list. The coordinating colors and pure joy here set these ensembles apart from all others, in our opinions.

23. I do times two

Stop the presses. Introducing Mr. and Mrs. Bass in the stunning outfits they wore to—FINALLY—marry each other at Bethesda Fountain. What a perfect way to end the series! Excuse us while we pin this to our “bride-to-be with no engagement ring” Pinterest board.

Which of Chuck and Blair’s looks is your favorite, collegiettes?

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