25 Amazing Fashion Moments On “Gossip Girl”

Fashion was just one of the many reasons why “Gossip Girl” was such an incredible show. Check out some of the best clothes to ever appear on the show, pick up the complete sixth and final season of “Gossip Girl” on DVD or download it on February 12th and click here for a chance to win a designer outfit worn by the esteemed Blair Waldorf.

1. Blake Lively And Leighton Meester In “Hi Society” (S1:E10)

Eric Leibowitz/The CW

Just a couple of girls talking about the boys in their classes on the way to school. You know — something we all see every day.

2. Margaret Colin And Leighton Meester In “Roman Holiday” (S1:E11)

Eric Liebowitz/ The CW

Walks in the park with Mom are always so miserable!

3. Leighton Meester In “School Lies” (S1:E12)

Eric Liebowitz /The CW

Wait, you’re saying you’ve never did your math homework dressed in something like this?

4. Ed Westwick In “Summer, Kind Of Wonderful” (S2:E1)


Gotta go heavy on the white until Labor Day!

5. Leighton Meester In “New Haven Can Wait” (S2:E6)

Giovanni Rufino / The CW

Blair was always a master at pairing patterns together.

6. Leighton Meester In “Valley Girls” (S2:E24)

Giovanni Rufino/The CW

Of course this is what Blair Waldorf would wear to prom.

7. Leighton Meester And Ed Westwick In “Reversals Of Fortune” (S3:E1)

Giovanni Rufino / The CW

No one could ever accuse Chuck or Blair of not taking weekends seriously.

8. Ed Westwick And Leighton Meester In “Reversals Of Fortune” (S3:E1)

Giovanni Rufino / The CW

Would you believe this is what kids wear to discuss the terms of their “open relationship”?

9. Blake Lively In “Dan de Fleurette” (S3:E4)

Giovanni Rufino / The CW

You’d have to be out of your mind to let someone other than Serena Van Der Woodsen deal with your public relations (especially when you consider how gracefully she manages her own).

10. Ed Westwick And Leighton Meester In “How To Succeed In Bassness” (S3:E7)

Giovanni Rufino / The CW

You’re wrong if you think you can wear anything but flapper clothes to your club’s opening.

11. Blake Lively And Aaron Tveit In “Treasure Of Serena Madre” (S3:E11)

Giovanni Rufino / The CW

“Mom you know grapefruit juice is not a substitute for OJ.”

12. Chace Crawford In “The Unblariable Lightness Of Being” (S3:E18)

Giovanni Rufino / The CW

When you’re trying to make your best friend — the billionaire hotelier heir — feel better about himself, it’s important you look worthy of the task at hand.

13. Leighton Meester And Blake Lively In “Belles de Jour” (S4:E1)

Giovanni Rufino/The CW


14. Hugo Becker And Leighton Meester In “Belles de Jour” (S4:E1)

Giovanni Rufino/The CW

If only Blair’s future with Prince Louis was that starry.

15. Blake Lively In “The Undergraduates” (S4:E3)


Fashion’s Night Out is never to be taken lightly.

16. Ed Westwick In “The Undergraduates” (S4:E3)



17. Blake Lively And Leighton Meester In “Easy J” (S4:E6)


Friends stick together, EVEN IF one of them is dressed better than the other.

18. Blake Lively In “Easy J” (S4:E6)


I’m sorry, is there another way a student is supposed to seduce their college professor that doesn’t involve cutouts?

19. Chase Crawford In “War At The Roses” (S4:E7)


And this is what you wear when you are suspicious that one of your friends is schtupping your maybe-girlfriend’s cousin, the college professor.

20. Leighton Meester In “It-Girl Happened One Night” (S4:E15)

Giovanni Rufino/ The CW

This is outfit a girl wears when she’s in businesswoman mode and is about to ask her socialite best friend to let a reporter follow her around for a night of luxury and glamor!

21. Chace Crawford In “Yes Than Zero” (S5:E1)


This is a great example of what it looks like when a rich kid from New York tries to enjoy the relaxing vibes of California.

22. Blake Lively And Leighton Meester In “All The Pretty Sources” (S5:E8)


If you’re a pregnant and engaged college drop-out, New York is the best place for you to have your engagement party.

23. Michelle Trachtenberg And Penn Badgley In “Monstrous Ball” (S6:E5)

Giovanni Rufino/The CW

It’s always important to look dashing when chatting with the girl who had a baby and tricked you into thinking he was your son.

24. Leighton Meester And Ed Westwick In “New York, I Love You XOXO” (S6:E10)

Giovanni Rufino/The CW

Even though Blair wore white to her wedding to Prince Louis, it was still surprising to see her be a little edgy and wear a blue dress to marry Chuck.

25. Penn Badgley And Blake Lively In “New York, I Love You XOXO” (S6:E10)

Giovanni Rufino/The CW

Only Serena would be able to pull off a gold wedding dress.

And Don’t Miss Out On The Chance To Own This Outfit, Worn By Leighton Meester!

Click here for the opportunity to proudly call this beautiful ensemble your own.

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