For all of it's many outdated outfits, Gossip Girl just has a certain retro charm, a certain style that, in the context of the film, looks timeless. This is a breakdown of the best (and the worst) outfits as well as an account of Blair Waldorf's makeup style.

Best Outfits of the Show

How can I start to tell you all about the iconic character's aesthetics, without showing you exactly what I mean? Below is a list of the outfits of the show that stuck with me, that I will try to emulate in the below sections.

1. Blair in Black and White
2. This Minidress
3. This Victorian-Doll Dress
4. This Glamorous Outfit
5. The Vera Wang Pilot Dress
6. This Houndstooth Blouse
7. This Golden Masterpiece
8. This Lacy Floor-Length Gown
9. This Red Minidress
10. This Classic Black Dress
11. This Boho Outfit
12. This Goth Masterpiece
13. Yet Another Little Black Dress
14. This Adorable Preppy Piece
15. This Plaid Set
16. Another Plaid Set
17. Dark Lips Look SO GOOD On Jenny
18. This Eyeshadow Look
19. This Edgy Outfit
20. This Headband and Dress Set
21. This Met-Gala Esque Silver Dress
22. This Preppy Masterpiece
23. Yet Another Jenny Humphry Outfit
24. The Interview Outfit
25. The Epitome of Blair Waldorf
26. Serena's Hair Here!!
27. Jenny's Minidress!
28. Serena's Messy Prep School Vibes

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And.. Exactly What We Don't Mean:

1. Chuck.. Oh God.

2. This.. Very 80s Look

3. No One Under the Age of 60 Should Be Caught Wearing Leopard Print

4. Taking the Messy Look a Bit Too Far, Serena!

5. She Looks Like a Child Trying to Be Punk.

6. When Jenny Went Wrong, She Went Very Wrong.

7. Blair Looks Like a Children's Museum

Blair Waldorf: A Style Analysis

Blair is considered the fashionista of the group, and for good reason. If Blair is good at anything, it's coordination. Every outfit of hers clearly took hours to plan, and it gives off the impression of her being a primped up doll, the epitome of well thought out perfection. She loves to match colors, often using a headband or other hair accessory to match her clothes.

She wears her hair in tight waves, making sure to give it volume and avoid flyaways. She adores jewelry, but more subtley than Serena: accessories you'll often see her wear include pearl earrings, scarves, gloves, or a single necklace. Think Audrey Hepburn or Chanel. She knows how to mix glamorous with refined elegance- when she does wear something dramatic, she keeps the rest simple.

But perhaps the single most noticable thing about her is her makeup. Her lips are unique and shiny, almost flawlessly so, and her makeup, like everything else about her, has a dollike nature. She keeps her blush on the apples of her cheeks, and maintains long, curled lashes. She avoids dark makeup, instead choosing colors that, while not necessarily natural, are only a few shades darker than they would be naturally.

My Impression of the Character's Looks

• Jenny. Unpopular opinion, but Jenny is my favorite character on the show, fashion wise. I've always loved bold looks, and in a society filled with subtley and natural looks, she knows how to stand out in a good way. Her dark lips and eyelashes complement her pale hair perfectly, and her silent stare gives off the impression of a haunting, gothic kind of beauty. And honestly, I loved her hair extentions, I don't care what anyone says. I think there were times when she took the look too far (as all fashion designers do), but she looked best when she wore simple, statement pieces. That said, she knows how to do more light feminine looks too: in fact, her looks in the first few seasons, before her transformation, did preppy better than Blair Waldorf herself!

• Blair. Blair obviously has very good dress sense, if at times a bit too refined and put-together for my taste. While I (of course!!) appreciate her nods to Audrey Hepburn and Chanel, my favorite looks are the ones that seem almost effortless (but aren't), something Blair has never once tried to do. Plus, I appreciate a nod to the dark feminine every now and then. Overall, while Blair's dress sense is obviously well defined and objectively wonderful, it simply isn't the same as mine.
• Serena. Serena really did always hit or miss with her looks. They're very, very 2000s, both the good and the bad, but to be honest it's hard to review her looks, because most of these outfits are considered dated and tacky today. That said, she always looked good in them, knew her colors, and gave off a free-spirited vibe- plus, no matter the era- I can always appreciate a good leather jacket. If anything, Serena knew how to look effortlessly beautiful, how to look like she didn't try at all, and I appreciated her bohemian aesthetic.

• Vanessa. Look, I do understand what they were going for, I do. That said, the hair extentions were so awful, so obvious, so frayed that it ruined every outfit she had with the extentions. Vanessa really did fade into the background with her outfits (sad, considering how beautiful the actress is), and to be honest she didn't even really do the girl-next-door thing right. Girl-next-door is still supposed to look good on you, just in a casual, effortless way. They could have made just a little bit of an effort to make us notice her.

Love it or hate it, you can't deny, Gossip Girl made headlines in the fashion world. Serena and Blair were complete opposites, yet somehow, their styles seemed to highlight their personalities. Let me know in the comments whose character you thought had the best fashion sense (and the worst.)