The 23 Cutest Outfits Ever On Sex And The City

When it comes to Sex and the City’s fashion, everyone has a different opinion. Some people swear by short-haired season 4 Carrie, others are obsessed with Charlotte circa her wedding to Harry. So to choose the greatest outfits, I consulted with five of my stylish (and very distinct) coworkers-slash-SATC-addicts, Ella Ceron, Koty Neelis, Rachel Hodin, Jamie Varon, and Brianna Wiest. Here are our picks, and why we love them (in no particular order).

1. The Classic Carrie


Brianna: It’s the classic. It’s the SATC staple. I love it because back when she wore it, nobody else was wearing tulle like that. It was decidedly out-of-current-trend and she chasséd down the street like she just didn’t give a damn. That’s what I love most about Carrie and what I’ve tried to emulate from her: she does what she wants and she doesn’t justify it.

2. Carrie’s Rainbow Coalition.


Jamie: Carrie might be the only person who can pull off the “I WORE EVERY COLOR IN THE RAINBOW” look. She just embraces color in the loveliest way and it inevitably wants you to run out to the nearest store and buy a rainbow striped skirt and call it a damn day.

Chelsea: OMG yes I love that outfit.

3. Samantha’s (Movie) Hat.


Brianna: I know we’re not doing the movies but we have to make an exception for this hat because I aspire to wear that size hat, in all seriousness.


4. The Carrie Fairy Tale Ending Dress.


Jamie: Carrie looks like a ballerina on her way to a job interview in which she forgot to change out of the bottom half of her outfit and IT IS WORKING. I had never before considered a tutu to be a viable clothing choice to be worn outside of a ballet studio, but Carrie manages to make this look not only not totally weird, but actually so beautiful.

Ella: The fact that this one mirrors the thousand-layer dress is a nice little detail.

5. Charlotte’s Elizabeth Taylor Dress.


Chelsea: This is still my favorite Charlotte outfit, obviously because it’s beautiful and the story behind it is moving/inspiring, but also because I feel like Charlotte rarely got the dramatic “outfit entrance” moments that, say, Carrie got, and she deserved them.

6. Miranda’s Black Mesh.


Chelsea: This is a very good Miranda moment, which obviously did not happen that often. I would argue that she looks better than Carrie here.

Ella: It’s very Rihanna circa now. And Nicki’s doing a lot of black mesh right now, too.

Jamie: YES I LOVE.

7. Carrie’s Crop Tops.


Ella: Crop tops are having a moment, sure, but Carrie (so really, SJP) has had abs forever and ever, and you can’t hate her for it. If I had that stomach, I’d be tying up my blue gingham, too. If I had that stomach, I’d be wearing a fanny pack, too. I can’t hate it. I want to hate it, because I’ll never have that stomach (I like pizza too much) but I can’t hate it.

Koty: Carrie makes me think of all the cute outfit options I would have if I had abs.

Chelsea: Same.

8. Charlotte’s Crispest White Dress.


Koty: With Charlotte’s style it was all about the subtle details. Her classic style had a refined elegance none of the other girls could quite pull off.

9. Carrie’s Simplicity.


Rachel: Obviously she was known for her loud, “statement” pieces, but I always thought she looked the best in a simple understated dress like this. The nude silk dress looked so good with her pallor!! And with the Carrie nameplate necklace.

Koty: She looked so good in these simple dresses.

10. The Carrie “Thousand Layer” Dress.


Ella: I am not a ballgown girl, but something about being surrounded by layers and layers of fabric has always appealed to me somewhat. Like, what girl secretly doesn’t want a princess dress like that? You could wear it absolutely nowhere, but it just seems like if you have to wait for some eccentric Russian lover in a suite in Paris, you might as well do it in this dress.

11. Samantha’s Little Red Look.


Chelsea: Samantha’s look when she meets Mr. Cocky in the street is my favorite Samantha. I believe it may be the most fully realized Samantha look.

12. The Girls At The Ball Game.


Ella: How I would like to attend every baseball game ever, amen.

Rachel: Just generally enjoy everything going on here, especially Miranda’s glasses.

13. Carrie’s Bowie Shirt.


Rachel: Carrie is so young here. and I love a young Carrie. So much more than the older Carrie who thought it was a good idea to do a sequel. The only thing I love more than a young Carrie is a young Bowie.

Koty: I love the way she looks in the early seasons. She used to wear red nails all the time but then I think they stopped doing that after season 2.

14. Charlotte’s Confusing Pink Coat.


Koty: I don’t really understand this coat or the pastel blue purse but somehow she looks adorable.

Chelsea: Carrie gets all the “weird outfits that are somehow cute” credit, but I think Charlotte was actually the secret winner in that category.

Rachel: Her coat is very Prada this season.

15. The Girls In Los Angeles.


Brianna: 1. Miranda rocking the classic LBD, 2. Carrie’s bicolor shoes, 3. Samantha as an entity.

Koty: That is a great shot.

16. Carrie’s Bounce Dress.

Koty:The only way this dress can be properly talked about is by an accompanying gif, because this was so perfectly cut to Carrie that everything bounced just right. No one could pull this off except for Carrie/SJP.


17. Miranda’s Power Suit.


Chelsea: My favorite Miranda might be the Lean In, HBIC Miranda. I love her looking exasperated in a really conservative skirt suit.

Ella: Yes.

18. Carrie’s Traipsing-Around-Paris Outfits.




Koty: I love the scenes of Carrie exploring the city of Paris by herself, especially ending up in a cafe smoking cigarettes. I’m usually not one for giant polka dots but Carrie pulls this off in a way only she can and her hair looks amazing.

Chelsea: I’m obsessed with the blue coat and little fur hat personally, I remember being literally breathtaken the first time I saw it. She looked like a princess doll I would have played with as a little girl. (Also confession, I later bought a baby blue coat with an eggshell fur collar specifically as an homage to this look.)

Koty: We need to talk about the umbrella look though. Those boots. That pink bustier. The red umbrella. The straightened hair. Everything about this look is on point.

Ella: That’s how you wish you could look in the rain.

19. The Bridesmaid Look.


Brianna: I’m always a fan of all neutral everything. So even though the marriage was crap, the bridesmaids dresses were on point

20. When Carrie Meets Aidan.


Chelsea: This is my all-time favorite Carrie look, I think. She looked so feminine and lovestruck and flirtatious. She’s like a human cupcake!

21. Samantha’s Pink Wig


Jamie: Because, seriously, this is how you kick cancer’s ass.

Chelsea: YES. See also: Smith.

22. When Carrie Kissed A Girl.


Koty: I love this look because it’s quintessential Carrie Bradshaw. Everything from the hair, the dress, gold boots, and cigarette in hand. Plus, you can’t forget the trend Carrie started when she started wearing large flowers on her outfits.

23. Miranda’s Wedding Dress.


Chelsea: I love Miranda’s wedding dress more than maybe any other SATC wedding dress just because A) It’s so perfectly Miranda, and it looks so beautiful on her, and B) Miranda got shafted the entire series when it came to fashion, and it was lovely to see her in something that was still “her style,” but allowed her to be a little more feminine and warm. Plus her hair and makeup was, finally, on point. Thought Catalog Logo Mark

featured image – Sex and the City

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

Keep up with Chelsea on Twitter

More From Thought Catalog