Carrie Bradshaw’s 10 Most Iconic Looks From ‘Sex And The City’

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Asking a Sex And The City fan to choose their favourite Carrie Bradshaw looks is a hard ask.

How can one possibly choose from a catalogue so vast and varied? How can one distinguish between the ‘I love that, I’d wear that’ looks and the ‘that is deranged but iconic’ numbers?

Should I include less memorable looks, like Carrie’s ‘I’m dating a politician’ tan trench? What about the metallic green mini skirt that looks excellent from the front, only to reveal a truly shocking white bustle from behind? What about the tutu and BONDS chesty from the title credits? 

For the sake of this article, I’ll simply call these my honourable mentions, and get on with it. (The rules here are as follows: Original series only. No spinoffs or movies included.)

Finding a hi-res image of this dress? Impossible. (Credit: HBO)

1. The Lunch-With-Big Pink Dress

This dress does not get the love it deserves.

Carrie has never looked better than in this episode. The hair, the make-up, the vibrant pink dress: she looks like a tiny pastel fairy, destined to bring colour to the corporate lunch crowd at Eleven Madison Park.

Let’s just say, Najinsky could never.

Probs not a great look to wear white and show up to ex’s engagement party unannounced. (Credit: HBO)

2. The Bias-Cut Dior Slip

Hmm, what to wear to cocktails with the girls, followed by a casual pitstop at your ex’s engagement party? A Dior slip dress, of course. This simple but beautiful dress has been dubbed by some as a ‘revenge’ dress and, if she didn’t look so amazing, we’d probably be much more critical of her turning up to an ex’s wedding event in white satin. Rude.

THE newspaper print dress. (Credit: HBO)

3. The Dior Newspaper Print Dress

Even fringe fans of the series are likely aware of Carrie’s newspaper print dress. Designed by John Galliano for Dior, the dress (like the designer) is a little problematic. It appeared in the Dior spring/summer 2000 collection, and was allegedly inspired by those sleeping rough on the streets of Paris and 1920s balls at which rich people would dress-up as the poor. (What?)

In Sex And The City, Carrie wore the dress to stalk Natasha at lunch after the whole Big affair. Probably not the most humble look to meet the woman whose life you destroyed–but an iconic dress, nonetheless. 

Vivienne Westwood sure knew a silhouette. (Credit: HBO)

4. The Vogue ‘Corporate Cosplay’ Suit

Carrie is actually a cosplay queen. Any excuse for a drag moment, and she is there. There was her Jackie O era, the candy striper look, the head-to-toe black and white stripes for Paris: Carrie loves an opportunity to go camp. 

In this episode, she gets an invite to work at Conde Nast HQ, so naturally, this freelancer goes full ‘corporate drag’ to visit the office, donning a phenomenal, form-fitting, pinstripe skirt suit by Vivienne Westwood. It’s stunning and it’s perfect.

Special shout-out to the now famous (not an “urban shoe myth”) Manolo Blahnik Mary Janes.

Free designer clothes? Not a bad date… (Credit: HBO)

5. The Pink Oscar De La Renta Dress

While reading ‘poetry’ (i.e. fashion editorials) to her new beau, Carrie name-drops an Oscar De La Renta pink dress–which he subsequently buys her to wear on a date to the ballet. (Because that’s a thing that happens to everyone, right?)

Another gorgeous pink number (is there a pattern here?) the dress is a work of art that only Carrie could pull off.

Who looks *this* good in *this* outfit? (Credit: HBO)

6. The Little Grey Dress

I’ve seen this dress referred to as an ‘LBD’ but… it’s grey, right? (Am I crazy?!)

Either way, it gets a mention here for one key reason: Sarah Jessica Parker looks hot as hell. How does she look so good in this fairly basic ensemble?

Only in TV-land could a person chuck on a grey body-con mini, pair it with stilettos and aviators, and look normal, nay, fantastic.

Nothing like a little half-way cosplay to spice things up. (Credit: HBO)

7. La Doleur Exquise bondage combo

Oh, Carrie. This is the first of two cosplay catastrophes in this episode. (The second being when she visits Big upon his Paris return, donning a beret and enthusiastically presenting ‘le filet o fish et le French fry’. Poor Carrie. So cringe.)

I, however, love it. Firstly, we rarely see Carrie in black.

Secondly, Carrie loves to toe the line between sexy and slutty. While Samantha will go the full hog, and Charlotte not at all, Carrie likes to do a high-low thing where she’ll pair a weirdly Victorian black midi skirt, with a barely-there backless party top. This is also the epitome of ‘early series Carrie’, who wore whatever she wanted within her $20 thrift shop budget. 

Thirdly, it’s iconic. What else can I say.

It was good while it lasted. (Credit: HBO)

8. The Dolce & Gabanna ‘Heidi Klum’ dress

I was unsure whether to include this since it’s not Carrie Bradshaw’s own styling, but… it’s just so pretty! Unfortunately, in this episode, Carrie is forced into a reverse-butterfly situation, where her stunning gown is downgraded to an electric blue trench and bejewelled panties (another honourable mention for the list) while Heidi Klum is handed this beautiful floral number.

Also, if you don’t see this dress and immediately hear Alan Cumming saying “Trot, love. Trot”, you’re due for a rewatch.

Bring back the mismatched Louboutins on ‘And Just Like That…’ (Credit: HBO)

9. The LA Mismatched Shoe Moment

Like many Carrie Bradshaw fashion moments (e.g. the flower corsages, the visible bras, chunky gladiator heels) this mismatched Louboutin shoe moment became an accidental trend. Although, as with many Carrie looks, what looks effortlessly chic on her can look a little contrived and confusing IRL. So, that one died out pretty quickly. Nevertheless, I’m betting on a resurgence…

One dress to rule them all… and it’s the Versace ‘thousand layers’ gown (Credit: HBO)

10. The Versace ‘thousand layer’ dress

Ah, but of course.

For a dress that never got worn outside her hotel room, this gown remains one of the series’ most iconic outfits. So much so that it earned a cameo in And Just Like That….

Designed by Versace, the ‘mille feuille’ or ‘thousand layers’ dress is classic Carrie in its impracticality (reminder: it was intended for Carrie’s first night out in Paris, where she was presumably just going for dinner, right?) but, according to designer Pat Field, was chosen to reflect the many complex layers of Carrie’s relationships.

Stream all seasons of Sex And The City on BINGE, here.

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