Finding Carrie Bradshaw’s Most Heinous Outfit Of All Time

carrie bradshaw dior ugly

We’re taking Sarah Jessica Parker‘s birthday week very seriously over here, in case you were wondering. Her most famous character, one Miss Carrie Bradshaw is a fashion icon (as is Parker in her own right), and Sex and the City was, for better or worse, a formative show for all of us over here.

Later that day, I got to wondering about Carrie Bradshaw’s style choices and how she became a fashion icon in the first place. From my point of view, she would grab everything from a box of costumes from a canceled Broadway production and call it an outfit. Are we all just blind? Is Bradshaw’s fashion icon status an elaborate prank on all of us? What is the nature of time and space itself?

Let’s go through some of Carrie Bradshaw’s worst sartorial moments, and pick the definitive winner (or loser).

1. The Elongated, Stuffed Peplum Of Our Nightmares

carrie bradshaw rose peplum dress

What do you think she has in there? Cotton candy? Tissue paper? Furniture batting?

2. The Cowboy Hat/Crop Top From Hell

carrie bradshaw cowboy hat

The arm band really makes this poetry.

3. Pamela Anderson’s Wedding Dress

carrie bradshaw ugly gold flower dress

Eat your heart out, Georgia O’Keefe.

carrie bradshaw dior ugly

A t-shirt and extremely long, extremely poofy skirt is the optimal choice for a day at a crowded open air market.

5. That Tie. That Hat. Help Me.

carrie bradshaw horrible hat

Jaunty! Excuse me, I need to be revived by a doctor.

6. SVU’s Version Of A Streetwalker

carrie bradshaw ugly outfit

So, that’s a velvet tube top and underpants, right?

7. The Fanny Pack Chronicles

carrie bradshaw worst outfit

Make sure you don’t miss out on that hat she’s holding in her hand. This woman rivals Christina Aguilera in terms of jaunty hats.

8. The Cinched Waist

carrie bradshaw midriff belt

I guess we should all be really impressed by her commitment to her cinched waist.

9. The World’s Least Powerful Power Suit

carrie bradshaw pink white suit


What fuckery is this? She looks like the butler at a children’s tea party.

10. That. Belt.

carrie bradshaw ugly outfit

I guess a bra would be too much to ask for once you’ve picked that belt out.

Which outfit do you think is the most horrifying?

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Photo: Sex and the City (HBO), Sex and the City (2008), Sex and the City 2 (2010)

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    • Samantha Escobar

      #6 hahaha. Not the worst one (I voted #8) but SVU’s version of a streetwalker made me laugh.

      • Hayley Hoover

        I also LOL’d. Nice one, J.

      • Julia Sonenshein


    • Lindsey Conklin

      MY top three worsts are winning. OMG THEY ARE ALL SO BAD. I will hand it to the woman though, killer abs!

    • Ashley Reese

      There are all so hideous…and she looks like MusicEra!Madonna in that one music video with that cowboy hat.

      LOL at the SVU reference.

    • CMJ

      I still can’t get that horrible headband she wore to her birthday party ((35th?) out of

    • Kaitlin Reilly

      The belt around her stomach makes NO SENSE.

    • Ly

      The fanny pack and the skirt look a bit like an american flag when paired, so…. points for patriotism?

      • Julia Sonenshein

        USA! USA!

    • I Like Pizza

      I simply cannot choose, and I’ve never even watched this show.

    • Katie

      I never noticed she had such amazing abs.

      • Elizabeth Licata

        Me neither!

      • itpainsme2say

        Really I always saw her as a classic example of butter face

    • JennyWren

      I love how most of these are fails simply because they inverted the Coco Channel rule. Instead of taking one item off before finishing up, Patricia Field was all “How about that hat that intern is wearing? Fuck it, why not!”

      I must admit though, I kind of like the poofy skirt/Henley shirt combo. But I would want to tone both individual items down considerably.

    • Cate

      I’m going with the elongated stuffed peplum just because that is a very nice outfit until you scroll down and realize that no, it is not a lovely, late 50s/early 60s style dress, but is instead an EYE-BLEEDING HORROR.

    • Nicole Hernandez Froio

      Oh my gosh the cowboy hat and the weird tiny tube top I CANNOT. that wins in my book, but the cinched waist is a pretty close second.

    • Daniella Sloane Alberts

      i really like #10 but w/ different shoes.

    • Jobeans

      7 and 10 both feel on trend today. Also, I am frustrated that I cannot find one of my least favorites doing image searches right now and that I am awake at 12:50am looking for it! It’s the one where she wears a white loose fitting tube dress with an awkwardly large belt at her hips (i think) and that giant terrible butterfly necklace that makes it look like a really weird halter dress. *cringe*

      I think it’s from the episode “what comes around goes around”

    • Amanda

      While all of these are so horrifying that I feel the need to cleanse my eyes, that CINCHED WAIST. WHY DO YOU NEED TO CINCH YOUR ACTUAL WAIST SANS FABRIC WITH A BELT? WHY?