The Most Ghastly Fashion Moments on ‘Sex and the City’: A Retrospective

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As a former Sex and the City fan, I spent plenty of time viewing the show through rose-colored glasses. But even when I loved SATC, there was always one thing about it that baffled me: its widely celebrated fashion sense, courtesy of famed oddball stylist Patricia Field. Bold and avant-garde at best, the outfits Carrie and her friends wore were more often just plain confusing. So, to commemorate today’s 15th anniversary of Sex and the City, here are a few of the all-time worst ensembles in its history, from both the original series and the movies.

The first iconic Carrie Bradshaw look. Some people will tell you that women over 30 shouldn’t wear tutus; the truth is, everyone who isn’t a ballerina or a toddler should probably steer clear.

That’s not how shirts work.

You’ll poke your eye out, Samantha. Or, more likely, some guy’s.

Remember that time when Charlotte went to the Kentucky Derby, Samantha was an extra in an MC Hammer video, and Carrie got a gig as a TV psychic, and then they all met up to drink cosmos and dish about it?

And you thought that was Carrie’s only flirtation with the turban! Alas, it was not. This time, she’s ditched the psychic inspiration for a bit of Mary-Kate Olsen.

#Menswear.

Imagine: this existed before Etsy.

Miranda, that one Madonna video called and… oh wait, no, it doesn’t want that look back. It says you can keep it.

Not sure how this happened, but let’s go ahead and blame it on Gwen Stefani.

Think this looks bad? You should have seen what happened to the other sleeve.

Samantha does Dallas.

You can have the midriff or the fanny pack. Pick one. But don’t make it the fanny pack.

Remember that time Carrie and Samantha went to Burning Man and fell in with a group of hippie Liberace enthusiasts? Yeah, they don’t, either.

OK, it doesn’t look too bad from far away, but for heaven’s sake, what is happening from the waist up?

Here’s a good test of whether your shirt is ridiculous: if it’s impossible for people to see you in it without picturing you dancing with maracas in your hands, that’s a pretty good sign.

And finally, is Carrie doing Lady Gaga’s “Bad Romance” video or her “Alejandro” video here? Weigh in on this and other important questions in the comments!