news | March 15, 2026

Kim Kardashian: Her 24 Most Hideous Fashion Moments

On May 3rd, Kim Kardashian and husband Kanye West were crowned by Vogue Magazine as the 2016 Costume Institute Gala’s best-dressed couple.

It wasn’t always the case for Kimmy, though.  

At one point, she could have served as the poster child for Bebe, Wet Seal or Macy’s junior section.

We’re talking hoops, faux Missoni knits and stiletto boots found in most Nine West stores circa 2006.

For those of you who graduated college in or around 2005, prepare yourself for the most painful trip down memory lane.

Because before there was Arty Kim, there was Bebe Kim.

Rock & Republic Spring Collection Party 2006

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The Hollywood Gossip
(Getty Images)

Let the record show that Kim was billed by Getty Images in the photo description as a “celebrity stylist.” Left out, unfortunately, was her other claim to fame: Nick Lachey’s one-time movie date.

‘SiCKO’ Special Screening

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'SiCKO' Special Screening
(Getty Images)

I remember this sartorial phase well. I thought bold shapes from INC were all the rage. I was mistaken.

People’s Choice Nominations 2007

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People's Choice Nominations 2007
(2007 Getty Images)

That is….a scoop-neck dress that falls conveniently below the boobs, paired with a crisp shirt featuring poofy-sleeve detail. I owned a similar blouse from Anne Taylor.

Miami Swim Week 2007

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Miami Swim Week 2007
(2007 Getty Images)

Bodycon dress jokes aside, Kim looked insanely amazing in this photo, taken at Ashley Paige’s fashion show as part of Mercedes Benz Fashion Week: Miami Swim. Kardashian and her two sisters shot a campaign for Paige at Joe Francis’ Mexican villa, which was featured on an early episode of ‘Keeping Up With The Kardashians.’

Jay-Z’s ‘Kingdom Come’ Album Launch

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Jay-Z's 'Kingdom Come' Album Launch
(Getty Images)

Future Kim would like to know B) Is Kanye there? A) why are you wearing that?

Trump Vodka Launch Party at Les Deux

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Trump Vodka Launch Party at Les Deux
(Getty Images)

1) Les Deux 2) Trump Vodka, which is currently priced at $39.99 for 1L. Also, Kim’s fur shawl, tan boots and matching bag. All of it belongs in a 2007 time capsule, to be opened by a 73-year-old Lauren Conrad.

Mercedes Benz Fashion Week 2007

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Mercedes Benz Fashion Week 2007
(2007 Getty Images)

Bodycon turtleneck dress = All the rage at Express

Ironically, Kim Attended The 2007 “What Teens Want Party”

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Ironically, Kim Attended The 2007
(Getty Images)

Remember that episode when she became obsessed with Kylie’s Tumblr style? Kylie was 15 at the time…

Nicole Romano Fall 2007 Fashion Show

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Nicole Romano Fall 2007 Fashion Show
(Getty Images)

I had a moment in my 20s when all I wore were satin numbers cinched at the waist with the biggest belt I could possibly find, thanks to the Fendi B Belt trend.

‘Keeping Up With The Kardashians’ Series Premiere

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'Keeping Up With The Kardashians' Series Premiere
(Getty Images)

Let’s talk about that crimp, Kim. Nevermind the slip dress.

Nintendo Wii Game Console Party

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Nintendo Wii Game Console Party
(Getty Images)

Another satin shirt for the books, paired with (light pink?) stilleto boots. So 2006.

LA Kings Game

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LA Kings Game
(Getty Images)

More satin. More slip dress. And open-toe white heels.

HelloTheseAreMyBoobs #2007

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HelloTheseAreMyBoobs #2007
(Getty Images)

When Kim’s birthdays were celebrated at adorable little venues, like Les Deux.

Make Sure You Guys Vote, OK?

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Make Sure You Guys Vote, OK?
(Getty Images)

Casualwear, because Democracy!

When The Kardashians Collaborated With Bebe

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When The Kardashians Collaborated With Bebe
(Getty Images)

Yep, that is a corseted dress with a hood.

Intermix/Vh1 Rock Honors VIP Party

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Intermix/Vh1 Rock Honors VIP Party
(Getty Images)

I bought a bag from Target in August 2005 that looked just like this dress.

Whatever, Take My Picture

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Whatever, Take My Picture
(Getty Images)

Don’t lie. You had some version of these wraparound shades.

Bongo Fall Collection Launch

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Bongo Fall Collection Launch
(Getty Images)

I have nothing to say about this (I have so much to say, but it’s impossible to verbalize).

William Rast Spring 2007 Fashion Show

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William Rast Spring 2007 Fashion Show
(Getty Images)

Remember when mini blazers and jeans made up your standard “going-out” outfit? YOUTH.

‘Somebody Help Me’ Premiere

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'Somebody Help Me' Premiere
(Getty Images)

Knit dress + white boots + boobs = 2007 Kim Kardashian.

Prive Las Vegas

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Prive Las Vegas
(2008 Getty Images)

Where it all started: hosting parties in Las Vegas.

‘sTORI Telling’ Book Launch at Kitson LA

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'sTORI Telling' Book Launch at Kitson LA
(Getty Images)

“Hey guys. Can’t pose for long. Gotta go play with my T-Mobile Sidekick.”

TRL 2008 Appearance

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TRL 2008 Appearance
(Getty Images)

“Hey guys, it’s Princess Kim Kardashian.”