Kim Kardashian: Her 24 Most Hideous Fashion Moments
Mia Cox
Updated on March 15, 2026
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
1Let 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
2I remember this sartorial phase well. I thought bold shapes from INC were all the rage. I was mistaken.
People’s Choice Nominations 2007
3That 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
4Bodycon 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
5Future Kim would like to know B) Is Kanye there? A) why are you wearing that?
Trump Vodka Launch Party at Les Deux
61) 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
7Bodycon turtleneck dress = All the rage at Express
Ironically, Kim Attended The 2007 “What Teens Want Party”
8Remember that episode when she became obsessed with Kylie’s Tumblr style? Kylie was 15 at the time…
Nicole Romano Fall 2007 Fashion Show
9I 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
10Let’s talk about that crimp, Kim. Nevermind the slip dress.
Nintendo Wii Game Console Party
11Another satin shirt for the books, paired with (light pink?) stilleto boots. So 2006.
LA Kings Game
12More satin. More slip dress. And open-toe white heels.
HelloTheseAreMyBoobs #2007
13When Kim’s birthdays were celebrated at adorable little venues, like Les Deux.
Make Sure You Guys Vote, OK?
14Casualwear, because Democracy!
When The Kardashians Collaborated With Bebe
15Yep, that is a corseted dress with a hood.
Intermix/Vh1 Rock Honors VIP Party
16I bought a bag from Target in August 2005 that looked just like this dress.
Whatever, Take My Picture
17Don’t lie. You had some version of these wraparound shades.
Bongo Fall Collection Launch
18I have nothing to say about this (I have so much to say, but it’s impossible to verbalize).
William Rast Spring 2007 Fashion Show
19Remember when mini blazers and jeans made up your standard “going-out” outfit? YOUTH.
‘Somebody Help Me’ Premiere
20Knit dress + white boots + boobs = 2007 Kim Kardashian.
Prive Las Vegas
21Where it all started: hosting parties in Las Vegas.
‘sTORI Telling’ Book Launch at Kitson LA
22“Hey guys. Can’t pose for long. Gotta go play with my T-Mobile Sidekick.”
TRL 2008 Appearance
23“Hey guys, it’s Princess Kim Kardashian.”
