If you comb through Kim Kardashian West’s Instagram account, you’ll notice that her feed is filled with haute couture looks and expensive designer outfits for every occasion. The once aspiring stylist, turned reality-television star and all-around mogul never did quite fulfill that dream — but she certainly kept her love for fashion alive over the years. She’s even appeared on the cover of many fashion magazines, including Vogue.
In the last few years, especially after she began her relationship with rapper Kanye West, she has been in almost all of the best-dressed lists at any event she’s attended, and rightfully so. She’s really upped her fashion game. For the most part, her style is pretty much flawless, and her ensembles are always on trend, or trend-setting. However, it wasn’t always this way for Kardashian West. Everyone’s got to start somewhere, and unfortunately for Kardashian West, her beginnings weren’t always all that great. Though she’s certainly come a long way since her rise to fame, her near-flawless image doesn’t take too kindly to her questionable past outfits. Let’s take a stroll down memory lane and see some of the looks she probably wishes she could bury forever.
15 Whatever Is Happening Here
Now, it’s not fair to put people at a higher standard, simply because they’re celebrities, but it’s difficult not to critique someone who boasts about having an extremely stylish image. Granted, this photo was likely taken during the hight of American Apparel’s popularity, so technically, Kardashian West is in style, but those leggings against that black bodysuit sort of makes the bodysuit look like a diaper.
Also, not even a classic pair of Louboutin heels can save this look — especially with those yellow leg warmers sitting right on top of them. There are just so many elements of this outfit that are downright wrong, it’s hard to break it down and dissect it all. Perhaps we can just assume that Kardashian West wore this ensemble to a costume party?
14 When She Stepped Out In These Shoes With Swollen Feet
Pregnancy can be a very beautiful time in any woman’s life, what with the bringing a new life into the world and all. However, pregnancy isn’t always sunshine and rainbows. There can be many difficult aspects to pregnancy that affect a lot of women, making their nine months carrying a child quite uncomfortable. A lot of women focus on their health and comfort during this time, and while it might mean making different style choices, like avoiding high heels.
However, for Kardashian West, giving up her pre-pregnancy style was not an option. She seemed to be unwilling to make any changes to her lifestyle, at least in terms of fashion, when she became pregnant with her first child, North West. This is why she stepped out with her feet bursting out of her shoes, because her feet had become so swollen, but she refused to wear different shoes.
13 This Poor Choice In Trousers
While people should be allowed to wear whatever they want, regardless of whether or not they’re a public figure, Kim Kardashian West certainly received a lot of critiques for this body-hugging outfit, particularly, the high-waisted trousers with a peplum. Kardashian West is typically known for her form-fitting ensembles, but a lot of people said that these trousers were not a great choice for her curvy body type.
Truthfully, she’s made worse fashion choices in comparison to this outfit, so it’s tough to critique it. And again, anyone should be able to wear whatever they like, regardless of what their body type is, so long as their comfortable. on could argue that because Kardashian West has a whole glam squad under her employ, that if she makes questionable choices in terms of her style, it’s probably her stylist’s fault.
12 The Outfit That People Compared To Sea Life
This outfit is a tough one to judge, as Kim Kardashian West wore it while she was pregnant. Again, when a woman is with child, it’s usually not the best time to judge their fashion choices, because it’s safe to assume that a lot of what they wear is about comfort. From the front, this dress looked just fine, but people were quick to critique the look from the side.
Because of the overlay, the dress may not have been the most flattering from the side, but of course, people were quick to come at her with insults, calling her Shamu, the killer whale. Again, she was pregnant when this photo was taken and she wore this outfit, so it isn’t really fair to call her names that are specifically about her weight.
11 This Ensemble That Looks Like It's From A Bargain Bin
While Kardashian West’s style is pretty solid now, we can’t be too tough on her, because she rose to fame at a time where fashion was generally questionable anyway — whether or not you considered yourself stylish. However, regardless of that fact, Kardashian West certainly wouldn’t post this photo as a “Throwback Thursday” on Instagram any time soon. The brown, matchy-matchy accessories are a great start, especially when one of those pieces is calf-length leggings — not very flattering at all.
Then there’s this tunic dress situation that she belted (not with a brown belt, surprisingly), seemingly to show off her figure. However, she somehow still ends up looking shapeless, perhaps because of the busy, striped design of her tunic. The sunglasses indoors is also a interesting touch for a red carpet event.
10 This Matchy-Matchy Look With Former BFF And Employer, Paris Hilton
Oh, dear. Where do we begin with this one? This photo was taken before Keeping Up With The Kardashians was anyone’s favourite guilty pleasure. At the time, Kim Kardashian West was working as socialite and reality star Paris Hilton’s personal assistant, and while she was technically her boss, Kardashian West also travelled and partied with Hilton as if they were BFFs. The friendship certainly earned her some popularity, as Hilton was something of an it-girl at the time, and paparazzi were following her around everywhere. It’s one thing to coordinate with your friends, but these two were straight-up matching, down to their oversized, metallic, Louis Vuitton purses. Kardashian West even took it a step further and matched her swimsuit to her purse as well. Also, note that she’s wearing flip flops. That’s likely something she’d never be caught wearing now.
9 This Very Wild Outfit
It’s getting wild over here right now. In this photo, Kim Kardashian West looks like she’s stepping out for a casual stroll in a head-to-toe cheetah print ensemble. If that weren’t bold enough, the outfit looks to be faux patchwork cheetah print palazzo pants. While the rest of the look (aside from that very fringe-y bag) are quite understated, the large print is just a lot of the eyes to process. It’s such a busy pattern, that it’s hard to look away from it, even though all you want to do is not look at the outfit anymore. While she has perfected the monochromatic look lately, cheetah print is not something you want to treat as a head-to-toe “monochromatic” look, and this outfit is absolutely proof of that fact.
8 This Saggy Ensemble
Maybe she needs to take another x-ray on Keeping Up With The Kardashians, but the debate about whether or not Kim Kardashian West’s rear end is real or fake continues to rage on as the years go by. Of course, whenever there’s any evidence pointing to it being fake, everyone jumps at the chance to prove once and for all that her derriere isn’t natural.
When she stepped out in this leather skirt, people were quick to point out that it looked as though her backside was deflating, as she pulled up her skirt. People also noted that they were unsure if it was the skirt or her actual body that looked more like a full diaper than someone’s rear end in a skirt. Whatever the actual reason was for her skirt to look that, we still have no idea whether her backside is natural or paid for.
7 Is It Just Me Or Does She Look Like An Elf From The Medieval Era?
As kids would say it, “What are those?!” This is a terrible outfit for a number of reasons, but let’s start from the bottom up, shall we? First, those shoes. Boy, are those shoes pretty awful. They’re like UGG boots, but not quite, and it looks as though they’re studded as well. And then of course, there’s the matching belt and purse again.
While Kardashian West has never claimed to be vegetarian or vegan, and often wears furs and leathers, it’s quite a sight to see a crocodile belt in the shape of a crocodile. Then there’s her unkempt ‘do, which doesn’t necessarily look bad, but because she’s such a stickler for her image looking airbrushed and perfect now, that it seems really our of character to have a hair style that doesn’t look like it was worked on for an extended period of time.
6 This Now Infamous Bikini Shot
Kim Kardashian West was recently photographed while on vacation with her family. While she should have just been out having a good time with her children, she was instead too busy defending herself against people who were saying that this photo is proof that her famous derriere is indeed, fake. For years, people have been speculating that her greatest asset is in fact, not natural — despite the fact that in an episode of their reality show, Keeping Up With The Kardashians, she took an x-ray of her booty to prove to naysayers that she was born with everything she’s got. However, since then, her booty seems to have grown at an alarming rate, and so people have been looking for proof that she’s had work done. They considered this photo solid evidence.
5 This 2000s' Disaster
In Kim Kardashian West’s defence, the 2000s were not the best time for fashion, whether you were famous or not. However, she seemed to really have a thing for button-down shirts, sweater dresses and tunics, as well as belting everything with matching purses and shoes on the red carpet. This outfit is interesting, because it’s difficult to tell whether she’s attending a red carpet event, or going in for a job interview. The most notable thing about this outfit, is that upon closer inspection, there just is not a lot to be done by way of improvement, because it just seems so bad. Perhaps the aversion isn’t so much towards this outfit in particular, but what it represents, as we were all likely fashion victims in the 2000s — this photo of Kim Kardashian West is just a painful reminder of that fact.
4 The Dress That Had People Comparing Her To A Couch
To be fair, this look is now iconic in its own right — even if it’s just for all the memes that were made because of it. At the 2013 MET Gala, Kim Kardashian West wore a very very floral gown. People thought it was so bad that they dubbed it “the couch dress,” and compared it to Mrs. Doubtfire.
The best part about this outfit, is that while she may have regretted the dress choice, she eventually gave in and had a laugh about it herself. In 2015, she wore the dress again, this time, for Halloween. When she posted it on Instagram (because of course she would), she captioned the photo, “I think I nailed the Kim K costume!” Now if dressing up as yourself isn’t peak fame, I don’t know what is.
3 These Poor Accessory Choices
She seems to really like her sunglasses! The combination of her sunglasses, large hoop earrings, and initial necklace — all worn together — just seem to scream early 2000s. This photo also seems to be taken before she had her baby hairs removed using laser hair removal — a procedure she famously got to achieve that mannequin-esque look she’s got, with not a hair out of place (literally).
The babydoll dress all screams teenager at her first girl/boy party. Granted, she was a lot younger then, so perhaps her style just hadn’t quite matured yet, but it’s doubtful that she kept any of these pieces in her archives to use as a “vintage” piece, even ironically. Once she began dating Kanye West, he reportedly got his stylist to come to her home and sort through her closet, getting rid of everything that wasn’t stylish anymore.
2 This Menswear Inspired Getup
Now here is another case of failed edginess. Women’s fashion has created many iterations of the menswear-inspired look. A lot of the time, these outfits channel a but of glamour and androgyny, and are usually really appealing. Unfortunately, Kim Kardashian West’s attempt here didn’t quite translate. Instead of the over-sized pieces she sometimes wears now, this look just seems like it’s a little bit ill-fitting, making it look more frumpy than glamourous.
Again, the large purse just seems like it doesn’t belong on the red carpet, and it makes her look as though she’s going out for after-work drinks with her office mates than going to a celebrity event. Frankly, it’s not one of the worst looks she’s ever worn, but it may as well be, because it’s just really boring.
1 This Plastic Situation
Celebrities have done some outrageous things in the name of fashion. There was Lady Gaga’s meat dress (along with almost all of her other red carpet looks), Lil Kim’s purple pasty, Rose McGowan’s see-through dress, and a whole list of others. It seems like Kim Kardashian West might have been trying her hand at a haute couture look with what can only be seen as some sort of DIY project using plastic cups from a party the night before. It’s always good to up-cycle materials when you can, for the sake of the environment, but perhaps this look was better left in the recycling bin. Perhaps she was trying to be edgy, but unfortunately, the look didn’t quite translate. In theory, the look might have been better with a different material, but that just wasn’t the case.
