18 Images Of Kylie Jenner's Evolving Pregnancy Style

When it was first reported that Kylie Jenner was pregnant in mid-September of 2017, I’ll be honest, I didn’t believe it. As for the reason why I thought this was just a made up story to get views? Well, that was in part because Jenner had not been with her boyfriend, Travis Scott for long and also because she is only aged 20.

It’s not so much the fact that Jenner is young either, but rather that at 20, she is only starting to build her empire (which looks as though it’s on the fast track to overtaking her famous sibling, Kim Kardashian's career), so a baby didn’t seem to fit in with that. However, fast forward a few months and the claims about the youngest member of the Kardashian/Jenner household have become a lot more convincing, and this is mostly based on Jenner’s refusal to neither admit nor deny the pregnancy claims. That, and the fact that her wardrobe has changed rather dramatically in recent months.

She has gone from wearing tight and revealing clothing -- seriously, Jenner never missed an opportunity to flaunt her curves -- to a wardrobe that mostly consists of baggy T-shirts and sweatpants. And rather than breaking out the cute maternity wear, Jenner seems to be going to great lengths to hide any sign of a bump at all. Below are 18 images of Kylie Jenner’s evolving pregnancy style, and while it’s not definite proof that she has a baby on the way, it definitely adds weight to the rumors.

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18 Casual But Cute

Via HollywoodLife

Like I mentioned before, no one knows for sure whether Kylie Jenner is pregnant or not, but one thing we do know is that there has been an evolution of her wardrobe in recent months. Right before the pregnancy news, Jenner posed for a photo with a fan, and according to HollywoodLife, this photo was taken on Sept. 16.

In the snap, Jenner looks casual but cute and appears to be wearing a loose-fitted white top and a pair of leggings -- a smart choice because this would be comfortable if her belly was starting to grow. Although this image gives no indication that Jenner could be pregnant, if the rumors are to be believed then this is an early snap of her pregnancy, and it’s not surprising that no one suspected anything at this stage.

17 One Hot Mama In White

Via Kylie Jenner/Instagram

Then a few days later this photo was shared on Kylie Jenner’s Instagram account (just days before the rumors started to swirl regarding her pregnancy). This dress is still very much in keeping with the style that we had come to know and love Jenner for, and the cut is both stylish and flattering.

There’s just one small difference between this picture and the pre-pregnancy Jenner style, and that’s that this dress doesn’t show off her stomach, nor her bottom, which she has come to be particularly proud of. If she is pregnant, she would have had a very tiny bump at this stage, however, it’s interesting that in one of the last full-body photos of Jenner on Instagram, she is her wearing a dress that’s loosely fitted over her stomach.

16 The Photo That Started It All

Via HollywoodLife

For many, this photo of Kylie Jenner is the photo that started it all. It was at the time that this image was shared via Snapchat that the reports that Jenner was pregnant first started. So, what was it about this image that got fans and the media so excited about a potential baby on the way?

For starters, Jenner doesn’t look as put together as her friends Harry Hudson, Jordyn Woods and Stass, all of whom are flaunting their figures and look great in their outfits, while Jenner, on the other hand, has chosen a much more...shall we say...relaxed approach to her look. Sweatpants and a baggy top is not exactly high-fashion, and Jenner is someone who is usually celebrated for her taste in clothes, so, could she be trying to hide something?

15 The Baby Bump Reveal...Kinda

Via Kylie Jenner/Instagram

You’ll notice that the outfit in the photo above, and this one, are the same. Kylie Jenner shared this snap on Instagram to pay tribute to her best friend, Jordyn Woods, but what people were really focusing on is her choice of outfit (which is a sharp contrast to Woods).

With this snap, Jenner seemed to make a comment about her pregnancy rumors because she chose to cheekily draw attention to the side of her stomach and reveal that there was no baby bump -- although we should all remember this was a really early snap, and it’s entirely possible she was not showing at this stage.

What’s also worth mentioning is her style choice, because while Jenner has never been afraid of showing off her body, in this image she opted for bright red sweatpants and a sweater. When it comes to pregnancy style, it seems Jenner is all about comfort, and not so much about style.

14 The Oversized Shirt Look

Via Kylie Jenner Instagram

I think by this point on this list we have already established that Jenner likes showing off her body, which is why every time she decides to cover up, people notice, but we notice more than usual when we are thirsty for clues regarding a potential pregnancy. The image was shared on Instagram on Oct. 10, and because Jenner chose not to confirm nor deny the rumors involving her and Travis Scott expecting, it caused even more of a hype when she posed in the oversized oxford shirt (all the better to disguise a growing belly).

It's no secret that this shirt is too big, but it is still really cute and can be worn as a dress, which it appears Jenner chose to do in this pic.

13 White Linen, And A Clever Placement Of Her Hands

Via Kylie Jenner/Instagram

The Kardashians are baby makers; Kourtney currently has three children and has nailed her maternity style every time, and Kim also has three children (one by surrogate) and apart from a fail with her outfit choices during her first pregnancy, she too has had a pregnancy wardrobe that was total goals. The point I am trying to make here is that the world expected great things from Kylie Jenner when it came to maternity style, and in the beginning of her alleged pregnancy, she definitely didn’t disappoint.

Jenner posted this photo of herself on Instagram and the combination of her linen pants and a white vest is beautiful, and rather than try to disguise her figure with oversized clothing, she instead chose to place her hands strategically over her stomach.

12 She Brought Out The Pleather

Via CapitalXtra

This is the point in Kylie Jenner’s rumored pregnancy where things started to go downhill. In my opinion, I think she should have either confirmed or denied the pregnancy rumors, and if in fact she is pregnant then she should have embraced her new body and rocked clothes that highlighted her bump. Instead, what it seems Jenner has done is try to hide her figure in T-shirts.

Say hello to the pleather pants and a baggy T-shirt combo, the outfit of choice for Jenner after she passed the early days of her pregnancy. Despite the hideous tee, this outfit is still kind of cute because the pants at least give her some shape, and since it was relatively early in her pregnancy, she was able to squeeze into them without showing off every lump and bump.

11 Oversized Tees Became Her Wardrobe Staple

Via TheMirror

This is definitely one of the least flattering pictures we have ever seen of Kylie Jenner, but it does show how she starts to love T-shirts, and this seems to be because she was desperate to hide her stomach and keep the public guessing about her alleged pregnancy -- and there are only so many ways you can hide a bump.

Now, that’s not to say that she never wore a T-shirt a day in her life prior to the rumors that she could be with child because Jenner has long been a fan of comfortable and practical clothing, but this photo, which was taken in early September while Jenner was reportedly enjoying a shopping trip, did come as a bit of surprise because we have been so used to seeing her wearing tight clothes.

10 Cold Weather, Or A Clever Disguise?

Via Kylie Jenner/Instagram

Anyone who has ever owned a puffer jacket will know that they may be extremely comfortable and warm, but it’s incredibly difficult to show off your curves when wearing one of these beauties! I happen to think Kylie Jenner realized this, which is why she decided to share a half-shot of the top of her body, because in this snap there is no way any of us could have made out whether she was sporting a baby bump or not.

If this photo proves anything, it’s that Jenner’s maternity style is all about comfort (and hiding her bump), rather than body cons and other cute outfits that could potentially show it off. We have also noticed that it’s not just her style that has evolved, but also the way she starts to share photos on social media.

9 Is It A Food Baby Or A Real Baby?

Via UsWeekly

It wasn’t long into Kylie Jenner’s rumored pregnancy that we stopped seeing her flaunt her figure in bikinis and underwear, and instead noticed a dramatic change in how she shared images of herself, and more importantly of her body. But even Jenner can’t control the photos in the media of her.

This image came about when she and Travis Scott traveled to Houston, Texas in October, where, according to a Us Weekly eyewitness say they grabbed a pepperoni pizza. While on their outing, Jenner decided to wear a baggy top, this time opting for a hooded sweatshirt with embroidered roses and tight black leggings. And I actually think this is a cute look for the colder weather. The reason I say this is because it’s not as though she’s only wearing baggy clothes and her leggings create a balance between comfort and fit. Plus, this top is so cute!

8 Clever Cropping And An Edgy Leather Jacket

Via Us Weekly

Oh, Kylie Jenner, do you really think that if all your photos are cropped, and that if people cannot see your stomach they will forget the pregnancy rumors and just move on?! It may seem absurd, but it really seems as though this is Jenner’s approach to her pregnancy and all the photos that have been shared of her online in recent months have been edited to ensure there is no sign of her belly. And this also makes it extremely hard for us to determine her evolving pregnancy style.

This photo, which was taken at Kris Jenner’s Christmas Eve party at the end of 2017, is cropped at the bustline, so I can only judge the top half of Jenner’s outfit, which appears to be a leather jacket over a long sleeve dress. This is one of those maternity outfits that I wish I could see more of, because Jenner looks more put together than the other photos of her in baggy clothes.

7 Barely There Bump In Black Dress

Via TheSun

If Kylie Jenner’s pregnancy photos show us anything, it’s that she has decided to limit the colors of her wardrobe in recent months. Instead of bright, bold shades, and fabrics like lace and mesh, Jenner has toned down her outfit choices in a big way.

While photos of her from the last few months have been few and far between, those that Jenner has shared have shown that she prefers solid, neutral tones (mostly black) and that her outfits have been thick fabric or simple T-shirts. She has limited the amount of skin she shows off, presumably because she’s trying to hide the fact that she’s allegedly pregnant, and she has also been very smart about the angles she takes her photos. While you can just about make out Jenner’s stomach in this picture, it was shared on Instagram in early September so she didn’t really have much to show.

6 More Half-Photos In Baggy Clothes

Via Kylie Jenner/Instagram

I think it’s safe to say that we are all in agreeance about one thing when it comes to Kylie Jenner’s pregnancy style; she is not going for high-fashion, but rather extreme comfort. There’s nothing wrong with that, but her looks have been unexpected.

Jenner has graced the pages of many glossy fashion magazines, and she owns some of the most expensive and exquisite clothing that money can buy, so, it’s both a surprise and a bit of a style evolution to see her tone down her look and instead opt for a wardrobe that consists mostly of oversized T-shirts. Again, she chose to wear black, which appears to be her new favorite color, and again, she chose to crop the photo before any of us got a glimpse of her stomach.

5  All Black Is Especially Flattering On Pregnant Women

Via HollywoodLife

Kylie Jenner’s pregnancy style has been a hit and miss. Sure, there are some really cute outfits that she has worn over the last few months, even if they are often cropped or snapped at weird angles, and then there have been some sloppy, oversized ensembles that leave a lot to be desired. But when it comes to this photo, I feel it falls somewhere in between.

According to HollywoodLife, this image was shared by Jenner via Snapchat in early November and it shows her sporting sweatpants and a casual black sweater. Despite being incredibly plain, this look is actually quite cute, and another plus is that it’s all-black and for those who don’t already know, black is considered to be one of the most form flattering colors -- which is helpful, especially if you have something to hide.

4 Laidback Yet Stylish In A Denim Jacket

Via Kylie Jenner/Instagram

Kylie Jenner has been noticeably less active on social media in recent months and the photos that she does post of herself have been mostly selfies. There is also this one, that shows the top half of her body, but is disguised by an oversized denim jacket.

Jenner uploaded the photo on Nov. 23, 2017, and unsurprisingly, the image gave no more clues about whether she is, or isn’t pregnant. Some may argue that she looks a little bigger than normal, but oversized clothing can give the illusion of this, and the area that everyone is really focused on has again been covered up, so there is no knowing for sure. What I will say about this photo is that this jacket is a great look for Jenner. It’s casual, like much of her maternity wardrobe has been, but it’s also a much better alternative to a sweatshirt or hoodie and looks more stylish.

3 Is That Kylie In Tights And A Khaki Hoodie?!

Via Harper's Bazaar

This is one of the most controversial photos of Kylie Jenner’s pregnancy because there is some confusion as to whether it's her in the photo. This snap made its rounds in mid-January of 2018, and multiple sites reported that this was one of the first photos of Jenner’s bump. The photo was taken at CVS and if it is Jenner, then there seems to be no denying that she is, in fact, pregnant because it shows her heavier than before. And again, no surprise here but she has been trying to hide her stomach.

She opted for tight-fitting leggings, and a khaki hoodie, and paired the look with sandals -- which is relaxed, but also pretty trendy. However, according to TMZ, their sources say that although this woman resembles Jenner, it’s not her. I can’t be sure of this, so you decide!

2 The First Real Baby Bump Photo!


Kylie Jenner’s behavior in recent months has changed significantly, and as I mentioned before she has become a lot less active on social media and has hardly been seen at all in public. Of course, this is going to suggest to everyone that she has something to hide, and that that something is a baby bump. And if ever we needed proof, this picture is exactly that.

According to TMZ, this photo which was shared on Jan. 25 of 2018, is proof that Jenner has a “full-on baby bump.” She was reportedly walking on a Hidden Hills construction site, although the reason why has yet to be revealed. Also, her outfit is pretty awful. I’m all for comfort, and Jenner has been a fan of tracksuits and sweatpants before the pregnancy rumors, but her options were usually more tight-fitting and actually showed off her curves instead of trying to bury her body in clothing and hide any sort of shape.

Girl, what are you thinking?!

1 The Telling Calvin Klein Advert

Via Calvin Klein/Instagram

We haven’t seen a full-body picture of Kylie Jenner in months, and for the most part, she has decided to limit her public appearances. Odd, yes, but it could also be that she just wanted a break. So, it was not really until I saw this Calvin Klein advert that I became convinced Jenner had something to hide.

The ad includes all of the female siblings in the Kardashian/Jenner clan, and while Khloé, Kim, Kourtney, and Kendall are flaunting their figures, Kylie is hiding hers. Plus, it’s particularly odd that she’s on the end and covering her stomach with a blanket. Why is only half your figure showing, Kylie? Do you have something to hide? It’s been months, and the clues are racking up, so I really don’t know why she doesn’t just come clean!

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