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19 MOST TALKED-ABOUT KYLIE JENNER OUTFITS OF ALL TIME

Each of the five Kardashian-Jenner sisters has had their own fashion journey. Kim loves a sensual style with a sporty touch, Kourtney has moved from trendy to grungy, Khloe favors stylish activewear, and Kendall’s model-off-duty look is clean and chic. Kylie Jenner’s outfits, however, are often more surprising than her older sisters’.

From bold colors to body-hugging styles and simple French-girl looks, you never know what Kylie will wear next. We love that she keeps us guessing! While her sisters have clear styles, Jenner enjoys trying out different looks, and with so many designers available to her, it makes sense to mix things up.

Kylie Jenner’s outfits—whether on the red carpet or in everyday life—offer lots of fashion ideas for everyone. To help you keep track of the beauty mogul and mom of two’s best looks, we’ve picked out some of our favorites.

KYLIE JENNER IN L.A. IN AUGUST 2018

The Kardashian-Jenners are all about that Barbie vibe, and Kylie is definitely no exception. It’s hard to pick what we love most about this look—the stunning dress, the chic shoes, or the sleek platinum ponytail!

KYLIE JENNER AT THE MTV VMAS IN 2018

There’s no need to tell you that the business owner and founder is a boss; this sharp blazer dress outfit speaks for itself.

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2018

Why go for denim-on-denim with separates when you can nail the Canadian Tuxedo look with a stylish jumpsuit? This all-denim outfit is definitely one we can support.

KYLIE JENNER AT THE GRAMMY AWARDS IN 2019

Balmain suits Jenner perfectly, as shown by this blush pink jumpsuit with dramatic sleeves she wore to the Grammys. We imagine this one-piece is as comfy as it is beautiful; it’s a nice change from her usual body-hugging dresses, and we love it!

KYLIE JENNER AT THE MET GALA IN 2019

At one point, Jenner had a purple phase. She brought back her signature color for the 2019 Met Gala and perfectly captured the “Camp: Notes on Fashion” theme.

SOPHISTICATED SEXY

For the premiere of Travis Scott: Look Mom I Can Fly, Jenner chose an outfit that exuded sophistication. The white bodycon dress highlighted her signature curves, while the sexy back cutouts added a fun twist. We also loved the addition of the bow choker!

KYLIE JENNER AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2021

This mermaid-style gown from Ralph and Russo combines sparkly fun with Old Hollywood glamour. Jenner said the look was worth it, even though it made sitting down a bit tricky!

KYLIE JENNER IN L.A. IN MARCH 2021

Is it just a coincidence that Jenner wore a strikingly similar outfit to celebrate the Haqq sisters’ birthday in 2023, just like she did in 2021 at the same venue? The only difference is the color: red instead of black. It just goes to show that even celebrities repeat outfits—sort of!

KYLIE JENNER AT THE BALMAIN SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Having designer friends definitely pays off, especially when they create exclusive looks just for you. Jenner has been a muse for many designers, but this crochet minidress by Balmain’s Olivier Rousteing is one of our top five favorites.

KYLIE JENNER IN PARIS IN SEPTEMBER 2022

Jenner is a strong supporter of the underwear-as-outerwear trend. She paired white hipster briefs with a matching tank top, black tights that blend into her boots, and a grey overcoat on top—simple yet absolutely showstopping!

KYLIE JENNER AT THE THE BOF 500 GALA IN PARIS IN 2022

Jenner is no stranger to a mesh look, but this outfit from the Business of Fashion 500 gala in Paris last fall really caught our eye. Custom-made for her by Casey Cadwallader, the creative director of Mugler, it features a stunning design of asymmetrical lace.

KYLIE JENNER AT THE COPERNI SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Although Jenner has recently been seen in more neutral tones, she’s always been “a big fan of color,” as Lizzie McGuire’s Miranda Sanchez would say. She particularly shines in blue, making the floral minidress she wore front row at the Coperni Spring/Summer 2023 show a must-have on this list. Don’t miss the matching sunglasses and heels!

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2022

Jenner has certainly influenced many street style trends, but we think she may have borrowed the no-pants look from her big sister Kendall. Regardless, she nails the leggy style with a neutral base, an oversized black trench coat, and pointed-toe heels.

KYLIE JENNER IN ARCHIVE MUGLER AT THE MUGLER COUTURISSIME OPENING IN N.Y.C. IN 2022

At the Mugler Couturissime exhibition opening, Jenner called herself the “Mugler king” on Instagram. Given that it’s been almost a year since the event and we’re still talking about her look, we definitely agree! The Morticia Addams-inspired corset dress is fabulous on its own, but her headpiece would have turned heads even without it.

KYLIE JENNER IN PARIS IN FEBRUARY 2023

Remember when Jenner experimented with bright pastel hair colors? Well, blue is still her go-to! For an afternoon stroll in Paris, the mom of two wore a long-sleeved, body-hugging midi dress in a striking blue shade, pairing it with glittering Barbie-pink boots.

KYLIE JENNER IN L.A. IN MARCH 2023

It’s no surprise that for Malika and Khadijah Haqq’s 40th birthday, the youngest Jenner celebrated in style. The Kylie Cosmetics founder dazzled in a sexy set featuring a satin miniskirt and a matching black satin peek-a-boo mesh top. She completed the look with a leather trench coat, sheer black tights, and pointed-toe heels.

KYLIE JENNER IN MAISON MARGIELA AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2023

Maison Margiela custom-made Jenner’s stunning metallic gown for the 2023 Vanity Fair Oscar Party, and the design did not disappoint. The original piece featured a statement bow tied at the bust and a cape train flowing from her mid-back. The only way this look could have been better is if the beauty mogul arrived in the Batmobile, because it’s definitely giving “superhero, but make it fashion.”

KYLIE JENNER IN JEAN PAUL GAULTIER AT THE MET GALA IN 2023

If anyone knows how to make a statement on the red carpet, it’s Kylie. The Haider Ackermann for Jean Paul Gaultier gown she wore to the 2023 Met Gala turned heads with every step. With its asymmetrical neckline, cold shoulder, and high thigh slit, this fiery ensemble was undoubtedly one of her best looks.

KYLIE JENNER IN PARIS IN MAY 2023

Jenner made a splash in the quiet luxury trend while in Paris. The reality star wore a crisp white midi dress with a corset waist and matching heels, keeping her accessories simple with small silver hoops, black sunglasses, and a tiny white handbag.

CONCLUSION

Kylie Jenner’s impact on the fashion world is undeniable. Her bold, daring, and often trendsetting outfits have captivated audiences worldwide, cementing her status as a style icon. From her early days as a reality TV star to her current role as a successful businesswoman and influencer, Jenner’s fashion choices have continued to evolve and inspire.

The outfits featured in this list represent just a glimpse of Jenner’s extensive style repertoire. Her ability to seamlessly blend high fashion with streetwear, her willingness to experiment with bold trends, and her knack for creating iconic looks have solidified her place in fashion history. As Jenner’s career continues to flourish, it is clear that her influence on the fashion industry will only grow stronger.

FASHION FAILS SO BIZARRE YOU’LL DO A DOUBLE TAKE

Fashion, at its core, is a form of self-expression and creativity, but sometimes it takes unexpected turns that defy conventional norms. Today, we’ll explore how these outlandish choices contribute to the fashion landscape, offering both entertainment and insight into the evolving nature of style.

THAT AWKWARD MOMENT WHEN YOU SWORE YOUR SHIRT SAID CANADA

Ah yes, a seemingly wholesome photo at first glance. Just a group of friends posing together, proudly wearing shirts to represent their home country of Canada. Naturally, they had to capture the moment. But when they looked back at the pictures, they realized something had gone hilariously wrong. Did you catch it? Turns out, the girl in the middle is repping something quite different from Canada!

BEACH BY DAY, RODEO BY NIGHT

Now, if these aren’t the most unique shoes you’ve ever seen, what could be? Sometimes even cowboys need a break from their trusty old boots and crave something a little different. Enter: cowboot sandals! Perfect for those hot, sunny days at the beach or lake when you want to stay true to your Western roots, but also let your feet breathe. Practical? Maybe not. But unforgettable? Absolutely!

THE DESIGNER WAS SURELY FIRED AFTER THIS

Are they sweatpants, a sweatshirt, or… sweat shorts? These might just be the most baffling shorts known to mankind. If you’ve ever thought, “You know what my shorts need? Extra sleeves hanging awkwardly by my hips,” then congratulations—your dream bottoms have arrived! Whoever designed these was certainly thinking outside the box. But the real question remains: what kind of person would actually buy and wear these?

WHEN YOU NEED TO TIE YOUR HAIR BACK BUT FORGOT A SCRUNCHIE

You know that awkward moment when you’re desperate to tie your hair back into a ponytail but realize you’ve forgotten your hairband? What are you supposed to do? Well, this resourceful girl came up with a bizarre solution. Sporting a denim jacket with rips in the back, she had the brilliant idea to thread her hair through the slits, creating an impromptu ponytail to keep it out of her way!

Well, would you look at that? While cartoons often show people slipping on bananas, now you can wear sandals that look just like one! Designed by the talented artist Gab Bois, these banana-inspired sandals are perfect for summer. Known for her unique fashion pieces and creative illusions using unconventional materials, Gab Bois has truly outdone herself with this design. If you ever get the chance to wear these, you’d better go bananas!

ANY WOMAN’S WORST NIGHTMARE DRESS

The placement of a red flower near the bottom of this woman’s white dress was definitely a questionable design choice. It took a moment to realize that it was, in fact, part of the dress. Unfortunately, at first glance, it looks like an unfortunate accident. You might wonder if she spilled something or if it’s that time of the month. The last thing anyone wants when wearing a new dress is for people to mistake a design for a stain!

SOMEONE PLEASE CALL THE FASHION POLICE NOW

Stop everything and take a good look at this photo—it’s an image you won’t want to forget. First off, how on earth does this guy even manage to get these pants-shoes or shoes-pants on? And when it comes to going to the bathroom, what’s the deal with the belt? Surely the pants are tight enough from all the laces. This is the most confusing yet oddly intriguing clothing item ever.

JUST IN CASE YOU DIDN’T UNDERSTAND WHAT WAS DUE IN THE FIRST PLACE

Being pregnant is an exciting time, and it’s natural to want to show it off. However, this shirt raises some questions. Was it designed for the pregnant woman wearing it or for someone else? Either way, whether you’re sporting a shirt of yourself pregnant or one featuring another pregnant person, it’s definitely a bit strange. 

THIS GUY MIGHT BE A TAD SELF-OBSESSED

Well, that’s definitely a look! First off, this outfit takes a lot of confidence and a strong sense of self-love. It’s pretty striking—and a bit frightening. With sequins, sunglasses, and a shirt featuring a picture of himself, it’s both hilarious and bold. Props to this guy for going the extra mile to create a shirt with his own face on it. It’s definitely an outfit for the books!

THAT’S A THOUGHTFULLY PLACED FLOWER

This lady was excited to show off her new floral dress, but something felt… off. The placement of one particular flower was questionable—right on her bum! This design is a fashion fail on so many levels. How unfortunate! How can she wear this dress without people thinking it’s meant to be something else entirely? At the very least, it’s sure to give people a good laugh. Hopefully, she’s got a great sense of humor!

WHEN THE DRESS CODE SAID PANTS BUT IT’S HOT OUTSIDE

You’ve heard of ripped jeans, worn-in jeans, mom jeans, and bleached jeans, but have you ever come across legless jeans? What’s the point of wearing these, exactly? If you had to come up with one, perhaps they’re perfect for those sweltering days when it’s just too hot for pants. But, for some inexplicable reason, you’re still in the mood to wear the skeleton of a pair of jeans. Practical? Not quite. Statement-making? 

GOODBYE WINTER, HELLO SPRING

This woman is absolutely iconic! Sporting what looks like a jumpsuit or coat along with a matching purse, all covered in daisies, she’s truly embodying springtime. Her confidence in this bold and unique outfit is something you can only admire. It’s a daring choice, but it’s so distinctive that you can’t help but be captivated. She’s definitely nailed the seasonal look!

SO THAT’S WHERE WALDO IS

Just like in a game of Where’s Waldo?, this woman’s pants have a hidden surprise! She thought she was buying Christmas-inspired leggings, but ended up with a little surprise: right between her legs is a tiny hand reaching out for something! It’s definitely a unique design choice. What’s the purpose of that hand placement? That’s anyone’s guess!

WHEN YOU HAVE A PARTY AT 10 BUT ALSO GOT MAULED BY A BEAR AT 9

If the point of a jacket is to keep you warm on a chilly day, this one seems to miss the mark entirely. With a chunk of material missing, it’s more likely to give her cold shoulders than keep her warm. Denim jackets are supposed to be stylish, but this one’s missing piece makes it look off, as if she got attacked on her way to a party and her jacket was torn apart, yet she didn’t let it stop her.

BAD FASHION OR BAD TIMING

This young girl was thrilled to graduate high school and start her first year of college. She bought a shirt to celebrate and take a photo, but no one told her that it had a spelling error. While she’ll surely figure out how to spell “college” correctly soon, for now, she could always claim her new favorite hobby is “collaging” to make the shirt seem intentional.

WHEN YOU’RE SO EXCITED FOR MOVIE NIGHT, YOU FORGET TO GET DRESSED

When desperation strikes and the craving for a good movie hits, you’ve got to do whatever it takes. In this case, that meant not wasting a single moment getting dressed. This woman, in true cinematic devotion, wrapped a sheet around herself and rushed out to rent a DVD. Her dedication is undeniable, even if her fashion choice raises a few eyebrows. But hey, when the movie calls, there’s no time for wardrobe changes!

JUST WHEN SHE THOUGHT SHE HAD THE PERFECT PHOTO

Everyone wants to be an influencer or Instagram model these days. So when this girl posed for a picture, she thought it was going to be stunning. She was in position, and the outfit seemed perfect—or so she thought. It wasn’t until she was about to post on social media that she realized what had gone wrong. Hopefully, she has a good sense of humor; otherwise, her photos might end up being more comical than she intended.

TRY A SHIRT AS A SKIRT INSTEAD

There’s a reason this piece of clothing is called a top—it’s meant to be worn on the upper part of your body! This girl might have been trying to be different and creative with her clothes, but it’s definitely a fashion fail. The vision was there, but the execution missed the mark. What’s next? Pants as shirts or underwear as hats? Sometimes it’s best to stick with clothing for their intended body part!

WHEN YOU’RE CRAVING A CUDDLE

Feeling a bit down and craving a hug or some good old-fashioned cuddling? This might just be the perfect puffer coat for you. It definitely takes a double take to understand what’s going on, but once you do, it’s both disturbing and cool. This could have been the ultimate jacket during the pandemic when everyone was feeling extra lonely and in need of some extra comfort.

WELL THAT LOOKS LIKE AN UNCOMFORTABLE WEDGIE

At first glance, it might look like this guy is walking around with a deep atomic wedgie. However, it turns out that’s actually the intended design of his t-shirt. Can you believe it? Maybe he didn’t even realize how it appeared from the back. Someone must have mentioned it to him—right? Perhaps it wouldn’t be so jarring if he just untucked the shirt from his pants.

WHEN YOU’RE RUNNING OUT OF OUTFIT IDEAS

Times are certainly changing with this new look. Moschino designer Jeremy Scott unveiled a runway show inspired by trash, and this iconic piece takes it to the next level. It’s like wearing the plastic bag from the dry cleaners—complete with a hanger on your head! And you won’t believe the price tag. Fashion truly has gone from practical to avant-garde!

SOMEONE COULD’VE WARNED HER THE SIZES WERE WAY OFF

This is a classic case of online shopping expectations versus reality. Waiting for weeks for your package, only to receive something completely different from what you ordered, can be super disappointing. The side-by-side images show the same outfit, but the sizes were clearly off. This girl thought she was ordering her size, only to receive an outfit that’s way too small. The difference is stark, and the letdown is real!

CONCLUSION

In conclusion, fashion choices that are so comical they require a double take often showcase a blend of creativity, boldness, and sometimes a touch of the absurd. These choices can range from unintentional design flaws to daring, avant-garde statements. Whether they result in a humorous mishap or a memorable fashion moment, they all reflect the ever-evolving and eclectic nature of fashion. Ultimately, such choices remind us that style is not just about following trends but also about expressing individuality, even if it means occasionally making a fashion faux pas that makes everyone look twice.