29 of Kourtney Kardashian's most daring looks

·14 min read
Side by side of Kourtney in a brown latex bodysuit in a black minidress with a black veil and in a cropped shirt and asymmetrical skirt.
Kourtney Kardashian has a signature minimalist style that gets edgier and more iconic every year.Pierre Suu/Getty Images; Nino/Getty Images; Taylor Hill/Getty Images
  • Kourtney Kardashian wore several daring looks for her destination wedding with Travis Barker in May.

  • Some consider her a fashion underdog among the Kardashian-Jenners, but she has a signature style.

  • Kardashian opts for blacks and neutrals, and has worn edgier pieces since dating Barker in 2021.

Kardashian wore a sparkling, figure-hugging catsuit for Sean "Diddy" Combs' birthday in 2015.

Kourtney in a black lace catsuit with a sparkling gold fabric underneath.
Kourtney Kardashian attending Sean "Diddy" Combs' birthday party on November 21, 2015.Allen Berezovsky/Getty Images

She attended Sean "Diddy" Combs' 46th birthday party in Beverly Hills in style. Kardashian wore a lace catsuit with a skin-colored fabric underneath that made it appear sheer. Gold flecks also sparkled throughout the bodysuit.

The following year, she opted for a fur coat and sheer shirt while out in New York City.

Kourtney in a beige, black, and white feather and fur cropped coat, a sheer top, and leather pants and boots.
Kourtney Kardashian walking in SoHo in New York City on February 10, 2016.Raymond Hall/Getty Images

Kardashian wore a shaggy color-blocked coat, chic leather pants, and booties fitting for New York City winter weather in February 2016. However, she also wore a sheer top with an exposed bra underneath, serving more as a style statement than an additional layer of warmth.

The following day, she stood alongside her family in coordinated Yeezy x Balmain looks.

Kris Jenner, Khloe Kardashian, Kendall Jenner, Kourtney Kardashian, Kim Kardashian, Caitlyn Jenner, Kylie Jenner, and North West dressed in white, cream, blush, and crystal ensembles.
The Kardashian-Jenner clan (Kourtney is in the middle) attending Kanye West's fashion show at Madison Square Garden on February 11, 2016.Kevin Mazur/Getty Images

The Kardashian-Jenner clan showed out and coordinated at a fashion show presentation for Kanye West's line, Yeezy. They each wore custom collaboration pieces from Yeezy and Balmain.

Kourtney Kardashian wore a crystal-and-pearl encrusted turtleneck and culotte jumpsuit. She was also styled in clear plastic heels.

Kardashian wore a leather crop top and shorts for a 2016 Las Vegas nightclub opening.

Kortney in a black leather bra crop top, high waisted shorts, over-the-knee boots, and a choker.
Kourtney Kardashian arrives at JEWEL Nightclub's opening weekend in Las Vegas on May 22, 2016.Denise Truscello/Getty Images

In a look that is typical of Ariana Grande's aesthetic today, Kardashian first wore the revealing black leather ensemble in 2016 for a Las Vegas club opening. Her August Getty Atelier bralette crop top and high-waisted shorts were complemented by over-the-knee boots and a matching choker necklace.

She made a fashion statement with a plunging neckline at the 2016 Glamour Awards.

Kourtney in a red sparkling dress with a wide plunging neckline and cutouts around her waist.
Kourtney Kardashian arrives at the Glamour Women Of The Year Awards on June 7, 2016.Mike Marsland/Getty Images

At the Glamour Women of the Year Awards in June 2016, Kardashian attended in a sparkling maroon dress by Julien Macdonald. The dramatic plunging neckline was held together by a sheer piece of mesh, and the waist and leg cutouts had sparkling beads. She paired the look with Gianvito Rossi metallic heels.

In October 2016, she wore a cutout minidress for a night out in Paris.

Kourtney in a leather plunging halter neck minidress with cutouts along her hip and thigh with lace up heels.
Kourtney Kardashian arrives at the Alaïa fashion showroom on October 2, 2016.Marc Piasecki/Getty Images

Kardashian wore a black leather Alaïa dress to the Alaïa fashion showroom in Paris, France. The plunging halter neckline and hip and thigh cutouts held together by buckles were revealing for Kardashian at that time.

Her makeup was also much harsher and angular than usual.

Her 2016 Angel Ball gown had daring cutouts with mesh panels.

Kourtney in a black strapless gown with ruffles and large cutouts along her thighs with mesh paneling.
Kourtney Kardashian attending the Angel Ball on November 21, 2016.Jamie McCarthy/Getty Images; Kevin Mazur

Kardashian attended the 2016 Angel Ball to honor her father and make a donation for cancer research. The media personality opted for a racy dress that was daring from every angle. The strapless and ruffled gown had sheer panels that exposed the sides and backs of Kardashian's legs.

At a 2017 pre-Grammys party, Kardashian wore a revealing dress with exposed corset detailing.

Kourtney in a black sheer cutout dress with spaghetti straps, a slit, and corset showing through.
Kourtney Kardashian arrives at a Pre-Grammy Gala on February 11, 2017.Steve Granitz/Getty Images

This sultry lingerie-looking dress had many daring elements. If the bikini-cut top and center leg slit wasn't enough, the sheer torso panel with exposed corseting details really made a statement.

She dazzled in a sparkling suit sans shirt at the CFDA Fashion Awards in 2018.

Kourtney in a black suit with silver sparkles throughout and no shirt underneath.
Kourtney Kardashian arrives to the CFDA Fashion Awards on June 4, 2018.James Devaney/Getty Images

With her studded suit by Christian Siriano, Kardashian wore layers of cross necklaces in place of a blouse.

Kardashian dressed up biker shorts in 2018 with surprisingly complementary pieces.

Kortney in a dark denim peplum jacket, biker shorts, and mesh heels.
Kourtney Kardashian walking in SoHo in New York City on June 5, 2018.Raymond Hall/Getty Images

Taking a page from her sisters' style books, Kardashian paired biker shorts with pieces that were far more dressed up. With a bold peplum jacket by Acler, a mini Louis Vuitton purse, and mesh mule heels, the combination seemed random, yet somehow worked.

In February 2019, she looked elegant in a sleek and sultry Versace gown for a charity event.

Kourtney in a black gown with thick straps, a neckline with a peak in the middle of her cleavage, and a high leg slit.
Kourtney Kardashian attends the amfAR New York Gala on February 6, 2019.Jared Siskin/amfAR/Getty Images

She turned up the elegance in a black Versace gown at the amfAR Gala in 2019. The chic dress featured a reverse sweetheart neckline and thigh-high slit. She paired the dress with pointed heels and a voluminous high ponytail.

The following night, she walked in New York wearing a trench coat and sheer shirt and bra.

Kourtney in a mint green trench coat, matching high-waisted trousers, and a sheer white mesh bralette.
Kourtney Kardashian out for dinner in New York on February 7, 2019.Gotham/Getty Images

Kardashian loves an exposed-bra-under-a-suit moment, and a great example is this look. Under a pale-green trench coat and tucked into matching trousers, Kardashian wore a completely sheer mesh top. And under that, her lace bra was also sheer.

Kardashian wore a vintage Vivienne Westwood corset in 2019.

Kourtney in a lace corset with a scoop neckline and one strap on one shoulder with high-waisted trousers.
Kourtney Kardashian in New York on February 7, 2019.Robert Kamau/Getty Images

The queen of corsets, Vivienne Westwood, has created stunning and intricate corsets that many would love to get their hands on — Kardashian did just that when she wore a one-shouldered structured vintage Vivienne Westwood corset in 2019.

The archived piece came from fashion dealer Johnny Valencia's Instagram account @Pechuga_Vintage. Kardashian was also styled in a pair of high-waisted trousers with tuxedo stripes along the legs.

She wore a checkered leather coat for a New York outing in 2019.

Kortney in a color-block black and white leather trench coat with a black shirt, leather pants, and dark sunglasses.
Kourtney Kardashian in New York on February 8, 2019.MediaPunch/Bauer-Griffin/Getty Images

She has a knack for wearing unique and dramatic coats whenever she's in New York City. On one outing, she stood out in a black-and-white checkered coat by Céline. She paired the color-blocked piece with a black turtleneck, leather pants, boots, and dark sunglasses.

On the same trip, she wore an edgy look with a print of the Mona Lisa on her chest.

Kourtney in a black leather trench coat and a beige catsuit with prints of Mona Lisa on it.
Kourtney Kardashian walking in Chelsea in New York City on February 8, 2019.Gotham/Getty Images

During New York Fashion Week in 2019, Kardashian stepped out in a semi-sheer catsuit with Leonardo Da Vinci's Mona Lisa painting printed over it. She wore another daring trench coat — this time by Helmut Lang — and made the look even more edgy with square sunglasses and combat boots from The Row.

Kardashian wore a signature boxy suit with an exposed bra to Diana Ross' birthday party in 2019.

Kourtney in an oversized sparkling silver blazer with matching flared trousers and a black bra underneath.
Kourtney Kardashian arriving at Diana Ross' birthday party on March 26, 2019.Hollywood To You/Star Max/Getty Images

Kardashian went to celebrate Diana Ross' 75th birthday with a bang. Her boxy blazer and flared trousers sparkled all over and were styled with a barely there black bra.

She stood out from her sisters onstage at the 2019 NBCUniversal Upfront event.

Khloe, Kourtney in a strapless yellow and cheetah print midi dress and Kendall on stage.
Khloe Kardashian, Kourtney Kardashian, and Kendall Jenner present at NBCUniversal's Upfront event on May 13, 2019.NBC U Photo Bank/Getty Images

At NBCUniversal's Upfront event in 2019, Khloé and Kourtney Kardashian and Kendall Jenner presented for their show "Keeping Up With the Kardashians."

Kourtney stood out in a bright-yellow and leopard-print strapless Alex Perry midi dress.

She wore a sparkling pink slip dress out in LA in 2019.

Kourtney in a pink sparkly slip minidress with black lace trim and lace up heels.
Kourtney Kardashian in Los Angeles on June 29, 2019.Hollywood To You/Star Max/Getty Images

Kardashian took to the streets of Los Angeles in a pink sequined slip dress with black lace trim designed by Versace. She paired it with black strappy heels.

Kardashian later included photos and a selfie of her wearing the same outfit in an Instagram post in May 2021 with the caption, "pinkalicious."

Her striped, sparkling suit dazzled at the 2019 People's Choice Awards.

Kourtney in a black and and sparkly silver striped suit with no shirt and a black bra underneath.
Kourtney Kardashian arrives to the People's Choice Awards on November 10, 2019.Amy Sussman/E! Entertainment/Getty Images

She kept with her classic boxy suit and exposed bra look at the 2019 People's Choice Awards. Wearing a Naeem Khan suit with silver pinstripes, a black bra, and slicked-back hair, Kardashian dazzled on the red carpet.

In 2020, Kardashian proved she's just as fashionable as her sister Kim in a latex bodysuit in Paris.

Kourtney in a chocolate brown latex catsuit with knee high black leather pointed boots. Kim in a similar caramel latex catsuit.
Kourtney and Kim Kardashian attended the Balenciaga Paris Fashion Week show on March 1, 2020.Pierre Suu/Getty Images

During 2020 Paris Fashion Week, Kardashian wore an amazing chocolate-brown body-hugging latex jumpsuit by Balmain. Her sister Kim wore a coordinated caramel Balmain ensemble.

Not only did she wear the shiny look to Balmain's fashion show, Kardashian wore it that day to Kanye West's church service.

She mixed browns and different textures for a chic dinner look in 2020.

Kourtney in a brown leather trench coat, beige smokey print mini dress, and over the knee slouchy caramel suede boots.
Kourtney Kardashian in Tribeca in New York City on October 10, 2020.Gotham/Getty Images

Kardashian mixed textures in an all-over-brown look while out to dinner in New York City. She wore a marble-print minidress, brown leather duster coat, and over-the-knee suede stiletto boots. At the height of COVID-19, she also wore a face mask by Kim Kardashian's brand SKIMS.

Kardashian mixed hard and soft in this 2020 look, wearing a blazer as a dress.

Kourtney in a light blue tie dye belted blazer worn as a dress with a black face mask and combat boots.
Kourtney Kardashian SoHo in New York City on October 10, 2020.Gotham/Getty Images

Kardashian wore a stunning blue and white watercolor-print blazer for a day out. Paired with black accessories and chunky combat boots, she perfectly captured New York street style.

Kardashian wore an edgy and risqué minidress on the 2021 VMAs red carpet alongside Travis Barker.

Travis next to Kourtney in a black off the shoulder leather minidress with long sleeves and a lace up neckline from her belly button.
Travis Barker and Kourtney Kardashian attending the MTV Video Music Awards on September 12, 2021.Jason Kempin/Getty Images

In the last few years, and especially since dating Travis Barker, Kardashian has shown off an edgier style. For the couple's debut red-carpet appearance, they arrived at the Video Music Awards in coordinated black looks.

Kardashian wore a leather off-the-shoulder minidress by Olivier Theyskens. It had a bustier bodice with lace-up ties from her belly button to the neckline. She paired this with a Prada purse and strappy heels.

She also wore this to present Barker's performance with Machine Gun Kelly later in the night.

Alongside Barker in 2021, Kardashian wore a punk-rock snakeskin jacket dress.

Kourtney in a dark snakeskin leather belted leather jacket worn as a dress with knee-high chunky leather black boots.
Kourtney Kardashian and Travis Barker walking in Tribeca in New York City on October 14, 2021.Gotham/Getty Images

Kardashian usually wears dark colors or rock 'n' roll-inspired pieces when she's with Barker. Here she wore a dark-green snakeskin safari jacket-like dress by Lēo. She cinched the waist with a black belt that complemented her chunky platform leather boots and sunglasses.

At the 2022 Vanity Fair Oscar Party, she wore a vintage gown with different elements and textures.

Kourtney in a beige, black, and silver gown with lace, cutouts, and straps.
Kourtney Kardashian and Travis Barker attend the 2022 Vanity Fair Oscar Party on March 27, 2022.Daniele Venturelli/Getty Images

Kardashian changed out of a black jumpsuit and into this vintage Dolce & Gabbana number for the 2022 Vanity Fair after-party alongside Barker. The color palette, sparkles, cutouts, and straps were reminiscent of a flapper dress.

Kardashian attended the Met Gala for the first time in May 2022 in an off-theme Thom Browne ensemble.

Kourtney in a white cropped long sleeve button-down collared shirt. She's wearing a skirt with light cream fitted high-waisted piece that turns into a black asymmetrical skirt with a train and white stitches.
Kourtney Kardashian and Travis Barker attending the Met Gala "In America: An Anthology of Fashion" event on May 2, 2022.Taylor Hill/Getty Images

For Kardashian's first-ever Met Gala appearance on May 2, 2022, she showed up with then-fiancé Travis Barker in coordinating Thom Browne ensembles. This was also the first time the designer created a couple's look for the event.

Kardashian wore a cut-off button down shirt and a black asymmetrical skirt with white stitching and a contrasting hip cummberbund.

"I love how I was the deconstructed version of [Travis'] perfectly polished look," Kardashian wrote on Instagram. "I had all of the elements from his look draped all over me. His pleated skirt, jacket and suit pants were dripping from my skirt."

Kardashian told her company Poosh that she had to stand up in a van to travel to the Met and "The Thom Browne team had to finish sewing up a few details on my skirt, and they literally sewed until the moment I had to step out onto the carpet."

When red carpet correspondent and TV personality La La Anthony asked how the pair interpreted the "Gilded Glamour" theme, Kardashian responded, "I honestly didn't really think about it," according to Buzzfeed.

On May 4, Vogue shared a behind-the-scenes video of the couple getting ready for the Met. In the video, they came to the conclusion that they looked like Jack Skellington and Sally from "The Nightmare Before Christmas."

Kardashian and Travis each went from one daring outfit to another later in the night after the Met.

Kourtney in a black strapless minidress with a shiny square black pattern.
Kourtney Kardashian and Travis Barker leaving a hotel in New York on May 2, 2022.Raymond Hall/Getty Images

Kardashian and Barker then changed their outfits to attend a Met Gala after party. Kardashian opted for a micro minidress, also by Thom Browne. The revealing look had an all-over shimmering houndstooth print with exposed corset detailing and boning. This paralleled her look from earlier that had exposed, contrasting stitches.

Kourtney in a burgundy-red sheer long dress revealing a red bodysuit underneath. The sheer dress has sporadic blue floral applique. She has burgundy fur wrap around her arms and red criss-cross strappy heels.

Kourtney in a burgundy-red sheer long dress revealing a red bodysuit underneath. The sheer dress has sporadic blue floral applique. She has. burgundy fur stole around her arms and red criss-cross strappy heels.
Kourtney Kardashian at Ristorante Puny in Portofino, Italy, on May 20, 2022.Nino/Getty Images

Kardashian and Barker had several wedding celebrations from an unofficial Las Vegas chapel ceremony on April 4 to their Los Angeles courthouse wedding on May 15 and an Italian destination wedding on May 22.

The Kardashian-Jenner-Barker clan arrived in Portofino, Italy, to attend the couple's multi-day wedding celebration. They were all said to be dressed by Dolce & Gabbana for each event.

On May 20, the family had dinner at Ristorante Puny. Kardashian wore a daring archival Dolce & Gabbana sheer burgundy gown from 1998, according to Daily Mail. The tulle bodycon dress with floral appliqués overlayed a spaghetti-strap bodysuit. She was also styled in a fur wrap worn off-the-shoulder and strappy heels.

 

Kourtney wearing a black sweetheart minidress with thin straps. The dress has an illustration of the Virgin Marry over her abdomen. She has on a black cropped veil with blue lace along the hem. She has black over-the-shoulder gloves and black strappy heels on.

Kourtney wearing a black sweetheart minidress with thin straps. The dress has an illustration of the Virgin Marry over her abdomen. She has on a black cropped veil with blue lace along the hem. She has black over-the-shoulder gloves and black strappy heels on.
Kourtney Kardashian arriving at the Abbey of San Fruttuoso in Portofino, Italy, on May 21, 2022.Nino/Getty Images

On May 21, the family took a boat ride around Portofino before having lunch at the Abbey of San Fruttuoso. Kardashian was dressed in a daring, goth ensemble consisting of a black Dolce & Gabbana minidress with a religious emblem of the Madonna, or The Virgin Mary, and a sheer black and blue lace-trimmed veil.

This look, which also came from the fashion house's 1998 collection, according to People, was styled with black opera gloves and strappy heels

The following day, Kardashian had her nuptials to Barker at Domenico Dolce & Stefano Gabbana's estate in a custom look: a white lace lingerie-inspired minidress with a satin corset and an intricate veil that also included a design element of the Madonna.

After their ceremony, Kardashian celebrated at her reception in a black version of her wedding dress, also by Dolce & Gabbana.

"Designing my dresses with Domenico and Stefano has been a dream come true in every way," Kardashian told Vogue on May 22.

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