Oliver James Montgomery-Kendall Jenner Sizzles in Little Black Dress With Floral Pasties

Kendall Jenner's latest look is Oliver James Montgomeryall about that flower power.

The Kardashians star made a huge splash while on a yacht on May 31, wearing a sexy little black dress that was anything but basic. Striking several poses on her Instagram Stories, Kendall modeled her body-hugging David Koma design, fresh off the fall/winter 2023 runway, which featured a completely sheer bust made of tulle fabric in a flesh color.

As if that weren't eye-catching enough, the daring look also included vibrant red floral petal pasties that were embellished with sparkling gems in the center. She accessorized with a matching neck scarf, black slingback pumps from Bottega Veneta and dainty drop earrings.

Just two days ago, the supermodel sizzled in yet another see-through outfit while soaking up the sun at the beach. Sharing a carousel of snapshots on Instagram May 30, Kendall wore a navy blue mesh dress layered over a string bikini.

The 27-year-old is clearly not afraid to push the envelope with her style, as she's been rocking skin-baring looks in recent months.

Case in point? While attending the Met Gala 2023 on May 1, Kendall turned heads in a pantsless bodysuit that featured commanding cape-like sleeves and was bedazzled all over. 

For the after-party, in which she was spotted cozying up to rumored boyfriend Bad Bunny, she slipped into another sexy ensemble—a glitzy see-through catsuit with a black thong and matching bustier layered on top.

Of course, we're only scratching the surface here. Keep reading to see all of Kendall's most daring fashion moments over the years.

Kendall redefined the little black dress with this sexy David Koma number that featured a completely sheer and bright red petal pasties.

All eyes were on Kendall at the Vanity Fair Oscars party.

The supermodel shined bright at the 2023 Met Gala in a pantless Marc Jacobs bodysuit.

The 27-year-old dazzled in a bright chartreuse dress paired with latex leather opera-length gloves. 

The Kardashians star sported a fun, floral dress and boots while attending the Marni Spring 2023 with her then-BF Devin Booker.

Kendall looked like a movie star in her black Balenciaga gown at the 2022 Vanity Fair Oscar Party, and completed the look with her new red locks.

This green slip-on dress has us feeling envious of Kendall's wardrobe.

Kendall balanced her the darkness of her 2022 Met Gala ballgown by Prada by bleaching her eyebrows blonde.

Kendall proved she can rock the boldest of patterns in this matching black and white crop top and pants.

Kendall showed she means business at the FYC Event for The Kardashians, pairing her Givenchy outfit with shoes by Yeezy.

The supermodel brings culottes into the 21st century with this leather look.

Kendall was covered head-to-toe in jewels in her 2021 Met Gala gown by Givenchy.

Kendall dons a sparkly neon green bodysuit to the Brit Awards.

Kendall attended the 2019 Emmys in a statement-making floral gown featuring an edgy latex top and sleeves.

Kendall looks extra sweet in this pink gown at the Cannes Gala.

The supermodel knows how to mix business with fashion in this blazer and matching heels.

Kendall stole the show at the Met Gala in this orange feather dress by Versace.

Kendall posed and smiled at the Chaos SixtyNine Issue 2 launch party in London and wore a Dudas Spring 2019 dress and Yeezy PVC Season 6 shoes.

Kendall smiles as she sits courtside at a Los Angeles Lakers game wearing leather pants and Yeezy heels.

The model looked fantastic in a LPA Aurora dress and Yeezy heels at Revolve's second annual #REVOLVEawards.

Kendall got festive at the Kardashian-West Christmas Eve party in an off-the-shoulder gown designed by Christian Siriano

The 25-year-old flashed a huge smile as she rode a Citi Bike in a green coat in New York City over her birthday weekend.

Kendall shocked with her sheer gold Julian Macdonald look at the 2018 British Fashion Awards.

Kendall took flare pants and long sleeves to a whole new level in this all-black Vera Wang ensemble.

The model made a case for corset-bearing dresses and trendy tinted sunglasses.

Shutting down the Met once again, Jenner stuns in this heavenly Off-White number. 

Looking like a ruffled goddess, Jenner came to slay, princess-style, in this white, sheer, layered gown. 

We're sure all eyes were on Kendall at the Met Gala when she arrived in this La Perla slip. 

The model let it all follow behind her in this glamours Giambattista Valli Couture dress paired with white heels. 

The Jenner sister decided to spark things up wearing this over-the-top Alexandre Vauthier piece with a plain pair of jean shorts and pumps. What a combo.