21 Times Kendall Jenner Freed the Nipple in the Name of Fashion — See Photos

“Best nips in town.” — Khloé Kardashian, 2024

Kendall Jenner is never afraid to go super, super sheer in her wardrobe, and she’s the first to ditch a bra in favor of freeing the nipple. Over the years, it’s become somewhat of a signature look for the model and reality star. If she’s dressing up for an event, you can bet she’s probably going to wear something sheer or low-cut. There’s a reason why sister Khloé Kardashian proclaimed Jenner had the “best nips in town” on Instagram.

As a model, you have to be flexible, and Jenner learned this firsthand after wearing a super sheer, nipple-baring top on the Marc Jacobs runway in 2014 — very early in her modeling career. However, she brushed it off like NBD. “I don’t know why I wasn’t nervous about that. I was really excited about my tits being out, actually,” she told W at the time. “I’m weird, I love my tits being out. It’s like one of my things, I guess.” The model wasn’t afraid of showing off her body — she embraced it. “I’m young! When I’m older, I want to be able to look at it and be like, ‘I looked good!'”

Since then, Jenner has worn countless peekaboo looks, and her attitude about showing off what we’ve been told to hide continues to be refreshing… and even a little punk rock. In 2016, she wrote about how she was firmly team #FreetheNipple on her app. (Remember when the Kardashian-Jenners each had an app? Simpler times.) “Lately, it’s like I’m either braless or I have my bra out,” she wrote. “I’m all about freeing the nipple … I just think it’s cool to show off what’s under your shirt — whether that’s a cute bralette or just skin.”

The now-iconic Marc Jacobs runway moment set the tone for an entire decade of nipple-centric looks. “I was pretty chill, even though my boobies were out,” Jenner told Vogue during her installment of its Life in Looks series. Clearly, that attitude has stuck around for the past decade, and we’re all about it.

Below, take a trip down memory lane and revisit 21 times Kendall Jenner freed the nipple — on the runway, the red carpet, and IRL.

RANDY BROOKE
1/21

Marc Jacobs, February 2014

Jenner’s first-ever public nipple-baring moment happened on the Marc Jacobs runway during Fashion Week in 2014 and set the tone for many, many more sheer, peekaboo moments to come.

MARC PIASECKI
2/21

Paris, January 2017

OK, so it’s not quite a full “free the nipple” moment, but this street style pic from a trip to Paris in 2017 is playfully punk.

HOLLYWOOD TO YOU/STAR MAX
3/21

New York City, April 2017

Jenner’s drawn-on nipples T-shirt from Never Fully Dressed was a cheeky nod to her always-braless status. She styled it with very 2017 high-waisted leather leggings, a sheer cardigan, and lime green pumps.

GOTHAM
4/21

New York City, July 2017

The model frequently goes braless during her off-time, as exemplified by this street style moment from 2017. The sheer red top and jeans combo is *chef’s kiss* perfection.

YANN COATSALIOU/GETTY IMAGES
5/21

Cannes Film Festival, May 2018

While attending the Cannes Film Festival in 2018, Jenner wore a few nipple-baring looks, including this barely-there, sparkling green Alexandre Vauthier minidress.

GEORGE PIMENTEL
6/21

Cannes Film Festival, May 2018

On the red carpet at the film fest, Jenner donned a romantic, ethereal white tulle gown with a plunging neckline and tiered skirt.

JAMIE MCCARTHY/GETTY IMAGES
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New York City, May 2018

Sweet and sheer. Jenner looked like springtime personified at a Tiffany & Co. event in a subtly see-through white minidress from Elie Saab.

MARC PIASECKI
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Paris, September 2018

For a Longchamp 70th Anniversary Celebration in Paris, Jenner opted for a sheer black gown with a dramatic, plunging V-neck over a high-waisted brief. Look closely — that’s not black lace, but horses! Perfect for noted horse girl Kendall Jenner.

SAMIR HUSSEIN
9/21

Fashion Awards, December 2018

This glimmering gold gown played peekaboo in both the front and the back; the sequins shimmered in the light and gave glimpses of Jenner’s skin underneath. So glamorous.

GOTHAM
10/21

New York City, April 2021

A white tank with no bra is a cornerstone of Jenner’s wardrobe and a key piece in so many of her street style looks. So many layering options, and a perfect match for her casual, day-off outfits.

GOTHAM
11/21

New York City, October 2021

This fitted, patterned mesh maxi dress with minimal, strappy sandals was ultra-sleek and chic — and just see-through enough, of course.

DIMITRIOS KAMBOURIS/GETTY IMAGES
12/21

Met Gala, May 2022

At the 2022 Met Gala, Jenner brought the drama in a Prada gown with a sheer top and a massive full, ruffled ballgown skirt. The top was layered over a fishnet cami for extra texture.

JEREMY MOELLER/GETTY IMAGES
13/21

New York Fashion Week, September 2022

During NYFW, Jenner went for quiet luxury with a twist in an elegant pale gray Khaite maxi dress — and no bra, obviously.

JC OLIVERA
14/21

LACMA Art+Film Gala, November 2022

OK, so this gala gown wasn’t quite nipple-baring, but the fully sheer bodice did leave Jenner’s “tits out,” as she cheekily described her style preferences back in 2016.

MEGA
15/21

Los Angeles, January 2023

In early 2023, Jenner stepped out in Los Angeles wearing a sheer, one-shoulder black dress that exposed her chest and her underwear, styling it with a very on-trend floral choker and messy ’90s Pam Anderson updo.

GOTHAM
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New York City, April 2023 

For dinner with friends (including boyfriend Bad Bunny), Jenner slipped into a dark brown mesh top from Paloma Wool with a shearling miniskirt (yes, that’s a thing) and matching boots.

GOTHAM
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New York City, April 2023

We don’t typically see Jenner in bright, vivid colors like this; she tends to stick to more subdued shades. However, she *did* stick to her go-to sheer fabric, slipping into a cobalt blue mesh dress with a feathered hem.

COURTESY OF KENDALL JENNER/INSTAGRAM @KENDALLJENNER
18/21

On a Boat, May 2023

Va-va VOOM! Jenner almost freed the nipple on a boat in a sleek black David Koma  minidress with cheeky red floral pasties that matched her red scarf.

KEVIN WINTER
19/21

Academy Museum Gala, December 2023

Jenner joined her pal Hailey Bieber on the red carpet in a bright red Fendi gown with a thick obi-style belt and a slightly sheer top.

COURTESY OF KENDALL JENNER/INSTAGRAM @KENDALLJENNER
20/21

New Years Eve, 2023

Jenner rang in the new year in classic Kendall fashion: on the beach in a gorgeous ivory gown by Helsa with a peekaboo nipple detail. She styled it with bare feet and a carefree, optimistic attitude — exactly the energy we want for 2024.

COURTESY OF KENDALL JENNER/INSTAGRAM @KENDALLJENNER
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Mallorca, June 2024

While on vacation with Kylie Jenner in Mallorca, Spain, Kendall Jenner freed the nip once again in a sheer cascading dress that made Khloé Kardashian comment: “I love when you show the Nips. Best nips in town.” Well, enough said.