Celebrity Style

19 Times Kendall Jenner Freed The Nipple In The Most Stylish Way

They’re some of her best looks ever, TBH.

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Kendall Jenner attends The 2022 Met Gala Celebrating "In America: An Anthology of Fashion" wearing a...
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At this point in her illustrious career, Kendall Jenner has modeled practically every article of clothing known to mankind — on runways, in campaigns, and in the pages of magazines. But during her downtime, she keeps coming back to one daring look — and it’s of the nipple-baring variety.

While Hollywood is growing more accustomed to the breast-positive look, Jenner has been a decade ahead of the risqué trend now taking over. The supermodel has been sporting the style since 2014, when she made her runway debut for Marc Jacobs’ New York Fashion Week show. In the decade since, the 818 Tequila founder has donned the nip-forward style countless times.

She’s rocked the sheer look to hang out with friends, as well as attend exclusive red carpets. Jenner even took the bold aesthetic for a spin at the most prestigious fashion event in the world, wearing a mesh-like crop top to the 2022 Met Gala with absolutely nothing underneath.

These looks aren’t just daring and chic, they also make a powerful statement. After all, nipple censorship (looking at you, Instagram) stems from harmful and sexist societal norms. There is nothing shameful or offensive about existing in your body and showing it when you want to. And Jenner drives that point home daily.

See all her best, most revealing ensembles ahead.

Beach Goddess

While others start the new year with resolutions and promises of change, Jenner starts hers with the chicest of beachside looks.

While frolicking on the sand with a wine glass in tow, the 818 Tequila founder bared nip in a frilly dress that featured a massive navel cut-out.

Lady In Red

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To attend the 2023 Academy Museum Gala, Jenner knocked it out of the in with an ultra-sophisticated cherry red number (a major 2023 hue). She styled the floor-length Fendi creation without accessories and without bra.

Leather Details

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For your next girls’ night out, take a cue from the ensemble Jenner wore to meet her friends for dinner. She merchandised an asymmetrical, sheer top with all-leather items: a pencil skirt, boots, clutch, and belt. So good.

Saucy Feathers

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This head-to-toe cobalt blue number (which also happens to be completely sheer) is the picture of decadence. The feathered skirt is just icing on the sartorial cake.

Touch Of Floral

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I’m obsessed with this thong-bearing, one-shoulder dress. The Anthurium choker offers a whimsical take on the rosette trend, Carrie Bradshaw’s favorite look.

Elegant Knits

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For fall, consider heavier knits for a more subtle and weather-appropriate approach to bra-free dressing. Ex: the reality star’s sleek pleated look.

Dramatic Textures

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At the 2022 Met Gala, the Keeping Up with the Kardashians alum wore a sheer crop top with an embroidered mesh overlay and paired it with a massive skirt from Prada. When she walked up those steps, it was a historic fashion moment.

Graphic Print

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One’s décolletage doesn’t have to be the highlight of every bra-free look. In this ensemble, focus was all on the intricate print.

Cool Casuals

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While in Paris, Jenner was spotted in a casually cool number: an uber-trendy denim maxi skirt paired with the simplest of white tanks.

Gauzy Collars

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The reality star elevated her denim cut-offs with lucite heels and a collared button-down made of perfectly gauzy fabric.

White And Easy

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A white tank is Jenner’s go-to when it comes to nip-showing ensembles. This time, she styled the staple with gray trousers, a striped sweater, and a baseball cap.

Luxe Fabrics

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There are so many A+ details within this single look: the sheer material spotted with ornate embroideries, the deep V neckline, the exposed undies, and the contrasting red lip. Ten out of 1, no notes.

Laid-Back Black

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Leave it to Jenner to look utterly effortless while walking around NYC. Her diaphanous wrap-style dress, paired with boots and a moon bag is sheer (get it?) perfection.

Shimmering Sheer

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The reality star glistened in a shimmery (totally sheer) gown with ‘80s-style shoulders and a thigh-high slit. And in glamorous gold no less.

Casual Chic

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Remember normcore? Jenner does too. She rocked the aesthetic with denim cut-offs, a white tee, a button-down, and the quintessential 2015-era shoe: Birkenstocks.

Dazzling Mesh

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Jenner looked positively radiant in a gilded mesh mini dress that sparkled with every move. It was completely translucent, fully showcasing her undies (and nips, obviously) underneath.

Red Hot

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The supermodel went pop-punk in a flimsy red turtleneck sweater and lace-up leather pants. To this day, her ‘fit goes just as hard.

Tulle Confection

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Marc Jacobs’ NYFW show in 2014 was history-making for Jenner: it was her first-ever runway show and it was the first time she rocked the revealing look in public. Little did she know it would wo

Her Modeling Debut

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Marc Jacobs’ NYFW show in 2014 was history-making for Jenner: it was her first-ever runway show and it was the first time she rocked the revealing look in public. Little did she know it would one day become her signature.

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