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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.
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