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.

K3ND4LL J3NN3R’S N!PPL3S ARE L3G3ND4RY – “I love my tits being out, it’s my thing!” 😱💥🔥

Khloé called them “best nips in town” – and Kendall’s been freeing th0se perky twins ever since. From the Marc Jacobs runway (2014) to Cannes in a sparkly see-through dress, she’s made b00bs her signature accessory. Her motto? “I’m young – when I’m older, I want to look back and say ‘I looked good!'” Mission accomplished, girl. 👀🔥
👇 Click to see 21 times Kendall’s n!ppl3s stole the show – and why she never wears a bra 👇
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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.

Richard Madden reveals the real struggle behind Cinderella — “The prince can’t have any… anatomy” 😳👑

Turns out being a Disney prince isn’t all fairy tales and glass slippers.

While fans saw a charming, flawless Prince Charming on screen, Richard Madden says behind the scenes was… a completely different story. 😅

The unexpected problem Disney wanted to “fix”

During an appearance on Jimmy Kimmel Live!, Madden revealed that the production had one very specific concern:

👉 his silhouette in those tight royal trousers.

According to him, Disney was determined to make sure nothing distracting showed through the costume.

And yes — that meant serious wardrobe testing.

“We had to try on a lot of jockstraps…”

Madden didn’t sugarcoat it.

He explained that he went through multiple fittings over several days, trying different undergarments just to get the “right” look on camera.

“We had about two days of screen tests… just to make sure we can’t see anything.”

Not exactly the glamorous side of Hollywood people imagine. 😬

Not just actresses — actors struggle with costumes too

Madden also pointed out something people rarely talk about:

while actresses often deal with tight corsets and restrictive dresses in period films, male actors have their own uncomfortable battles.

And in this case?

It was all about concealment rather than shaping.

Still felt exposed anyway

Even after all that effort, Madden admitted in an interview with Attitude that he still felt uncomfortable in the final costume.

The tailored outfit might have looked perfect on screen…

…but for him, it felt far more revealing than audiences realized.

The illusion of “perfect” on-screen royalty

It’s a reminder that what looks effortless in films like Cinderella is often the result of very controlled, very deliberate styling choices.

From corsets to custom tailoring to… well, very strategic undergarments 👀

👉 Movie magic is real — just not always comfortable.

Fans reaction: surprised but amused

When the story resurfaced, fans were equal parts shocked and entertained.

Because let’s be honest:

no one watches a Disney fairy tale expecting to hear about costume struggles like this. 😂

In the end, Madden delivered the polished prince audiences loved — but now we know the reality behind that “effortless” royal look was anything but simple.

#RichardMadden #Cinderella #Disney #BehindTheScenes #HollywoodStories