Photos of Kylie Jenner’s Most Fashionable Braless Moments Over the Years

Like her famous sisters, Kim, Kourtney and Khloé Kardashian, Kylie Jenner is a big fan of going braless. Whether the former Keeping Up With the Kardashians personality is attending a red carpet event or running errands in Los Angeles, Kylie is totally comfortable not wearing a bra.

However, some fans have suggested the appearance of Kylie’s breasts are the result of plastic surgery. Over the years, the makeup mogul has denied getting a boob job on a number of occasions. Instead, Kylie suggested that her bigger breasts are a combination of weight gain and wearing a push-up bra. Moreover, Kylie once said that her chest always appears larger when she has her period.

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“While weight gain can increase breast size, it is the firmness and the position of her breasts that lead me to believe she has had surgical enhancement,” board-certified plastic surgeon Dr. Manish Shah, who has never personally treated Kylie, previously told Life & Style.

“Photos of her in bathing suits show that her current breasts appear to be approximately a D cup. In photos of her in a tank top even without a bra, they stand up on their own which is normally not possible with breasts of this size without implants,” Dr. Shah continued. “If you look at pictures of Kylie at 18, an age when young women are fully developed, her breasts appear to be a small B cup.”

Aside from plastic surgery, she opened up in February 2018 about how giving birth to daughter Stormi Webster, whom she shares with boyfriend Travis Scott, changed her body.

“My boobs are definitely three times the size which bothers me, I have stretch marks on my boobs, my stomach isn’t the same, my waist isn’t the same, my butt’s bigger, my thighs are bigger,” the California native said in a July 2018 YouTube video. “I really want to gain my core back, I feel like I have fake abs right now, it’s just like genetics, but I want real abs. I know I can have a super fit body — and just for my health. I want to do this, and I want to feel good.”

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By the time she gave birth to her and Travis’ second child in February 2022, the Kylie Cosmetics mogul wanted to regain her trim body shape yet was in “no rush” to do so, an insider told Life & Style that month.

“She’ll hit the gym when she feels ready,” the source added. “She lost the baby weight pretty easily with Stormi, and isn’t freaking out about it.”

Kylie eventually lost 60 pounds after her son’s birth following a lot of time spent in the gym.

“I just want to say to my postpartum moms that postpartum has not been easy, it’s very hard. This experience for me personally has been a little harder than with my daughter,” the Hulu personality admitted in a March 2022 series of Instagram stories.

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“I didn’t want to just get back to life without saying that, because I think we can look on the Internet — and for other moms going through it right now — we can go on the Internet and it might look a lot easier for other people and, like, the pressure on us, but it hasn’t been easy for me either,” she confessed before concluding with an encouraging message.

“I didn’t even think I’d make it to this workout today, but I’m here and I’m feeling better, so you’ve got this,” Kylie added.

Scroll through the gallery below to see photos of Kylie Jenner not rocking a bra while out and about.