The sisters got candid about Kendall Jenner's high school acne insecurity during a new YouTube video
kendall and kylie
Credit: YouTube

Kendall Jenner has always been open about her acne journey, but watching her go through the highs and lows of her skincare struggle was hard for sister Kylie Jenner.

"I knew it was your biggest insecurity and every time like clockwork we would get out of the car [at school], you would pull me into the staircase and you would say, 'How do I look today?'" Kylie, 23, recalled while wiping away tears during the sisters' "Drunk Get Ready with Me" YouTube video.

"It always made me so sad to even hear you talk about it. I'd be like, 'You're so beautiful,' trying to help. But then I had to go away by myself. It makes me feel bad. When you have your own daughter you just think about this," Kylie (who shares her 3-year-old daughter Stormi Webster with Travis Scott) added.

Kendall and Kylie; YouTube
Credit: YouTube

As the sisters did their makeup together while taking shots of Kendall's new 818 Tequila, the model, 25, revealed that she started wearing more makeup when she entered 9th grade because her breakouts were at their worst.

"I remember the summer before 9th grade is when all my acne went crazy and I was like, 'I'm going into high school and this one guy's really hot.' I'm going to ruin all my chances!" Kendall said. Adding, "I didn't! We ended up dating. It was the confidence that came from within that really probably turned him on to me."

Once school started, Kendall said she would "try" to do her makeup but she "knew nothing about [it]."

"I would have so much acne. Every morning we would show up to school. Dad would drop us off and we'd be walking up the stairs. I'd look at you and I'd be like, 'Can you see my acne?'" Kendall remembered. Kylie replied, "I know, I know."

Looking back years later, Kendall recognized that "clearly you could see my acne." She said, "It's bumps on your face." But she was thankful that Kylie boosted her confidence when it came to her skin concerns.

"Every day you would say, 'No you look beautiful.' I would be like, 'Okay.' I knew you were lying but I appreciated you," Kendall said.

Though the supermodel's Instagram feed is filled with flawless photos, Kendall has been the first to admit that it hasn't been easy to manage her acne and anxiety. "I honestly had never really spoken about [my acne] before, but a lot of people had seen me struggling with it mostly through paparazzi photos or the Golden Globes," Jenner told PEOPLE in Jan. 2019.

Now, she's got her skin under control, but said it can "always" feel "frustrating" when a pimple pops up. "One zit can really freak you out because you're like 'Oh no, are we going backwards again?'" Kendall said. "But I try not to think too deeply about it because I know it's going to be all good. I want everyone to know I'm okay, and you can be okay too."