Bruce Jenner: 'The Worst Days of My Life Are the Days I Have to Get My Hair Cut'

Jenner also went into details of the plastic surgery procedures he's had as he prepares to fully transition from male to female

Bruce Jenner in DVF dress

Update: In June 2015, Caitlyn Jenner came out as a transgender woman. This content was written in May 2015 before Jenner publicly announced her full transition.

Bruce Jenner hasn’t yet shown the world how her dresses “her” – his name for his female identity – but the Olympian shared a bit of his fashion sense Sunday night.

“What’s your casual style like? Is it like denim on denim,” Kourtney Kardashian asked on the first part of Keeping up with the Kardashians: About Bruce.

“I love good old jeans and a nice sweater,” Jenner, 65, replied, smiling.

The reality star also went into new detail about the plastic surgeries he’s had and plans to undergo: a nose job, an upper lip lift and work on his forehead.

“Guys have a little ridge here,” he explained in the sit-down meeting with daughters Kylie and Kendall Jenner and the Kardashian sisters.

But Khloé Kardashian was upset the women were just learning the extent and immediacy of Jenner’s physical transformation.

“There are very premeditated operations, these are not anything you decide on a whim,” she told the cameras.

In a voiceover, Kardashian said she researched the transition process online and learned Jenner would have needed to consult a doctor and psychologist.

“If that’s true,” she said, “You’ve been doing these therapy sessions for how long?”

RELATED VIDEO: Kendall Jenner On Dad Bruce: ‘I’ve Never Seen Him Happier’

Later, Jenner became emotional when asked if he’s ever worn a wig.

“The worst days of my life are the days I have to get my hair cut,” he said.

Before they knew Jenner wanted to transition from male to female, his children teased him about his long ponytail.

“I want my hair to be longer, but society says I’ve got to cut my hair because I’m a guy,” he said, adding of short hair, “Does it look better on Bruce? Yes. But it doesn’t look better on my soul.”

Keeping Up with the Kardashians: About Bruce continues Monday at 9 p.m. ET on E!

Editor’s note: Per Bruce Jenner’s request, PEOPLE will continue to use male pronouns until otherwise instructed.

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