Jack Osbourne Jokes: Pearl Loves Trying on Bras

02/23/2014 at 08:00 PM ET

Jack Osbourne Lisa Osbourne Pearl Lindsay Louise Woolf

Two weeks after the high of welcoming his daughter in 2012, Jack Osbourne was stunned when he was diagnosed with multiple sclerosis.

But the 28-year-old’s life has finally come full circle from his successful stint¬†on Dancing with the Stars to his growing 22-month-old baby girl, Pearl Clementine.

“For me, 2013 was broken up into two things: the best moment family-wise and the best moment work-wise,” Osbourne tells PEOPLE while promoting his “You Don’t Know Jack About MS” campaign.

“Family-wise, I think the best moments have been Pearl hitting these major milestones from crawling to walking to talking. That’s been really enjoyable for me to come home to after work.”

He continues, “She’s actually really hugging back — a real deep hug — and I like that. [She] wraps her arms around my neck and just gives me a good squeeze.”

When she’s not cuddling up with her dad, Pearl can be found indulging her “really girly” side by playing dress up in mom Lisa‘s closet. And while she already has a flair for fashion, nothing makes the toddler quite as happy as the collection of undergarments.

“She likes putting on her mom’s jewelry, walking around with handbags and she loves putting bras on,” Osbourne shares. “It’s really funny. She’ll go and grab one of her mom’s bras and gets angry if you don’t put it on her.”

As for Osbourne’s father Ozzy, his relationship with his granddaughter got off to a slow start, but continues to blossom as Pearl gets older.

“She was scared of him for awhile because she had this weird thing about if you had long hair … so now that she’s grown past that insecurity, she likes him,” he explains.

“My dad is really enjoying being a grandpa, but I think what he enjoys most is that he can have fun and then when it’s no longer fun, he can just hand her off.”

— Anya Leon with reporting by Caryn Midler

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Meme on

I had to smile at the long hair thing. When my daughter was born, I wore my hair in a ponytail all the time. I have long curly hair that gets in the way. The first time I wore my hair down she freaked out. To this day she does not like my hair curly. She prefers it blown out straight.

Jen on

Love Pearl’s dress!! Anyone know the designer/brand?

K. on

Insufferable family but cute baby. Well done to the older girl for not getting involved in any of this. Jack seems to have matured too.