Rihanna was "not allowed to wear make-up" until she was aged 16, so she would watch her mother, Monica Braithwaite, apply products in the mirror.
The 31-year-old R&B superstar - who has her own Fenty Beauty brand - was "obsessed" with watching her mother, Monica Braithwaite, apply her cosmetics when she was younger but she was never allowed to try them for herself.
She said: "My mum pretty much worked in the beauty and perfume industry for a long time - she did make-up for people and was a make-up artist - so I always loved that.
"I was not allowed to wear make-up for a very long time. But I would watch her in the mirror doing her makeup, obsessed."
The 'Work' hitmaker recalled the first time she was allowed to create a full beauty look on her face for her school pageant.
She added: "She let me wear lipstick if I was a flower girl in a wedding or something like that, but the first time I really, really did my make-up - and she did it for me - was at my school pageant. [I was] 16, just before I left Barbados."
And Rihanna remembers the first time she put on foundation "the most" because her skin looked "perfect".
She told Interview magazine: "The foundation is the thing I remember the most, because I had never seen my skin look that perfect. And it was like, 'Wow, I want to wear foundation every day.'
"My brother hated me for that. He was like, 'What are you doing? You've got to wear that every day now?' In my school, you weren't allowed to do much at all. If your hoop wasn't hugging your ear, you couldn't wear it. It was studs or a hoop that hugged your ear."