“Do I look fancy?” my five-year-old daughter, Ruby, asks as she tromps through the living in her plastic high heels. Camouflaged by a layer of caked-on makeup, Ruby’s cherubic face is barely visible. She has smeared her cheeks with a gaudy red blush and her lips glisten with shiny neon pink gloss. With gobs of sparkly teal eye shadow on her lids and a sequined jump suit, she looks like a miniature harlot.

“You look fabulous!” I gush.

I am not training Ruby to compete in kiddie beauty contests; in fact, before I had kids of my own, I was disgusted by parents who let their little girls wear makeup – even for playing dress-up. Why would they teach their kids that they needed to get gussied up to look good? Society pressures kids to grow up too quickly as it is, I thought smugly. To me, makeup fell in the same category as My Bling Bling Barbies, skimpy bikinis, and “I’m a sexy bitch” t-shirts for tots. Ick.

Perhaps my attitudes about makeup were a bit extreme. Having lived at the feminist co-op at my all-women’s college, I viewed makeup as just another form of patriarchal oppression. I went years without wearing it and even now only daub on a bit for the rare date night out. I want Ruby and her big sister, Jesse (8), to feel beautiful au naturale without the help of any store-bought products.

So when my parents presented the girls with a deluxe Disney princess makeup set a couple of years ago, I was shocked at my reaction. As I watched my daughters gleefully dig through the makeup kit, indiscriminately smearing lip gloss, blush, and eye shadow all over their faces, I actually found myself smiling. Tarted up like deranged tramps the girls actually looked : cute. Maybe makeup wasn’t so bad after all.

“Look at me! I’m a movie star!” vamped Ruby as she struck a pose. “Call me Queen Alanday,” joked Jesse, who bowed down, took her little sister’s hand, and twirled her around. They pranced around the living room, which had somehow morphed into a castle. I whipped out my camera and directed an impromptu photo shoot.

Why the sudden change of heart? On the simplest level, I didn’t want to be a Scrooge and spoil their good time. But my feelings about makeup run deeper than that. As with most parenting decisions, I view the makeup issue through the prism of my own experience.

As a teenager, I had severe cystic acne that no amount of makeup could hide. I hid my face behind thick locks of curls and did my best to avoid mirrors. Experimenting with makeup was for girls who felt worthy of attention. Since I wasn’t comfortable in my own skin, I certainly didn’t want anybody to take a second look at me. Instead of accentuating the positive, I just pretended that my appearance didn’t matter.

I see now that perhaps my ideological anti-makeup stance was a just convenient way to avoid dealing with my own insecurities. Of course, it’s what’s inside that really counts, but it’s important to take pride in the outside too.

Part of the pleasure I get from watching my daughters play with makeup stems from the realization that they are clearly so comfortable with their appearances in a way that I never was. I envy the fact that they relish the prospect of dressing up in tutus and tiaras while I still wear my drab “mom uniform” (t-shirt, jeans, and sneakers) every day.

I’m also learning that a lot of what I believed in absolutely before becoming a parent is not as absolute as I thought. Isn’t being a good parent about letting your kids express themselves and occasionally following their lead?

Seeing my girls get a kick out of dressing up even inspired me to have more fun with my own appearance. Last Friday, I broke out a fitted dress that I reserve for special occasions, paired it with black pumps, and applied some lipstick, blush, and mascara – just to pick up the girls from school.

“You look beautiful, mommy!” exclaimed Ruby. “You always look beautiful, but now you look fancy.” I felt pretty fancy too.

I’m also beginning to appreciate that my daughters are trying on makeup while they are still too young to understand the larger societal implications. For them, makeup isn’t yet about attracting a guy or looking sexy; it’s about expressing themselves as girly girls and trying on different roles – mermaid, cowgirl, superhero – not to mention the magic of all that glitter!

I reason that if I banned makeup outright, it would only turn into a forbidden fruit that the girls would only crave more. Then, by the time Jesse and Ruby became teenagers, they might overdo it as a means of rebellion.

By allowing my daughters to play with makeup at home, I have begun a conversation about the topic that will hopefully continue through their teen years. Eventually, I hope to put all of my women’s studies courses to good use by teaching them about the thin line between sexual expression and exploitation. Seeing ads for Hannah Montana or Bratz dolls, I asked Jesse recently, “Do you think makeup makes you look better?” “No, it’s just fun to play with,” she said.

Ruby, meanwhile, likes to wear the new satin purple princess gown she got for her 5th birthday and set up cups and saucers for tea. “Look at me!” she screams, puckering her rosy lips.

“You look beautiful, but you know you don’t need to wear makeup to look beautiful, right?”

“I know,” she answers with a grin.

“Just checking,” I say.