As a writer, once-a-singer, stage actress, on camera personality, former dancer, wannabe stylist, amateur baker and mom, I deeply believe the ability for kids to creatively express themselves is perhaps the most important skill we can help them develop. But no, I do not let my daughters wear whatever they want to school.
I've seen the quotes in celebrity magazines, about how this or that famous mom encourages her children to "be themselves" by giving them carte blanche when it comes to wardrobe choices. "I just let them be ... them. It doesn't matter if they have 14 articles of clothing on at one time. Let them just be." (You've seen these quotes too?)
I understand the philosophy behind it, but I always question: What's going to happen when someone (or some situation) calls that child out for being dressed inappropriately for the classroom? What happens when that child gets in trouble for breaking dress code guidelines in a place of business later in life because they were never raised with the conscious awareness that some things are not appropriate for certain places?
There are rules and dress codes for a reason. We should respectfully follow them in the name of raising our kids—for safety purposes and because it teaches how to respect rules and authority.
I don't care how smart and beautiful it makes you feel, find a way to be smart and beautiful without wearing the princess gown to school. Period.
Yeah, I come from that old school mentality. Quick! Someone send me back to 1955! (Maybe blame my point of view on the fact that I was raised by a mom who was a teacher.) But encouraging self-expression is one thing (that I believe in!), while learning how to successfully "be yourself" from the inside out—and still stay within certain guidelines that respect and support a school, organization, business or circumstance—is a life skill.
Learning to be yourself at school should not be dependent on wearing a crown on your head or getting dressed up as an alligator (but such costumes might make you a distraction for others, thus making the teacher's job that much more difficult). I also believe that, if you give a kid full authority without question or guidance, that same kid might not develop the ability to be themselves without involving gowns and costumes.
Our responsibility as parents spans encouraging self-expression to respectfully adhering to rules that involve appropriateness vs. inappropriateness. No, I'm not insinuating we all conform, but I am suggesting the pendulum has swung a bit too far in the name of individuality. Of course I let my daughters pile on crazy outfits and give them the freedom to experiment with creativity at home, but there is a point when individuality can turn disrespectful toward the community we live in, the school we attend or the organization we're a part of when we blatantly ignore rules on account of us wanting to "be ourselves."
Have I taken my toddlers to the grocery store in princess outfits? Of course I have (find a mom who hasn't caved to that in the name of replenishing bread and milk). But no princess dress is allowed at preschool because it's against the safety rules and is also inappropriate. I don't care how smart and beautiful it makes you feel, find a way to be smart and beautiful without wearing the princess gown to school. Period.
Case in point: Although I feel sexy in my made-for-TV-appearances dresses, I'd never wear that same dress to church ... because it's not appropriate. And, without launching into a conversation about feminism, gender biased sexism or equal rights for women, it's my job to teach my girls how to make discerning choices like these because this is the reality we live in NOW.
How many times have I had morning scuffles about inappropriate clothing with my girls? More than I care to think about. (Is 5 the new 15?) It'd be a lot easier if I just gave in, but it wouldn't be the right thing to do. So I will continue to repeat my most famous morning quote when duty calls:
"You can't wear that to school. It's not safe. It's not appropriate. Please go change now." Even if I have to repeat this 10 times.