4 Rules for Letting Your Child Dress Herself

When your kid is ready to dress herself, be prepared to play fashion police.  
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few years of my daughter Molly's life, I treated her as my personal dress-up doll, so it was a shock when she suddenly started expressing strong opinions about style when she was 5. Her new insistence on choosing her clothes (miniskirts every day) was often adorable but also frustrating on mornings when I was running late and my little fashionista had a meltdown because she didn't like her snow boots anymore.

I soon realized that this form of self-expression was just a normal part of Molly growing up. "Kids this age can't—and shouldn't—make decisions about their school or bedtime, but they can choose what outfit they want to wear, as long as it's within reason," says Susan Engel, Ph.D., a child-development expert at Williams College, in Williamstown, Massachusetts. Since there's often a fine line between encouraging your child's creativity and letting her go to her aunt's wedding in flip-flops and a crop top, this is how to strike the right balance.

1. Understand his choices.
Children, like adults, use style to create an image they want to present to the world. For many kids, choosing what to wear helps them define where they fit into the social order at school, says Robin Goldstein, Ph.D., author of The Parenting Bible. "They're looking around and seeing what the other kids are wearing. Having the same light-up sneakers or zip-up hoodie is one way for him to connect with his peer group." Instead of choosing clothing that suits your taste, let him be part of the shopping process, Dr. Goldstein suggests. "When you're at the store ask, 'Do you like this jacket?' before making a purchase."

2. Create some standards.
If your kid wants to wear a plaid shirt with flower-print pants, she probably won't be the only one in her class flouting the rules of fashion. Insisting that she wear the dress you picked out is probably not worth the morning struggle, says Dr. Goldstein. However, you should enforce two rules: The outfit must be appropriate for the weather, and appropriate for her age. You can also explain that certain occasions have dress-up exceptions that everyone, including mommies, must follow. To foster wise outfit selections, you might sort her clothes in different drawers or bins, with labels such as "school," "play," and "dressy," suggests Dr. Goldstein. Then let her choose whatever she wants from the proper bin. If that still doesn't speed up the morning routine, it's best to select two outfits the night before and let her pick her favorite.

3. Respect the comfort zone.
Many kids aren't worried about looking good—they just want to wear clothes that feel good. "As you get older, you may be willing to put up with a stiff fabric or an annoying tag if you think a particular shirt is cool," Dr. Engel says. "But at 5 or 6, most kids don't care about anything other than their own comfort." Take the necessary steps to inspect for poking labels, harsh zippers, or scratching pockets before you offer your child a new item to try on. Then have him approve the feel before you cut off the store tags. If you find a pair of pants or a sweatshirt that your child decides to live in, buy it in a few colors.

4. Let it go.
When your child comes to breakfast and proudly says, "Look, Mommy, stripes with stripes—I match!" let her bask in the satisfaction of having put together her amazing outfit all by herself. "It's no big deal for kids to make some fashion missteps," says Dr. Engel, who points out that her own son wore orange sweatpants with a tiger tail to school every day for a year and lived to tell the tale. "If your child wears a wacky outfit and someone teases her about it, that's an important learning moment," she adds. "Does she want to change to fit in or learn to be happy in her own distinctive style?" 

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