Polka-Dots, Stripes and Glitter Everywhere: How I Learned to Let My Daughter Dress Herself

April 8, 2015 Stories

by Kimberly Haydn

Until April 11, 2015: Follow us on Instagram and join our “Best Self-Dressed” Giveaway!

At my core, I am a perfectionist. More accurately, I compulsively control every aspect of my life to the best of my ability, and have moderate panic attacks whenever things don’t go as I’d envisioned. Imagine my angst when I learned that when it comes to parenting, the most important job I would ever embark upon, life would be littered with good intentions, epic Pinterest fails, and moments where the world seemed to spin out of control faster than you can say “don’t smear that poo on the wall.”

I quickly learned that striving for perfection when it comes to parenting is about as attainable as becoming Kate Middelton’s BFF and getting to regularly raid her closet. While I transitioned fairly uneventfully into a life of uncertainty and loose planning that may or may not pan out, the one area that I fought hardest to maintain control of was my daughter’s wardrobe.

As far as I’m concerned, the moment you become a mom, your level of style can be measured by your children. Let’s face it, looking fierce sometimes falls to the wayside when you have children, but if they look stylish and put together, no one will notice that you’re wearing yoga pants and are sporting a fabulously messy bun to hide the fact that you haven’t washed your hair in days.

When my daughter was a baby, she was always decked out in designer duds, often with an adorable matching headband. Strangers at Target ooh’ed and aah’ed. Friends raided her closet at the end of each season like brides at a Vera Wang sample sale.

The toddler years were effortless. Tulle and I were bff’s. My little fashionista was always in the cutest outfits, and I never dreamed that she would show up to a play date in something that didn’t coordinate. Polka dot leggings with a striped shirt? Get out of town!

Even Halloween was a fashionable fiesta. While other little girls were dressing as Ariel or Dora, my girl was Audrey Hepburn ala Breakfast at Tiffany’s. She won a prize for that, just sayin’.

Then one day, my sweet girl decided she wanted to dress herself. What fun! Only, she loved mixing patterns in the worst way. She wore unmatched socks. She wore a brown headband with a black dress donned with silver sequins. She began reaching for shirts with puppies wearing sunglasses plastered on the front in that plastic material that cracks when you wash it a few times. Oh, the horror!

I couldn’t understand it! Hadn’t I instilled an ounce of style in the three years she’d been rockin’ her fashion game? Had she not been paying any attention when we went shopping?! Most importantly, how on earth was I going to redirect her away from the movie star puppies and back to Ralph Lauren?

The first few months were rough. I opted for tantrums over ridiculous outfits.

I squashed that little girl’s creative expression like it was a spider hiding in my shower.

Not intentionally, of course. In fact, empowering my daughter to maintain her own identity and express her feelings has always been super important to me.

One day, in the middle of a battle of wills while getting ready for a birthday party, I realized the magnitude of my actions. By forcing my idea of what looked presentable on my daughter, I was ultimately saying “what you like is wrong, and it is not ok to be yourself.”


I began to loosen the reigns, resulting in some downright embarrassing ensembles.

Like these puppy leggings that Grandma bought because I downright refused. That’s what Grandma’s are for, after-all.


Anne Klien has an amazing attitude when it comes to clothes. “Clothes aren’t going to change the world, the women who wear them will.”

Right on. While I still make subtle suggestions when it comes to my now 9 year old’s wardrobe, I realize that empowering her to rock that tragically mismatched outfit with confidence and grace is her right. Taking her out for a filet while she’s wearing her My Little Pony fleece pajama pants won’t kill anyone. If she would rather sport a handbag shaped like a duck than a Coach clutch, that’s exactly what she should do.

In fact, her favorite purse is one we bought at Goodwill, that she painted to create her own statement piece. I’m so proud of her for knowing so well what she likes and what she wants, and for not being afraid to be different. In fact, her “this is me and I don’t care what anyone thinks” spirit is one I am often envious of.


If you find yourself in a battle of epic proportions every morning while getting your little one ready for school, I beg of you, throw your hands up in the air and relinquish control to your kids.

Not only will your mornings be much less stressful, you will be empowering your children to believe that what they want to present to the world, no matter what it is, is a-ok.

You’ll be encouraging them to think for themselves, and make decisions with ease. That skill will be important in a few years when they become more and more independent by the day, and will have to make choices without your help.

If you’re ready to take the leap and allow your children’s personalities to shine through, here are a few tips for making it a positive experience while using a few ninja-like techniques to still have a little bit of control:
  • Set a few rules. Weather appropriate apparel is important, since no one likes frostbitten piggy toes.
  • Make shopping a solo event. I buy most of my daughter’s clothes on my own. Not only does it make shopping a relaxing experience, but it allows me to buy things that I think are acceptable, so that she has approved choices hanging in her closet. That being said, I do keep her in mind, and make sure to buy some things that make me want to vomit, because I know she’ll love them. I also am open to returning things that she doesn’t like.
  • For young kids, give them two or three outfits to choose from. Too many choices can overwhelm young ones, so pick a few outfits you would be happy to have them wear and let them choose which they would rather put on.
  • Promise to always listen to their feelings. Sometimes, kids have to wear something special. Maybe Grandma got them an Easter dress, or you’re having professional pictures taken and your child really doesn’t have a say in their outfit. If they say something is uncomfortable, find an alternative. If they know you’ll listen to their needs and value their input, they’ll be a lot more willing to try things on and wear what you want once in a while.

Remember, our children are individuals. They are human beings with their own ideas, tastes, and feelings.
So, don’t feel embarrassed when your mini me wants to go into the world looking like what you would consider to be a hot freakin’ mess. The confidence you instill will last much longer than the sideways glances from strangers will.

Until April 11, 2015: Follow us on Instagram and join our “Best Self-Dressed” Giveaway!


Kim Hadyn

Kim Haydn is a business and branding strategist that focuses on helping women follow their passions and find balance between running their businesses, and living their lives! She is the mother to a kind hearted 9 year old, and can’t live without vanilla chai lattes, cherry Chap Stick, or morning snuggles. Follow her on Facebook, Pinterest, and Instagram.