“What are you wearing?”

I ask my children this question way too often.

From hairstyles to mismatched outfits — or wearing hooded sweatshirts on 90-degree days — most of the time I’m left questioning their need for glasses while I scratch my head and whisper prayers of intervention.

It would be wonderful if they were born with impeccable taste and a great desire to keep their teeth brushed and their hair nice and styled. I might be on top of fashion trends and coordinating colors, but they’re just now learning styles they like — and if those styles actually look good or are modest enough to wear in public. They’re also still developing those important hygienic skills. So every day is a battlefield.

Tween fashion is a new world of parenting I’m only just becoming familiar with. We alternate from coaxing our tweens out of styles that hide everything about them — including their faces — to inappropriate pieces they haven’t realized show off their newly developed figures. The tricky part is knowing when to jump in and offer my opinion and when to zip my lips.

Even when I do step in and lend a helping hand to my fashion-impaired kiddos, I’m finding my opinion is less and less received the older they get. I try to ask as many questions in a neutral tone as possible to lead them in the right direction.

“Are you comfortable in that?” “Have you checked out a mirror lately?” “Does that match?”

But even then, confrontation can easily arise.

We’ve set hard rules in our house for what is appropriate, which makes denying an outfit simple enough. But the harder conversations are when something simply doesn’t match or flatter. I love that my middle school girls are developing their own fashion identity and are having fun picking out pieces that they feel represents them well. But that doesn’t mean I can’t jump in every once in a while with a tip or trick for looking their best.

And for me, I’ve had to come to terms with the fact that not every day of their lives needs to be lived to their best ability. There are certain places and things we go to where they can dress down and be comfortable — as long as they also have the ability to dress up and nicely when it matters.

Dressing well is a valuable life skill every adult needs to be able to master. But it’s not a skill we’re born with. So I’m crossing my fingers that my kiddos and I can work through the awkward preteen phase and come out on the other side well-dressed.

Rachel Higginson is a married mom to five kids. She is a New York Times and USA Today bestselling author who has received a Utopia Award for Best Contemporary Romance and Penned Con Award for Best Novella Series. She lives in Omaha.

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