Zen and the Art of Fashion Compromise with a Tween

I have to be honest here. My tween son has no sense of style. Zippo. Zilch. Nada.

The problem is, he thinks he does.

Left to his own devices, Boy Wonder would wear tattered camouflage pants pulled up to his chest with mismatched socks and a pilly striped t-shirt every day. I know this because we fight over this “uniform” on the regular. He’s a sentimental kid and despite the fact that certain well-loved items in his wardrobe have seen better days, he insists on wearing old and ill-fitting articles because they’re comfortable and familiar.

Either he doesn’t care that he looks ridiculous or he doesn’t think he does. Either way, I won’t have him looking like nobody owns him.

I’m all for my kid expressing himself through clothing if I thought for a minute that was what he was trying to do. For my son, it comes down to laziness. He’s got better things to do than fuss with his clothes. I can almost guarantee that he reaches into his dresser each day and puts on the first shirt and pants he grabs before ever actually opening his eyes.

When it comes to reaching a fashion compromise with my tween, I’ve learned 5 valuable lessons:

1. Comfort rules: My son will not wear anything that is uncomfortable. That adorable wool cardigan on sale that would look just perfect for holiday photos? Forget it. Cotton, cotton, and more cotton. Soft t-shirts, jeans with a hint of stretch, no annoying collars.

2. Give him a say: As much as I want to choose everything he wears, that’s not really fair. He has to wear the clothes, not me. I allow him to pick out as many pieces as he’s willing (before he gets fed up and bored) and I fill in the rest of the missing staples. I go for simple t-shirts and dark wash jeans in styles he likes so there’s no argument.

3. Final approval: It’s cool that my son breaks “fashion rules” (for whatever that means), so long as his clothes are in good shape and fit properly. I reserve the right to veto any outfit before he walks out the door if it’s just too out there.

4. Accessories: Many a fashion battle has been fought and compromised by way accessories. Yes, even with a boy. I’ll trade you those awful pants for this cool hat. Change your shirt and you can wear this belt – and so on. Most of the time it works.

5. Don’t purchase anything if-y: If my kid isn’t into an article of clothing at the store, he won’t learn to love it at home. In fact, he’ll never wear it. I’d rather not fight battles at home over clothes purchased and never worn.

In the end, we all know that clothes don’t really make the man, but they sure do help. With a little fashion compromise, my son looks as though he has style (and no one has to know his mom helped him get there).

How do you reach fashion compromise with your kids?

A big thanks to Target for sponsoring this campaign. Click here to see more of the discussion.

Article Posted 3 years Ago
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