From Sportswear to Almost Sport Coats

"Yes, buddy - they are as comfortable as I can find them. And at 9 p.m. you can lose the bow tie," I assured our seven-year old, who was throwing a pre-pubescent tantrum over having to dress for wedding.

If your boys are anything like mine (and perhaps some girls too!), their closet is full of Under Armour , Nike and Adidas with hardly a hint of denim or chino in sight. And forget anything with buttons, tags or a touch of structure or polish. Which  makes dressing for things like school pictures, programs, fancier dinners or weddings a challenge.

Learning from my past mistakes, I started the hunt a bit earlier, particularly since the holidays had passed and nicer clothes were all on sale. The big one could be conned into a button down and nicer pants with hardly a fight, where the bow tie would take some major convincing. But hey, it was easier than bringing up the word "layering" or "putting product in your hair."

The little one is sensitive to clothing (buttons, zippers, tags, anything that sags - you name it), so this one called for bribery on top of thoughtful purchases of his top and bottom. And the shoes? Forget it. There's only one particular pair of New Balance in his life.

Here's where we landed:

Big one: comfortable bow tie from Dillards with a no-iron white shirt and chinos from Gap. Couple that with a pair of new Converse and he was set. We didn't require a belt or nicer socks. Verdict: he felt mostly comfortable, shirt was out halfway through and the bowtie made it almost thought he entire evening. Success.

Little one: we'd been working the shirt angle for nearly a month, pulling it out of the closet and bribing away, letting him feel the buttons and choose how he'd wear the sleeves. Surprisingly enough it went right on sans undershirt and wasn't a problem the entire night. The pants were an awesome find: UnderArmour toddler golf pants from Dillards. He didn't even notice they weren't his regular basketball pants as they were super soft and easy to slide around in. Adjustable with a forgiving button, these were amazing. And with a shirt over the top of it, they looked almost identical to dress pants. The toddler Converse were a challenge, but the width, two velcro and color worked great once he got over the stress of it. Success.

Mom borrowed a dress from her boss that was classic and comfortable for carrying 35 pounds around on the dance floor, while Daddy splurged on a new tie and pocket square. Also success.

If your boys are anywhere as tricky to go from sportswear to sport coat, here's some tips to try:

1. Start talking about it early: people like to know what's expected of them. For the anxious ones, assure them others will be dressed the same, so their spiffiness will not be noticed.
2. Use bribes: late bed time, extra books, more time with friends or a sucker.
3. Choose your battles: build you foundation around what they must wear - a nicer shirt and pants - vs. going full hog on adding the belt, coat, slick shoes, etc.
4. Try a spiffier version of their usual: if your kiddo lives in tennis shoes, try just a new pair or doing Converse. If it's basketball pants they live in, choose a fancier sport pant that looks more presentable, but feels just as comfortable.
5. As the party loosens up, so can the clothing: during the reception, near the end of a dinner, let that shirt untuck and the bow tie come off. They'll have more fun and feel more like themselves. By then the women have ditched their heels and men their coats anyway.
6. Invest less or borrow: it won't be often your boy will have to dress this way and by the next round, he'll probably have outgrown it. Shop the sales or borrow from his friends for the event. And if he wears the same button down to every "fancy" event, so be it.
7. Sing their praises: after the event, let them know how much you appreciate them looking nice and ask them how they felt in the clothes. Just because it's expected, doesn't always make it easy for kiddos who have "thoughts" on clothes.

Even better, try to "recover" with a jammie day the next day. They'll thank you.

Then, hang those clothes up they look so adorable in and think to yourself, "I deserve a glass of wine," and slip into your own version of comfy pants. It will be all kinds of happiness.