On Sunday I announced it was his turn to pick out “church clothes.” Apparently, this phrase means nothing to a toddler. (Duh.)

Y’all, he can handle my Monday through Saturday “go pick out your clothes” directive. So Sunday should be a cinch, too, right?

Especially because I organize his drawers to foster independence. Where the important things, like polo shirts and underwear (he goes through SO MUCH UNDERWEAR), are within reach. And his closet is full of button-down shirts that he can easily reach, yank off the hanger and pull over his head – because I keep the bottom three buttons buttoned.

Jesus loves tie-dye

Then he walked out of his room wearing a tie-dye t-shirt. And I prayed to Dear Baby Jesus for the secret to dressing little boys for church. Without completely destroying their spirits.

Now we go to one of those love everybody, open and affirming churches. So tie-dye is basically the official church color. Only, it’s not what I had in mind.

I was thinking, you know, nice(ish) slacks, nice(ish) button-down shirt. I mean, how had he not noticed that I dress him that way EVERY Sunday?

Didn’t his sweet little brain notice the pattern?

Um, the only calendar-related pattern he’s picked up on at this point is “trash-truck Tuesday.”

Sunday falls into the category of one of those days when we don’t go to school. As Saturday is the other one and it’s anything-goes-clothes on Saturday, I can see how he might not have picked up on the we-wear-nice-things-on-Sunday vibe.

Well, I’d opened the door to the tie-dyed apparel. What to do now? (And honestly, no one at church cares what he wears. Gone are the days where my mom made me wear black patent leather shoes and a bonnet to church on Easter. It’s hello, jeans these days.)

I’d already dressed little brother in a frilly Southern frock. (The days are numbered for the froo-froo, male pettifor look, too.) Next to him, big brother looked like he was sporting pajamas.

The beauty of the sweater vest

I found my secret weapon in his closet: a SWEATER VEST. With a SAILBOAT. What could be classier? What little boy could resist this? And I donned my best happy, chirpy, singsong voice to extol its virtues.

It was like a pincer movement. He didn’t know what hit him. Suddenly, he was ready for the runway: church rainbow tie-dye mascot meets Cape Cod.

The boy loves a boat. Gotta use it to my advantage.

And next Sunday, I’ll lay some ground rules: whatever you want, as long as a COLLAR is involved. This could go so very, very wrong…

For more ideas on how to dress your kiddo, check out this post with 10 tips.

What are your secrets to fostering independence? Comment below or share your toddler tips on Facebook at MothersRest.