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My Toddler Stylist

My Toddler Stylist

A month ago, Summer Bellessa posted a hugely popular blog post about how she let her toddler dress her for a week. Of course I thought this was a brilliant idea so I did it too, until I decided I was at risk for being known around town as the crazy mom and needed to wear something normal before the neighbors requested a welfare check on me and the kids.

I was going to post the pictures right after I took them, but then preschool registration hit. This was followed by the stomach bug, which tapered off into my birthday, so OBVIOUSLY I had better things to do, like clean other people’s puke out of my hair and argue with Tiny Boss over whether it was his birthday month or mine.

But then today my friend sent me this link, which is kind of a compilation of other moms who let their toddlers pick out their clothes for a the week. Because what better way is there to assess the level of antipathy your toddler holds for you than to give him free reign over your public appearance for a few days?

Anyways, here are my “TODDLER DRESSED ME FOR A WEEK. TODDLER HAS WRONGED ME” photos. Enjoy!

Day 1: Barefoot Running Meets Elegance

Passes for normal? Don't worry, he was just warming up.

Passes for normal? Don't worry, he was just warming up.


Although I had to draw the line at bathrobes, this wasn’t a bad ensemble, even with the Vibram Five Fingers on my feet.

Day 2: Pattern Blindness


Would you like to know how Tiny Boss chose this outfit? You can recreate this “dressed in the dark look” in just four easy steps:

1) Rummage through pants drawer and choose the first pair of pants you see that aren’t jeans or khakis.

2) Spend ONE FULL MINUTE swinging shirts around on hangers before discovering one that’s both too tight around the arms and the belly.

3) Stop to quote Anna Wintour: you either know fashion or you don’t.

4) Find a handbag that usually isn’t used because, you know, it’s kind of ugly.

As we headed out the door, I got smart. I’ll just throw a jacket over this hot mess! Problem solved.


Throw on a jacket, problem solved! Right?

“Find me a jacket,” I commanded (you can’t let them know you’re afraid, or they’ll tear you apart like a pack of wild dogs).

“This one!” he said, with a confidence I pray he keeps when he’s older. He grabbed a wool coat I used to wear to work all the time. You know, before I had kids who picked out garish outfits for blogging’s sake.

And because I’m a masochist: “Now shoes?”

A pair of neutral patent leather wedges. And off we went to breakfast on that Sunday. I did turn a few heads – “These are my church clothes!” – was what I had practiced saying in my head in case anyone said anything to me, but no one actually seemed to want to make eye contact after the initial double take.


All in all, the second day was a good experiment. I posted my outfit picture onto Facebook and received some very helpful insight, including:

1) Apparently my purse looks like both a diaper bag and also a laptop bag. Can I sell this idea on The Shark Tank?

2) Other people want to pick my clothes, too.

3) I have nice scarves.

Day 3: Well, That Escalated Quickly


This day has traumatized me so much that I just can’t even. A lot of my friends who saw the photos actually told me they liked it, but they probably are just hoping I write them in my will so that in the likely event I die of embarrassment, they get a cut.

The alternate outfit chosen for me today was this:

Since I'm breastfeeding and I have two kids, I can't be drunk. Otherwise, I might have actually considered wearing in public this Liz Lange Target nightgown.

Since I'm breastfeeding and I have two kids, I can't be drunk. Otherwise, I might have actually considered wearing in public this Liz Lange Target nightgown.

Day 4: Grin and Bear It


Some of those same supportive friends suddenly turned on me. “Why do you have those pants at all?” “The fact you’re wearing them means these were in your closet!” Talk about victim blaming.

Others insisted they liked it. I’m sure they think they do, but until I see them in a polka dot top paired with criss-cross lattice pants, I’m going to take their compliments with a grain of salt.

Day 5: Salvation


I know you won’t believe me after seeing the carnage from Days 3 and 4, but Tiny Boss picked this entire outfit! Something I would actually have picked for myself! so, Tiny Boss, maybe we’ll have to try this again after all. Like, in 15 years when whatever I’m wearing is actually embarrassing you more than me.




I used to think being an attorney was a tough job. Then I had kids.

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