Charlie Goes to School

He was ready. I am still getting there.

Charlie is starting school full time. It’s been a few months since we made the decision, and now it’s coming fast — this is our last week with our nanny, he does a transition week after Memorial Day, and he starts full time in June.

If you’ve been following along, you know we’ve had the most wonderful nanny — genuinely one of the best decisions we ever made as parents. But as Charlie gets closer to two, we found ourselves doing the math that I think a lot of families hit at this stage: nanny plus a twos program, or full-time school? It sounds like a simple calculus. It wasn’t.

We did a gentle separation program this past year — a pre-twos class twice a week, with his nanny by his side. Watching him there told us almost everything we needed to know. He lit up. He learned. He wanted to be there, with his friends, moving, doing, exploring. Charlie thrives in structure in a way that honestly surprised me. He loves other kids. He loves having a place to be.

So we made the call. And it was hard to get there, even knowing it was right. Our nanny is someone we love dearly, and saying goodbye to that chapter is genuinely bittersweet.

The school itself made the decision easier — we fell in love with it. And the thing that pushed us fully over the edge: it’s a Spanish immersion program. I started learning Spanish around two and a half when someone came to live with us and I just... absorbed it. That gift has stayed with me my whole life. The idea that Charlie gets to start that way too felt like something we couldn’t pass up.

So. Here we are. Big kid era, officially.

What We Got Him — and Why

Once I accepted that this was actually happening, I went into full logistics mode — because that is how I cope, and I’m not ashamed of it. I put together everything we bought (and actually love) in a ShopMy board called Charlie’s School Setup — also linked below. But I wanted to walk you through the things I’m especially glad we found, because some of this took more research than it should have and I’d love to save you the time.

The Eating Situation — Now in Stainless Steel

We went all-in on LALO for Charlie’s lunch setup and I have zero regrets. We were so excited when they launched their new stainless steel collection, and it felt like the perfect timing. The bento box is the right size for a toddler portion without being overwhelming, and the lil dipper snack box is genuinely genius for anything dippable — which, if your toddler is anything like mine, is everything. We paired both with the stainless toddler cup. What we love beyond the obvious: the pieces feel secure without being too hard for little two-year-old hands to open, which also aligns beautifully with the Montessori philosophy of fostering independence.

For the actual lunch bag and backpack, we went with Mark and Graham’s Riley mini backpack and insulated lunch box. I’ll be honest — I wanted something that looked good walking into school, and the matching set delivered. They’re monogrammable — and once I went down the personalization rabbit hole, I never came back. For those of you not deep in the monogram rabbit hole, the Polo Bear backpack from Ralph Lauren is another option I almost pulled the trigger on — and honestly still might.

We also added the Owala kids tumbler for water. Keeps things cold, easy to drink from, and Charlie has strong opinions about it, which means he actually uses it.

Labels, Because I Am That Mom

Turns out the personalization rabbit hole has a second level, and it’s called Name Bubbles. I put Charlie’s name on everything — the cups, the containers, the backpack, the jacket. The preschool label pack covers basically every surface and they actually stay on through the wash and the dishwasher. I did not know I would care this much about labels. I care this much about labels.

The Clothing Situation (Which Is More Specific Than You Think)

Here’s something I didn’t fully anticipate until we got the school paperwork: Montessori programs have very specific clothing requirements. Because the school takes over potty training, they ask for five extra pairs of pants or shorts, five pairs of underwear, and a few t-shirts and a light sweater — all kept at school for accidents. No pull-ups allowed. Diapers and real underwear only, which felt like a big leap but is apparently very intentional to the Montessori method.

So yes, we bought a lot of basics. Gap and H&M became my best friends.

From Gap, we stocked up on the parachute joggers, pull-on everyday joggers, quick-dry shorts, vintage soft sweat shorts, and pocket tees in a three-pack. Everything pulls on and off easily — which matters enormously when a teacher is helping eight two-year-olds in the bathroom. The no-show socks in a 7-pack were a no-brainer, and the organic cotton briefs are what we’re using for the underwear requirement. We also grabbed the mix and match pull-on joggers for extra rotation.

From H&M, the cotton piqué polo shirts, drawstring joggers, and cotton boys’ briefs round out the rotation and add a little more personality. H&M toddler clothes are genuinely underrated and I will die on this hill.

And one more thing Montessori requires that I didn’t think about until orientation: indoor shoes. Street shoes come off at the door and go straight into his cubby. We got Charlie Crocs — they slip on and off independently, which is a big Montessori value, they’re washable, and he loves them. Done.

Diapers and Wipes

We’re still in diapers — school is taking over the potty training process, and honestly? I am grateful. I have been dreading this and genuinely scared to commit to a naked weekend. Letting the school lead felt like the right call for us. We use Coterie diapers and have since the beginning — they’re the best we’ve tried, full stop. The Coterie flush wipes go everywhere with us too.

For accident clothes coming home, we got Mushie wet bags. Keeps everything contained, doesn’t leak. Essential.

Sun Protection

Charlie’s school goes outside every day — roof playtime and neighborhood walks are both part of the routine, and he’s starting in June, so sun protection is non-negotiable from day one. The Mustela mineral sunscreen stick lives in the bag permanently. SPF 50, goes on clean, no fight. And the Ralph Lauren ball cap is our other line of defense — a little bit of a splurge in the context of a toddler hat, but it’s classic, it fits well, and it completes every outfit.

This is just what we’ve got so far. But this is my first time doing this, and I am absolutely certain I will change my mind one hundred times and buy one hundred more things before we hit our stride. For those of you who have been through this — please, I am begging you, tell me what I’m missing. Drop it in the comments. I need all the advice I can get.

And while you’re down there — how do I not cry at drop off every day? Because I never thought I’d say this, but I’m going to miss him running in while I’m on Zooms.

Everything linked above is also saved in one place on my ShopMy — find the full Charlie’s School Setup board here. 🍎