Nana Zee’s Back-to-School Rituals for the Grandkids: Little Things That Make the First Day Feel Big

There is back-to-school, and then there is the very first back-to-school.

That first day of nursery school, preschool, or kindergarten is different. The backpack may be almost as big as the child wearing it. Their new shoes are still perfectly clean. They are a little scared and at the same time excited about everything that’s new to them. Hoping they see neighborhood friends, checking out their classroom, and meet their teacher. It’s all so much fun right up until the moment they realize that Mom, Dad, Nana, or Grandpa isn’t staying. I remember it well (I also remember the calls from Ben’s nursery school teacher because he wouldn’t stop crying).

Suddenly, this new adventure feels even bigger than expected.

As a Nana, I think grandparents have a particularly fun role to play in all of this. We aren’t the ones trying to get everyone dressed, fed, and out the door by 7:42 a.m. We’ve already been there, done that with our own some 30 years ago. Now we can be the people who add a little magic. We can take them shopping for a special first-day outfit. We can tuck a surprise into a lunchbox. We can give them their first “big kid” water bottle, buy the silly pencils with the characters they love, have a snack waiting after school, and while mom and dad are still at work, we can be the ones who sit down to hear every single detail about their day, even if the answer to “What did you do today?” is, “Nothing.”

But back-to-school shopping doesn’t have to be about buying everything on a supply list, especially when they are my grandson’s age (3) and heading to nursery school. Mom and dad will be doing a lot of the basics, so I went out to look for my favorite finds this year. These are the things that make school days easier, more comfortable, and a whole lot more fun.

So, from one grandparent to another, here’s Nana Zee’s Back-to-School Guide for the Grandkids, with a little extra love for those tiny students heading off for the very first time.

Start With the Lunchbox

For young children, lunch isn’t just lunch. It is one of those familiar moments in the middle of a completely unfamiliar day. They may be in a new building with new teachers, new children, and a new routine, but when they open their lunchbox and see foods they recognize, packed by someone who loves them, home suddenly doesn’t feel quite so far away.

The Ello Benni Kids Bento Box

I’m a big fan of anything that makes lunch more fun without creating more work for the grownups, which is why a kids’ bento box makes so much sense.

The Ello Benni Kids Bento Box gives you separate spaces for all of those little things kids like to eat. And let’s face it. Little kids tend to be grazers. A few berries here, crackers there, a sandwich cut into small pieces, some veggies, cheese, fruit, or whatever happens to be on that child’s current “I will actually eat this” list.

The bento approach also lets grandparents make lunch a little more special. Cut a sandwich into a heart or star. Add a tiny note. Slip in a favorite treat on Friday.

If you’re a grandparent who lives nearby, offer to pack lunch once a week. It sounds like such a small thing, but you’re helping the parents while giving your grandchild something to look forward to. FYI, they will absolutely LOVE personalizing their own lunchbox with the charms. It’s the first thing my grandson did (again and again and again). Should the taco go here or there? What about the soccer ball?

Available at Ello Products

Don’t Forget the Water

Next to the bento box, I’d add the Ello Ellies 12-Ounce Stainless Steel Kids Water Bottle. This leak-proof, 12 oz. stainless steel water bottle features adorable animal-inspired designs that keep kids hydrated from the classroom to after-school adventures. Having a water bottle that is just “theirs” is another little step toward independence. They will stop asking to use Mom’s or Dad’s, and for a child just starting school, there are suddenly a lot of things they’re learning to manage on their own. Their backpack. Their lunch. Their jacket. Their cubby. Their water bottle.

This one got an immediate squeal of WATER BOTTLE!!!! He knew exactly how to pop the top open (something that took me a minute to figure out) by simply pushing the button of a mouth to reveal a straw. All I remember hearing is…Can I use it now???

Here’s my Nana tip. Put their name on everything. Not just the backpack. Everything. Because as I recall, school classrooms contain mysterious portals through which water bottles, sweatshirts, and lunch containers disappear forever.

Available at Ello Products (look around the site; there are LOTS of fun drink and food storage products.

When They Want a Warm Lunch: Daniel Tiger to the Rescue

Some kids simply don’t want another cold sandwich, especially once the weather gets cooler. A Daniel Tiger’s Neighborhood Stainless Steel 13 oz Food Jar can turn leftovers, pasta, soup, or another favorite warm meal into their favorite school lunch. I don’t know about your grandchildren, but things like mac & cheese or leftover meatballs and macaroni are always a hit with mine.

For a child going to nursery school or kindergarten, having a familiar character like Daniel Tiger along for the day can also be comforting. That’s something I think we sometimes underestimate as adults. To us, it’s a food jar. To a four-year-old, Daniel Tiger is coming to lunch with them.

And for those first few weeks of school, I’ll take every little bit of reassurance we can give them.

Available at Amazon

For the Bigger Kids, This Lunchbox Actually Heats Lunch

For older grandchildren, college kids, teachers, and even the parents heading back to the office once summer is over, the UVI self-heating lunchbox is one of those products that made me think, “Where was this when I needed it?” UVI is a portable lunchbox that can heat refrigerated food in about 25 minutes when plugged in. It has adjustable compartments, an insulated liner designed to keep food warm for up to two hours, and an integrated UV-light sanitizing function for use after the lunchbox and utensils have been washed. The UVI Plus adds USB-C compatibility, a 34-ounce capacity, reinforced leakproof clamps, and movable dividers.

This is obviously one for older students who are permitted to use it, rather than the little ones heading into kindergarten, but I love the idea for teenagers who stay late for activities, college students, or even a grandchild starting their first job. It also makes leftovers a much more appealing lunch option and it comes in a variety of colors (because we know that they all have their favorites).

Nana made baked ziti last night? Suddenly today’s lunch looks pretty good.

Available at UVI

Because a Napkin Is Sometimes Laughably Inadequate

You know your grandchild…

Chocolate around the mouth. Jelly on the cheek. Something sticky on all ten fingers. And somehow there is something you can’t quite make out in their hair.

How? Beats me (and I’ll never get a straight answer, so I stopped asking). But this is why I’m putting Yipes! Wipes in the lunchbox and backpack.

Yipes! are face and hand wipes designed just for kids. They’re made with 99% plant-derived ingredients and 98% water, and they’re hypoallergenic and dermatologist-tested. The individually wrapped wipes are especially handy because they are really easy to open, so kids can open them themselves and you can tuck a couple into a lunchbox without sending an entire bulky package.

They’re great for after lunch, after the playground, after art class, and after whatever mysterious substance your grandchild has managed to encounter between drop-off and pickup.

A napkin is optimistic. A Yipes! wipe is planning ahead.

Available at Yipes! Wipes

The First-Day Outfit Matters More Than We Think

Do you remember getting a new outfit for school? I do. There’s something about walking into school wearing something you love that gives you just a tiny bit more confidence. For little ones, favorite characters can make that first-day outfit feel even more special.

Daniel Tiger Oversized T-Shirt

The Daniel Tiger Oversized T-Shirt from Hanna Andersson is exactly the sort of first-week-of-school piece I’d choose for a little Daniel Tiger fan. My grandson is a little smaller than a 3T, and he LOVES Daniel, so you know he’ll be wearing this one proudly. It’s playful, comfortable, and familiar. More importantly, it gives a nervous little student something they already love to take along on this brand-new adventure.

Grandparents, this is a great opportunity to start a tradition. Take your grandchild shopping for one special Nana-and-me first-day outfit every year. We love to do this online so we can cuddle up and look at all of his favorites.

Don’t forget to take a photo on the first morning. Keep them all. Someday those photographs, from the tiny preschooler swallowed up by a backpack to the teenager who suddenly towers over Nana, are going to be priceless.

FYI, these run true to size (but slightly oversized, so when cooler days come you can layer a plain long-sleeve T-shirt underneath). They remind me that when my son (his dad) was young, I’d dress him in Hanna Andersson all the time, and it brings back memories.

Available at Hanna Andersson

Daniel Tiger French Terry Set for Cooler Fall Days

When cooler mornings finally arrive, there’s also the Daniel Tiger Oversized French Terry Sweatshirt and Sweatpants Set. For young children, I’m firmly on Team Comfortable for school. In preschool and kindergarten, they’ll be sitting on rugs, climbing playground equipment, painting, building, dancing, running, and occasionally flop dramatically onto the floor because someone else got the blue crayon.

School clothes should let them be kids. But these are more than that. These are Nana, I want to get comfortable after-school clothes, can we go to the playground weekend clothes, and I just want to cuddle with you Nana Zee clothes (I like those best). The French Terry is soft and cozy, and I love that they can mix and match the top and bottom with other pieces.

Available at Hanna Andersson

Let Nana Be in Charge of the FUN School Supplies

Parents can buy the practical things. Nana gets the fun aisle.

That’s where Oriental Trading comes in. Back-to-school season doesn’t have to consist entirely of notebooks, glue sticks, and No. 2 pencils. Oriental Trading is basically permission for grandparents to get a little silly. I love Personalized Pastel Pencils because a child’s name instantly turns an ordinary pencil into their pencil. They’re fun for a pencil case, homework station, or even a first-day gift.

The Classroom Work Ketchup Folders can help make all those papers traveling between school and home feel a little more organized, yet silly at the same time. And then we get to the things no teacher technically puts on the supply list.

Those are my favorites.

There are Micro Pet Rubber Ducks, plus teacher and student rubber ducks that would make adorable little first-day surprises. Slip one into a backpack with a note wishing them a “ducky” first day, or let your grandchild bring one to a favorite teacher.

The Monster Mayhem Collection is another fun way to add personality to school supplies and celebrations, particularly for kids who prefer goofy monsters to something overly sweet. And I don’t know that anyone technically needs a stuffed balloon dog. Which is precisely why Nana should buy one.

Grandparents have earned the right to occasionally purchase something for absolutely no sensible reason other than, “This is going to make my grandchild laugh.” Luckily, Oriental Trading has everything to provide them.

You can even pick up a little something for Nana as well like a Flo the Flamingo keychain, tumbler, socks, and stickers. There is something delightfully Florida-Nana (that’s ME) about carrying a flamingo around while everyone else is heading back to school. Put the keychain on the bag you carry to pick up. Keep the tumbler in the car. Wear the socks when you’re on after-school duty.

The kids don’t get to have all the fun.

Have fun shopping at Oriental Trading

The Best Back-to-School Gift Might Be a Book

School shouldn’t be the place where reading becomes a chore. Especially with younger children, I want books to remain adventures. They should be about snuggling together, asking questions, discovering animals and places they’ve never seen, and saying, “Wait. Read that part again.”

Daniel Tiger’s Peek-a-Flap Trolley

For preschoolers and young kindergarteners, Daniel Tiger’s Trolley Peek-A-Flap book is a natural extension of the Daniel Tiger theme. The interactive board book takes young readers through the Neighborhood with Daniel and Trolley, with familiar friends including Prince Wednesday, O the Owl, and Miss Elaina. It uses sturdy lift-the-flaps to encourage kids to peek, discover, and interact with the story, which makes it particularly appealing for little hands and short attention spans.

This is the kind of book I’d keep at Nana’s house. Because part of back-to-school should be creating a routine that says reading isn’t only something we do because a teacher tells us to.

We read because it’s fun.

Available on Amazon.com

Build a Nana’s Nature Book Basket

For older children, I’d create a special after-school reading basket and add books that introduce them to wildlife, conservation, and the world beyond their classroom from the Green Kids Club. Books can open children’s eyes to a much bigger world, and Green Kids Club uses engaging stories to teach young readers about animals, conservation, and protecting the planet. The organization partners with respected conservation groups, including Elephants Without Borders, Saving the Survivors, and Blood Lions, to create children’s books inspired by real environmental challenges.

A portion of the proceeds from each collaborative book is donated to the conservation organization featured in the story. Green Kids Club also brings these lessons into classrooms through in-person and virtual experiences and works with the Love the Wild Foundation to distribute books to children around the world.

These are wonderful books for grandparents to read with their grandchildren. Along with enjoying a meaningful story together, you can start age-appropriate conversations about kindness, endangered animals, and the small things every child can do to help care for our planet. It is a thoughtful way to encourage curiosity, compassion, and a lifelong love of both reading and the natural world.

Start with White Wolves of Yellowstone.
Then add Grizzly 399.
I’d also include Lili the Brave Bee’s Flight for a New Home and A “Tail” of Three Lions.

Together, books like these allow grandparents to talk with kids about animals, habitats, and our responsibility for the world around us.

Ask questions.

“What would you do?”
“Which animal would you want to see?”
“Where should we go someday?”

That last question is dangerous if you’re a travel-loving Nana. Before you know it, you’re planning Yellowstone. But that’s part of the fun.

All four (and more) books are available at Green Kids Club

There is a particular kind of hunger that only occurs at approximately 3:15 p.m.

Children come through the door as if no one has fed them since Tuesday. This is where the Fritaire Air Fryer earns its spot in my back-to-school kitchen.

Fritaire uses a transparent tempered-glass bowl, which means you can actually watch what’s cooking. Sometimes we just stand and watch our after-school snack cook through the glass. It circulates heat around the bowl and offers nine cooking modes, including air fry, bake, dehydrate, and rotisserie, along with a tumbling basket and self-cleaning function. The glass bowl has a four-quart capacity, and the unit can preheat in under two minutes.

For grandparents doing afternoon pickup, an air fryer makes it easy to get a warm snack on the table without turning snack time into a production. Think crispy veggies, little pizzas, chicken bites, warmed leftovers, fries, or whatever your grandchild considers the greatest food ever this week. It’s fun to watch those chicken strips or fries tumble as you cook them together for the young ones. Oh and it comes in so many different colors that I’ll be you can find their favorite.

Better yet, let older grandchildren help prepare something with you. Because here’s the secret. The snack isn’t really the important part. It’s the conversation that happens while you’re making it.

Available from Fritaire

Create a First-Day-After-School Tradition

This may be my favorite idea in the entire guide. If you have the opportunity, make the first day of school something you celebrate afterward, too.

Pick them up.
Have their favorite snack waiting.
Put a ridiculous little Oriental Trading rubber duck at their place.
Ask about their teacher.
Ask who sat next to them.
Ask what made them laugh.
Ask what felt scary.
Ask what they want to do again tomorrow.

And don’t worry if they don’t tell you much. Sometimes little kids need time before the stories come spilling out. You can even make a little First Day at Nana’s box each year with a book, pencils, stickers, a tiny toy, and a treat. It doesn’t have to cost much. That’s the wonderful thing about grandparent traditions. The value has almost nothing to do with the price.

When School Is Scary, Nana Can Make It Feel Smaller

I think we forget how enormous nursery school and kindergarten can feel to a child. Imagine being three, four, or five years old and walking into a building filled with strangers, being told where to sit, when to eat, where to put your things, and when the grown-up you trust most is coming back.

That’s a lot.

So grandparents can help prepare them before the big day. Have a practice lunch at home using the new bento box and water bottle. Let them practice opening and closing everything themselves. Wear the new Daniel Tiger outfit around the house. Read the Daniel Tiger Trolley book and talk about going someplace new. Practice putting the water bottle into the backpack. Let them choose which pencils they want. Make getting ready feel exciting instead of mysterious. And perhaps most importantly, tell them that it’s okay to be excited and a little scared at the same time.

Nana’s Secret Weapon: A Tiny Lunchbox Note

You don’t have to buy anything for this one.

Take a tiny piece of paper and write:

Nana loves you. Have fun today! For those who can’t read yet, add a smiley face or a heart. Draw a terrible picture. Put on lipstick and leave a kiss.

For a child who can’t read yet, Mom or Dad can tell them what it says before putting it into the lunchbox. Pretty soon they’ll recognize that little heart or Nana’s handwriting before they can read a single word.

For older grandchildren, change the messages.

You’ve got this. Can’t wait to hear about your day. Friday = ice cream with Nana. Even teenagers who roll their eyes at you may secretly keep them. And if they don’t, that’s okay too. Keep writing them.

Back to School Is a Milestone for Grandparents, Too

There’s something bittersweet about watching a grandchild walk into school for the first time. We’re cheering because they’re growing. We’re also thinking, “Wait. Didn’t we just meet you?” The years move much too quickly. That’s why I don’t think grandparents should treat back-to-school as something that belongs only to parents and children. We get to be part of it too. Buy the personalized pencils. Help choose the lunchbox. Put Yipes! in the backpack because you already know exactly how lunch is going to end. Read Daniel Tiger one more time. Make the after-school snack. Take the first-day picture. Ask too many questions. Celebrate the tiny victories.

And when that little one walks into nursery school or kindergarten carrying a backpack that looks entirely too large for their body, remember something.

We’re not just watching them go to school. We’re watching them become themselves.

One classroom, one book, one new friend, one messy lunch, and one brave first day at a time.

And if Nana can tuck a little extra love into the lunchbox for the journey, all the better.

Happy back-to-school from Nana Zee.