
This year we decided it would be beneficial for Sophie to participate in a school setting for a few hours a week. Since I’m a stay-at-home mom, we don’t need all-day childcare, but my husband and I agreed that Sophie would benefit from many aspects of a school-like environment (especially from a socialization standpoint since she was born during the COVID-19 pandemic). This would also give me a more structured schedule to plan my time for things like running errands, going to doctor / dental appointments, etc. so it’s a great situation for our whole family!
Additionally, I had NO IDEA (and even typing it out now I feel so clueless for not knowing) that apparently you have to start taking school tours and registering for fall admission in like January / February!! It felt a little bit like a rat race for us at the beginning of February when we started casually searching for preschools thinking we had plenty of time to peruse our options (Montessori, private, international / multilingual, public, etc.) and come to find out we basically had a week and a half to figure it out before registration closed!
We ended up choosing to enroll Sophie in a nearby location that offers half days of preschool. There are so many options to choose from, but this seemed to be the best fit for our family! Do your research (both online via reviews in addition to getting intel from other local parents) and take school tours before making a decision.
If you’re newbies to this whole preschool thing as well, I wanted to share this helpful guide regarding questions to ask on a preschool tour since this is our first foray into the education system for our children and didn’t really know where to start! My husband and I are really excited about Sophie’s preschool program and we feel confident about our decision, but getting her enrolled was a a bit of a scramble for us!
Sophie’s school provided us with a basic student supply list and I thought I’d share what items we chose (and why!), some tips to help Sophie (and us 😭) to adjust to this new chapter, and a few little ways to make the transition exciting and fun for her (especially now that she has a new little sister to share mom and dad with)!

GEAR
BACKPACK
I chose this one because of the faux leather material — I figured that it would make it easy to wipe off / clean. I also thought that this was a cute backpack personalization idea.
LUNCHBOX
Insulated bento box inside with an easy open/close water bottle (that locks to prevent leaks!).
SPARE SET OF CLOTHES
Accidents and spills happen so having an extra set of clothes (and a pair of shoes!) on hand at school is really helpful. We plan to leave this zipper pouch with her change of clothes at school in Sophie’s cubby just in case she needs them. Don’t forget to include a wet bag for teachers to put any soiled items in.
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CLOTHING
OUTFITS
I’ve seen so many parents recommending to dress your littles in clothes that are potty-friendly (read: no jumpsuits / overalls, button flys, etc.) and are easy to pull down and get re-dressed independently.
My favorite place to shop for our girls’ clothing staples: Children’s Place — they also have great options for those littles going to schools that require uniforms! I’ve also been surprised to see school uniform style clothing at Target and Gap / Old Navy?
I’ve also heard that it’s super helpful for your little one to know how to put jacket / coat on alone so that the teacher doesn’t have to help ~15 small children get dressed to go outside.
SHOES
Shoes with Velcro make it possible for kiddos (and teachers!) can get them on / off easily. If your little one has a tough time determining which shoe goes on which foot, maybe these clever insole shoe stickers will be helpful for them?
NAME LABELS
As I’m certain you’re aware, kiddos are super prone to misplacing things, especially items that aren’t worn all day (such as hats, gloves, jackets, etc.) so I highly recommend labeling EVERYTHING with washable name stickers. These seem to be super durable and I’ve even used them to label Sophie’s backpack, lunchbox, and both parts of her water bottle (lid + cup).
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MEALTIME
Practice opening/closing/using all mealtime gear independently (water bottle, lunchbox, etc) if those items are new to your kiddo.
Sophie is a fairly selective eater so I was planning to pack a LOT of peanut butter sandwiches in her lunchbox before discovering that her school has a no nut policy. I totally understand why (and feel terrible for anyone with a nut allergy in their household — my heart goes out to you), but that meant I needed to fully revamp my lunch packing plans. Thankfully, there are a lot of online resources that offer nut-free toddler meal ideas and I’m so grateful for them! You mamas are the real MVPs!
If you have a selective eater as well, try incorporating these foods into their rotation ahead of school starting so that they’ve at least had some exposure and aren’t totally blindsided by new food items when they open up their lunchbox.
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TIPS & TRICKS
I have honestly been kind of dreading the start of preschool because new things / transitions aren’t our favorites around here. Sophie is such a tender heart and is a big Mama’s Girl so I anticipate that her separation anxiety will be on overdrive on the first day (/week?) while we navigate all of the new things! And of course I know I’m going to be worried sick about her feeling anxious and scared while we’re apart — there will definitely be tears shed by both of us.
I gathered some useful resources for handling the start of preschool with Sophie and thought I might share them with you:
You’ll definitely want to attend the school’s Open House to meet teachers, show your kiddo where their classroom is, where they’ll store their things, etc. — it will help you both start school with confidence.
Read back-to-school books ahead of time and talk about [generally] what to expect from the experience.
Make / assemble gift for teacher(s) together.
One sweet way to handle being apart is to utilize mommy & me bracelets which you can gift to them in the first day to make it feel extra special.
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I found great insights for handling drop off as well as some tips for managing “restraint collapse” after pickup.
I appreciated these weeknight dinner ideas to help simplify meal planning, some additional start-of-school tips here, with even more advice from experts here, here and here!
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ILLNESS
Schools are such Petri dishes so the spread of germs is largely unavoidable. I encourage you to prepare your medicine cabinet for inevitable illnesses, for the whole family.
Additionally, encouraging regular (proper!) hand washing, and sneezing / coughing into elbows will do wonders to minimize the spread of germs. Having sick kiddos is so stressful… we try to avoid it at all costs!
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CELEBRATORY FIRST DAY FUN
Send them off on their first day with a fun breakfast celebration! I gathered a lot of inspiration from this post by emelbe design and this post by The Mama Notes.
Sophie isn’t a big breakfast eater so I kept it simple and served her some milk, “special” Cheerios, and berries.
I also loved this additional idea by Somewhat Simple to have a fun surprise to greet them when they return home after their first day of school. If you suspect that your munchkin will be fussy at pickup, maybe bring the party to them and pack a fun snack box for them to enjoy on the drive home.
I loved this list of simple and fun back-to-school traditions too, which may feel more organic for your family.
I also love the pictures of littles with their First Day Sign or holding a First Day Pennant / Banner so I knew I wanted to start that tradition every year for our girls. It will be so sweet to see how they grow up — both over the course of their school year, but also over the years! Even though Chloe is years away from starting school, I already ordered her matching custom first / last board from the same seller (just in case they change their designs or stop selling altogether!).
By no means do I think you should feel pressure to set up both of these little celebrations (or any at all!), but I wanted to share both options because not everyone has their sh!t together in the mornings (myself included!), so a fun afternoon greeting may work better for some families.
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First Day Teacher Gifts
A teacher gift is such a kind gesture to start the year off on the right foot. This is neither needed nor expected, but always a very nice thing to do. I think that @occasionsbyshakira always does an amazing job coming up with gift ideas — I always feel so inspired by them!
I linked a few of my favorite printable card holders below in case you’re looking for some gifting inspiration!
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I also wanted to mention that we have used Susie’s “Playing Preschool 1 & 2” curriculums at home and loved it! We plan to continue to do these activities in the afternoons after Sophie has woken up from her nap, even on days that she has gone to school!

I look forward to making the First Day Celebration a tradition for both of our girls. It’s fun to start the school year off on a positive note and get kids excited for the year ahead!
I’m still in disbelief that our first baby is already in preschool… didn’t we just bring her home from the hospital?? I hope that everyone else has a great start to their school year and that things are going smoothly for all other caregivers also navigating this milestone for the first time — solidarity!
Sending big hugs —
xx, Natalie
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