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As summer comes to an end, those of you with 2 and 3 year olds are gearing up to send your little ones on their way to school for the first time.  It’s truly a bittersweet moment.  My son is 3, he is our first, so I asked a few friends for some advice on items to pack for his first day.  There are some things I never would have thought of, so I’m so grateful for all of the suggestions that were sent my way.  I spent some time researching and even testing out some of these products in advance this summer and here is a list of my favorites and must haves for his first day.  Besides the 20 boxes of Kleenex that I’ll be packing for myself as I try to contain the river of tears that will be flowing down my face! Where did the time go???


I originally purchased my son a backpack from Pottery Barn Kids.  He used it during the transition week at school and it was way too big for his toddler frame (and he’s a big 3 year old).  I’ll probably store it for when he starts kindergarten.  So I was back on the hunt for the perfect size bag for a toddler and I came across the Herschel Supply bags for kids.  They come in the cutest patterns and they are perfect for smaller children, preschool age.  Some of my friends who have kids in school already, even mentioned that they felt their kids didn’t need a bag at all at this age, so it’s up to you whether or not to make this purchase! I did, so he can bring his crafts and stuff home and his lunch box and I can refill any supplies he might be running low on.  Also, another cute and more affordable option is the Skip Hop bags which come in a lot of fun animal characters for kids for $19.99, whereas Herschel bags cost $40.00.



Alternatively to a backpack, you can just place a tote in your child’s cubby so that his work, or any dirty clothes and lunchbox can be sent back home to you.  You can purchase a cute tote, or just use a reusable grocery bag or a tote you have around the house to save.   You can even buy a solid tote and decorate it with your toddler to make it extra special!


Two pocket folder:

This is a good idea to have for permission slips, class announcements, kids art work to be stored and sent back home to you.  A folder will keep everything in one place and organized.


Family photos:

Great to tape to your kid’s cubby so he/she can see familiar faces when they arrive to school each day. It’s just a nice way to make your child feel at home while they’re at school and to make their cubby truly feel like their own personal space.


Extra clothes such as a sweater or jacket in case it gets chilly, extra pants, shirts, socks, shoes in case of accidents.  I wouldn’t buy super expensive, fancy clothes for preschool either.  All children should and will get messy at preschool, its part of the experience!  They will be playing outside and doing tons of messy crafts inside so it’s inevitable that their clothes will get messy.  So try and look for good sales and affordable clothes so you don’t have to worry too much about the mess that they will make.  Old navy has a back to preschool sale with their $4 and under sale.  There are large selections of t-shirts, shorts, socks, etc. for under $4.  Gap has a 40% off sale right now, no exclusions online and let’s be honest their in store sale section is always amazing anyway!  Target is also a great place to get cute yet affordable clothing for kids.  But my all-time favorite for kids clothing that’s incredibly affordable and stylish is H&M.



Some schools might have particular guidelines for shoes, but I would say for preschoolers a good set of rules to consider when purchasing shoes are no sandals, and no laces.  My 3 year old son is already in a size 11 so a lot of the shoes are made with laces.  So I purchased Laceez, you can find them on Amazon, they are no-tie shoe laces which we’ve put on all of his Nike’s.  We also love converse as they have a bunch of velcro options even in the larger shoe sizes.  And if you want something for the warmer months when the kids might be swimming or playing with water outside, Natives are a great water shoe that isn’t a sandal. We also love Naturino shoes. They are durable and will last your toddler the entire school year.



If you plan on making your child’s lunch, there are some great lunchboxes out there. For some amazing lunchbox inspo, check out Planetbox Instagram page.  It’s pretty unreal how crafty some parents are with their child’s lunch.  They are rather pricey however ($79.00), so I went with a more affordable alternative and purchased the Bentogo Kids lunch box for $27.99. Another great affordable option is the OmieBox which has an insulated thermos in the middle, which runs for $39.50.  Great if you want to prepare foods that need to stay warm like soups or pastas.


Water Bottle:

You’ll want something leakproof that will also keep drinks cold for the entire day. My favorite is the Thermos Foogo stainless steel 10 ounce straw bottle from amazon for $11.79.  Every mom I talked to agreed that this was their favorite cup for school!



I got my son a set of personalized sticker labels on sale on a while back.  There are some great non-iron options on amazon, and I’m sure you can find some super cute personalized ones on websites like Etsy.  Or you can just get a permanent sharpie and write your child’s name on the label itself, simple and easy solution!


Sleeping bag, or nap mat:

I was just about to order a cute sleeping bag but my friend mentioned that those can be super bulky in their little cubbies.  So the better option is the nap mat, since it’s more compact and has a pillow attached as well.  Nap mats were also highly recommended by the teachers at my son’s school.