14 Fun & Clever Ways to Get Your Kids Ready for the First Day of School

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Kid eating sheet pan pancakes

The first day back to school may be drawing near, but that’s no reason to be sad! With these fun and clever ideas, tips, and tricks, your kids will be way excited to start their next school year!

1. Ease the separation from home with a love note.

notes in kids lunch meals

“We slip notes in lunchboxes! It’s a nice way for the kids to feel that even if they’re not loving school that day, we’re always still thinking of them.” – Jamie

Hip Tip: Making lunches just got a whole lot easier with these lunchbox hacks.

2. Go school supply shopping together.

girl holding various school supplies writing utensils

“Growing up, my mom always took me school supply shopping. It was always so exciting to pick some colorful pens and other accessories that I would enjoy using that school year. It made me excited for the first day of school, too, so I enjoy getting to do this with my kids and seeing their excitement.” – Sara

Hip Tip: Make sure to print our 2019 Back to School stock up prices list to help you shop this year!

3. Start building a community early.

mom with kids at a small picnic

“One thing the school does which I LOVE is a “meet the teacher” day. The week before school, students can see their classroom, meet their teacher, find out who is in their class, and play on the playground with their friends. There are snacks and a really fun atmosphere for families and activities for the kids. It does wonders to alleviate the first day jitters (especially for elementary kiddos). I wish more schools did this!” – Jenna

4. Take lots of pictures!

girl and boy ready for first day of school with chalkboards

“I take pictures of my kids together and also separate to see how much they’ve grown by the end of the year.”  – Alana

“I love taking the first day of school pictures and always make sure they have a fresh cut, too.” – Lina

Hip Tip: Amazon is a great and quick source to grab some last minute chalkboards!

5. Pick out a new backpack or lunch box.

grandma with boy and girl with lunchboxes

“My mom always takes the kids and buys their backpacks and lunch boxes! It’s a fun way to show off their personality and personalize their belongings. Plus, it’s a fun way for us to get the grandparents involved in the big day, too.” – Erica

6. Plan one last getaway.

dad and son in tube in water slide

“Once school starts, we don’t travel much, so it’s fun to pick a somewhat local place for a staycation and have one last hoorah before school starts. It also gives the kids something to look forward to.” – Sara

Hip Tip: Great Wolf Lodge is always having amazing deals, and the kids will definitely have a blast!

7. Pamper them before the first day.

two girls in pink robes having pedicures

“I’m a boy mom, so we just do some fresh haircuts. However, my friend who has all daughters does a mommy-daughter spa day before school with face masks & painting nails which I think is adorable and so fun!” – Alana 

Hip Tip: We are huge fans of these easy and affordable Impress nails!

8. Make dinner or dessert fun the night before.

spatula with delicious sheet pancakes

Go out for ice cream, or make some of Lina’s sheet pancakes for dinner. Treating the kids to a fun and untraditional dinner may make them more likely to open up about any first-day jitters they’re having.

9. Throw a character-building ice cream party.

boy with jars of candy

I love how Lindsay at Run Lucas Run (shown above) created a fun and unique ice cream party that any kid would love. Invite all of their friends and let them pick the toppings or “attributes” that they want for their upcoming school year. Will they choose chocolate chips for bravery, gummy bears for happiness, or all of them?! 😍 Read more about her party at Lindsay’s site.

10. Buy a huge graduating class t-shirt for them to wear.

two boys wearing blue class of 2031 shirts

Not only will your little one look super adorable in one of these class shirts, but you’ll get to look back over the years every time they’re worn it to see just how far they have come (and how much they’ve grown).

11. Get to really know your kids with a questionnaire.


No matter the age, kids love to share their favorite things! Whether you take a video as this Dad did on Popsugar, or they write it all down, asking them questions about their favorite food, subject, best friend, etc. will make for great memories looking back. (Hey, I’m not crying, you’re crying. 😭)

12. Get silly with a home fashion show.

girl with tons of shopping bags outside

One thing I love doing for a new school year is getting to buy new clothes. Make it fun and silly by setting up a runway at home and let the kids show off their favorite looks for fall.

Hip Tip: You need to check out our 14 Macy’s shopping tips to save you money before you head to the store!

13. Let them pick the lunch menu.

hand holding bags of goldfish and popcorn

There’s nothing like getting to school and unzipping a lunch that has all of their friends drooling. Take them to the store and let them pick some fun snacks. All in moderation, of course. 😉

14. Decorate their senior car.

silver car decorate with banner and senior

Older kids need to have their fun, too! Deck out their wheels and make their beginning of their last entrance to senior high something special to remember.

Bonus: Do something with your spouse on the first day.

man and woman smiling and kissing

You’ve spent the entire summer as a family unit, now is you’re first chance to enjoy your spouse all to yourself. Go out for an adult brunch, take the day off work, make time for coffee together, or go for a walk.

Hip Tip: Date your spouse after the kid’s go to bed with these 10 different date nights in a box!

Check out this huge list of school supplies you’ll want this year (at stock-up prices)!

About the writer:

Sara is a self-taught blogger & photographer and brings 9+ years of experience to her craft. Her work has been featured in numerous esteemed publications, spanning building, travel, and fashion. Beyond her creative pursuits, Sara’s primary mission is to empower others to embrace a toxic-free & sustainable lifestyle.

Join The Discussion

Comments 13

  1. Michelle

    I will have a Senior, Freshman, and Kindergartner so the level of enthusiasm is different with each kid… My youngest is so excited she is already planning what to get her teacher for Christmas! My oldest kids have always liked school but I always try to have a little present ready for them when they get home on the first day😉😉

    • Amber (Hip Sidekick)

      How sweet! Thanks so much for taking a moment to share with us, Michelle!

  2. Sarah C

    We just got out of school 6 days ago lol.

    • Kathleen

      We just got out 2 weeks ago 😂

    • Carrie G.

      Us too! These back-to-school posts are messing with my anxiety! 🙃

    • Haseena


  3. Nita

    I know it’s a shame. We spend so many months waiting for winter to be over, on the northeast anyway.. then it’s finally over, it finally gets warm in June..then boom by July 1 its back to school advertising. It’s like huh?? Let’s enjoy summer for a minute maybe.

    • Kim

      It’s been summer since end of February and hit almost 90 degrees for the first time in March. So I’m ready for summer to be over lol.

  4. Nita

    Appreciate these posts, it’s just psychological, the anxiety like someone said.

  5. Kay

    I like the character-building ice cream party idea the best. Most of the rest of the ideas aren’t as character-building or frugal. I often think of the many poor kids who can’t afford all the new school supplies, new clothes, pampering activities, new lunch boxes, getaways, etc. I also like the dating idea. Overall, thank u for putting together this post.

    • lisa

      one thing my family does is a community service activity together such as donating school supplies for kids to a local agency or school.

  6. Jessica G

    Whhhhhaaaaaahhhh… that video totally made me cry. Love this post! Another tip that my my mom did with me and my sister all threw my school years (especially jr high). We always bought school supplies/new backpacks if needed but we only really bought a first day of school outfit plus shoes. We didn’t buy all our new school year clothes during the summer, because really when it comes to Jr high/high school fashion you don’t know what really going to be popular/what your friends are wearing until you get there and everyone is wearing it. It would be a bummer to spend $200 or more on clothes we didn’t even want to wear because we wanted something else a week later. My mom was smart and very frugal we stopped at yardsales/thrift stores for our jeans before we hit the clearance racks!

    • Amber (Hip Sidekick)

      You’re right! I love that tip! I don’t buy everything needed for the year right away either. However, I will snag any HOT deals that pop up, which may not be available for less later. Thanks so much for the helpful suggestion!

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