I started this series on first day of school outfits when we were all locked down in 2020, and incorporated pajamas and other fun items, and it has become a tradition now to tie in fun items for both wearing at home and school. My older kids wear a uniform, so I now love having the fun school themed items in small ways and pajamas. Hopefully you find something festive and fun in this post.

This post may contain affiliate links – updated July 2025

First Day of School Outfits

If you are a mom with school aged kids, then you probably encountered the last day of school photo issue this past spring…and here we are again still trying to navigate the world that is just so far from normal.

I am a firm believer in celebrating back to school – no matter what that looks like for your family, and will be sharing some ideas and resources to tackle the school year for ALL families as the next month goes on.  I am hoping that as a community we can all come together to really support every family in the choice they make (OR are forced to make) in what this fall looks like for their family.

For first day of school outfits I tried to share some great traditional looks as well as some more casual stay at home looks!

First Day of School Outfits – At Home Addition

So when it comes to being at home – I don’t think you necessarily have to embrace things ‘normally’.  I think sometimes the joy comes into leaning into the abnormal, and finding the small wins that way.

This round up contains so many gorgeous outfits, but it also contains some really inexpensive play clothes versions, and lots of pajamas.  Let’s face it – the pandemic has normalized lazy clothes and pajamas, so why not make them festive.

No matter if you go festive like one of the options in this post or you go stay in pajamas to homeschool- looking back on how much your kids have grown over the year is so fun, so snap the picture.  

I’ll start with the back to school clothes – both casual with some shorts and joggers- and a bit more festive with bows and the cutest kids’ varsity jacket I’ve ever seen.

Shop Back to School Clothes

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1. Denim Jacket – The perfect denim jacket with a cool retro feel. 
2. Scalloped Edge Bow – I love the scalloped edges and these come in so many colors.
3. Blue Truck Shirt – The little embroidered truck is just so cute!
4. Red Stripe Shirt – Such a great classic look for boys and girls.
5. Boat Shoes – An affordable Sperry alternative.
6. Apple Dress – I love the ruffle sleeve on this dress. 
7. School Themed Bow – this bow is too cute!
8. Blue Heart Skirt – I love how easy this pull on skirt is to get on and all of the colorful hearts are just adorable.
9. Leggings – These come in so many prints and are a great staple.
10. Smocked Romper Onesie – I love the embroidered detailing on this one!
11. Bracelet – this is DARLING.  Plus there are personalization options too!
12. Apple socks – I love how subtle these are.
13. ABC Tee – I love the colors on this one!
14. Worm in Apple tee – Great price point!
15. Cardigan – Comes in several sweet colors.
16. Toddler joggers – Joggers are the perfect fall preschooler pants.
17. Hunter Rain Boots – Say goodbye to soggy sneakers!
18. Canvas velcro shoes – These pair easily with so many looks. 
19. Kids Nap Dress – Such a comfy and cute way to do a mommy and me look.
20. School Collared Shirt – You have to zoom in on this. It has small beakers and science equipment on it – so cute!
21. Long sleeve red apple dress – The apple socks above would love so darling with this dress.
22. Pencil Bow Headband – such an adorable accessory! 
23. White converse tennis shoes – I love a good plain shoe option that can pair with anything above. 
24. Red Shoes – We have and love these!
25. Gold Star Sneakers – I love this gold color.

And now for the back to school pajamas! Whether you’ll be homeschooling or just celebrating the back to school season, these cozy options will get your family in the school spirit!

Shop Back to School Pajamas

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1. Navy Blue ABC Pajamas
2. Pink Gingham Bow ABC Pajamas
3. Coloring Pajamas
4. School Supplies Pajamas
5. Pink ABC Nightgown
6. Pencil Hairbows 
7. School Themed Pajamas
8. School and Bus Pajamas
9. ABC Pajamas
10. Bus Pajamas
11. Animal ABC Pajamas
12. Pencil Headband 
13. School Bow
14. Smiley Slippers 
15. Apple Pajamas
16. Pink Hairbow 
17. Blue Gingham Apple Pajamas
18. Letters Pajamas