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.

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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. Varsity Denim Hoodie Jacket – The perfect denim jacket with a cool retro feel. 
2. Embroidered Apple Dress – I love the scalloped collar on this dress. 
3. Red Apple Shirt – The little embroidered apple is just so cute!
4. Apple Skirt – I love how easy this pull on skirt is to get on and all of the colorful apples are just adorable.
5. Raglan Sleeves – Such a great classic look for boys and girls.
6. Canvas velcro shoes – These pair easily with so many looks. 
7. Print Leggings – These come in so many prints and are a great staple.
8. Short Romper – These have the option to add a personalized monogram.
9. Scalloped Edge Grosgrain Bow – I love the scalloped edges and these come in so many colors.
10. Bracelet – this is DARLING.  Plus there are personalization options too!
11. Apple socks – I love how subtle these are.
12. Pencil tee – Great price point!
13. Kids Nap Dress – Such a comfy and cute way to do a mommy and me look.
14. Hunter Rain Boots – Say goodbye to soggy sneakers!
15. Cardigan – Comes in several sweet colors.
16. Boys shoes– An affordable Sperry alternative.
17. Unisex Smiley Tee – I love the colors on this one!
18. Pink Sequin Apple Dress– great deal!
19. Red Shoes – We have and love these!
20. School Collared Shirt – You have to zoom in on this. It has small beakers and science equipment on it – so cute!
21. Pencil Hair Clip – I love cute themed accessories like this.
22. Toddler joggers – Joggers are the perfect fall preschooler pants.
23. Gold Star Sneakers – I love this rose gold color.
24. White converse tennis shoes – I love a good plain shoe option that can pair with anything above. 
25. Long sleeve red apple dress – The apple socks above would love so darling with this dress.

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. Back to school knit pajamas 
2. Crayons Long Sleeve Set 
3. Colorful alphabet
4. ABC Kickee Pants
5. Big Apples 
6. Hair Bow
7. Bus to school pjs
8. Pencil Hair Bow
9. Rainbow ABCs
10. Pink & Green Apples Nightgown
11. Pink School Days
12. Felt Apple Clip
13. Apple pants set
14. Yellow stripes
15. Happy Face slippers
16. Education Express
17. Numbers Shorts Set
18. School Buses Shorts Set