What to Wear to Elementary School

Most years, when August rolls around, we do all our back to school shopping. I like to go on one-on-one shopping dates with each child. Before we head out, we go through their closet. We see what still fits, we pack up items to donate (or save for a younger sibling), and we make a basic shopping list — a typical list might include socks, a new pair of jeans, a hoodie, and 2 tops. On our date, we pick out something specific to wear for the first day of school, and do our best to find the basics on our shopping list.

But this last August was crazier than usual. We didn’t get home from France until August 20th. Then school started a couple of days later. And suddenly, Ralph and Maude were both moving out of the country!

So school shopping didn’t really happen. Knowing we wouldn’t have time for real dates, we picked out first day of school outfits for Betty & June while we were being tourists in France. And then, they simply made due with what was in their closet until we had time to shop. Which didn’t really happen until the holiday break! Happily, with two older sisters, they both had plenty of hand-me-downs to help them along.

We took these photos last month (in January). Betty is in 5th grade this year. June is in 1st grade. And this post is all about what to wear to elementary school.

On June:
Buffalo check dress from H&M. Gymboree Sweater from ThredUp. Rainbow socks, hand-me-down from Betty. Red high-tops from Old Navy. This dress was what she wore on the first day of school.

On Betty:
Denim Jacket from GapKids. Red cheetah print dress by Kate Spade from Nordstrom. Black leggings from Old Navy. Black flats, hand-me-down from Olive.

On June:
Sequin heart sweater, striped leggings, striped socks from H&M. Tweed shorts from Uniqlo.


On Betty:
Jumpsuit and pink high-tops from Old Navy. Layering tee and polka-dot socks from H&M.

On June:
Polkadot dress with claw pockets, black leggings, pink socks, from H&M. Silver slip-ons from Old Navy. Purse was a Christmas gift from Oscar.


On Betty:
Pink tee with gold lettering, grey print leggings, polka-dot socks from H&M. Cardigan, a hand-me-down from Olive. Perforated leather slip-ons from Vans. Every time Betty practices music for 20 days, she gets a new charm for her bracelet.

On June:
Raincoat from Amazon. A raincoat was one of her main requests for Christmas. Thank goodness. It’s been so insanely rainy this year!


On Betty:
Striped dress from Nordstrom. Big check leggings and slip-ons from Old Navy. Socks from H&M.


On June: 
Gingham trench coat from Uniqlo. Striped top from Nordstrom. Polkadot overalls from Target. Blue stripe socks from GapKids.

On Betty:
Jeans and striped button-down from H&M. Striped sweater and pink Converse from Nordstrom. Parka from Uniqlo.

On June:
Black jeggings from Uniqlo. Animal print top from H&M. Hiking socks and high-tops from Old Navy. She doesn’t need glasses, but likes to wear these sometimes. They are just sunglasses with the lenses removed.

On Betty:
Pink layering tee from H&M. Jacket and short set from Sergeant Major. This is what Betty wore on the first day of school. We bought it while we were in France for the summer.

Oh my goodness! So many cute things. I love doing these photo shoots with my kids. I hope they will love looking back at these and seeing how styles changed over the years, and how their hair changed, and how tall they were that year. I love that June is missing her front teeth in these photos. Both of her front teeth came out a couple of days before Christmas — so if we had taken these photos in the fall, she would have had a totally different smile. : )

What are your kids wearing these days? Do any of these pieces look familiar?

P.S. — What to wear to Middle School and High School is coming right up! Want more? Check out all our What to Wear to School posts.

8 thoughts on “What to Wear to Elementary School”

  1. I love these posts! I am interested in your thoughts and if you have any experience dressing a child who is strong willed and has their own idea of what they will wear. I have a spunky stylish 4 and a half year old who carefully puts together some pretty crazy outfits, and will have NO help or suggestions from me, refuses to wear black, gray and other “sad colors” :) I love her sense of style and that she can express herself that way, but may sometimes Id love to see her in a cute pair of overalls! Have any of your kids been this way?

    1. My five-year-old is very strong-willed when it comes to clothing. I tried for a while (a long laborious while) to steer her in a certain direction (super cute jumpsuits, drop waisted French-inspired dresses) but those clothes stayed in her closet while she wore and rewore and wore once again her favorite looks — crazy legwarmers or tights, opera length gloves, floral sundresses over striped long underwear… and don’t forget one of mamá’s headscarves as a cape and swim goggles! I would silently groan, consider hiding the gloves, try to sweet talk her into wearing the amazing jumpsuit that I oh-so-wish was made in my size.

      And then I just stopped.

      If she wants to wear 5 headbands and a sweater dress over a tutu, what is the harm? This is also the girl who is fearless in her circus class, beyond generous with her love and can will sing “The Lion Sings Tonight” to anyone and everyone who will listen. She’s got this. And if it takes some reds + oranges + blues + purples + greens all mixed together to make her feel good, so be it!

      So I apologize if it’s not what you wanted to hear… but my advise is to just go with it! Donate the overalls to a kid who will wear them, stock up on opera gloves and learn to say “Isn’t it marvelous?” when other parents raise their eyebrows at your kid wearing 3 skirts and a cape.

      1. PS I didn’t include WHY I stopped fighting the fashion whims of my wee eccentric.

        1) I was exhausting myself every morning through exasperating negotiations and both of us were starting off our day in an antagonistic and defeated mood

        2) I decided to pick my battles… my daughter goes to a rough and tumble Montessori school in a nature preserve and it is “important” to me that her hair is up off her face in a secure ‘do that will last the entire day. I realized that if I don’t push it on the clothes, she is much more willing to sit and let me braid, pin and secure her hair before bouncing out the door. Fighting her on clothes always led to a fight on hair… now that I give her a happy thumbs up on her outfits, she is in such a positive mood, I don’t have negotiate or “force” her to let me do her hair.

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