What to Wear to Elementary School


Photos and text by Gabrielle.

Woo hoo! The annual What to Wear to School photos are ready!! For those of you who are new here, I’ve been writing What to Wear to School posts basically since I started blogging. You can find them all here. The series has changed and evolved over the years, and this year is no exception. For the last two years, I did 3 posts featuring two kids in each. But we’ve made some big changes:


1) Now that he’s a college boy, Ralph has officially retired from the series.

2) Since Oscar, Betty and June are all in the same school for the first time since we moved here (and probably the last time — Oscar is off to middle school next year), I thought it would be fun to feature them all in one post: What to Wear to Elementary School!


I went on back-to-school shopping dates with each of the kids, and then we came home and put together 4 outfits for each of them.


Oscar is ten, and in 5th grade. Betty is nine, and in 4th grade. June is five, and in Kindergarten. Read to jump in? Let’s do this!



For Oscar, I had the best luck at H&M this year. Oscar is wearing sweat-pants, a green striped tee, socks, and hat — all from H&M. His shoes are by Vans (this particular design is great for hiding dirt).



Betty is wearing black pants, a striped shirt, and grey hoodie — all from Uniqlo. These pants are THE BEST! Olive has the same pair and so do I. And we all wear them a ton! They come in lots of patterns and colors, though we all own the black version. They’re a thick knit, but they’re sort of cut like jeans — sort of trouser-leggings, and they don’t fit as snug as true leggings. They are super comfy and have an elastic waist, but look finished. Five stars!

She’s also wearing shoes by Vans (the little stars are metallic), no show socks, and her backpack is by Herschel. It’s a hand-me-down from Maude.



June is wearing a green crepe dress from Old Navy, a hand-me-down grey cardigan from Zara (similar here), apple socks from Gap, and red shoes we picked up in France before we moved. I’ve been saving them and I’m so happy they fit her just in time for Kindergarten!

I want to tell everyone to go out and get this dress! It’s so adorable I can hardly stand it. And it comes in a rose color too (the colors in the online store are NOT accurate). June wore this outfit on the first day of school.

I should mention, for the girls, I ended up having fantastic luck at Old Navy — so you’ll see a lot of their clothes in this post. Sometimes I walk through their stores and I’m not into it at all, but their collection this fall is the best I’ve seen in years. I’d love to know who the designer is who made it happen. It’s so good! If you’re nervous about quality, stick to the 100% cotton options — they’ve all washed up very well.



Oscar is wearing dark jeans, a collarless button-down, socks, and a green puffer-vest — all from H&M. His slip-ons are from Gap (they were part of their summer collection). I think this is his favorite of the all the outfits. It’s been quite warm here, but if the temperature dips at all, he’ll find an excuse to wear the vest. : )



June is wearing a quilted skirt from Old Navy, a light pink tee and chambray shirt from H&M, striped tights (hand me downs from Betty), and her shoes are by Vans.

One note on the shoes: The sharks glow in the dark! In one of the photos you can kind of see them glowing.

I have to say, June’s poses are pretty fantastic. She came up with all them herself.



Betty is wearing a pink jacket, heathered sweater, and dark teal layering tank from Old Navy. Her pants are hand-me-downs from Zara (gosh I miss having a good children’s Zara close at hand). And her shoes are from Cole Hahn. She’s had these shoes for awhile now.

I have the hardest time finding non-synthetic sweaters for the kids, but this one is 100% cotton! And it comes in two colors.



Oscar is wearing grey jeans, a heathered green henley, and a striped hooded sweater — all from H&M. (I wasn’t kidding about having good luck there for him!) His shoes are from Gap (part of their 2015 Spring collection.)

Under those grey jeans, he’s hiding some really awesome socks (see the red stripes below)! The socks are from Uniqlo (go see, they’re really cute!).



Betty is wearing a chambray shirt and vented sweater — both from Old Navy. It’s another 100% cotton sweater, and there are 3 colors! Her grey pleated skirt and striped socks are both hand-me-downs from Olive. (You can spot them in earlier What to Wear to School posts.)

Betty wore this outfit on the first day of school this year. It’s a great outfit and she feels great in it.



June is wearing grey jeans, floral tee, and pink cable-knit sweater — all from Old Navy. (Yes, this is another 100% cotton sweater!). Her shoes are silver Saltwater Sandals.



Oscar is wearing long, linen-look shorts (I don’t see them online, but it seems like there were plenty in-store), striped tee, and blue micro-stripe button down — all from H&M. His sandals are by Crocs.



Betty is wearing a red tee from Gap, a white denim jacket from Target (I found it back in May), and striped leggings from Crewcuts. She’s been wearing the leggings since Christmas and they’re still going strong! They’re thick and really good quality. Similar here.



June is wearing a pink polka dot tee, grey leggings, and a grey check button-down — all from H&M. (If you’re hunting, the button-down is from the boys department.) Her socks are from The Gap (they have such good socks!), and her shoes are by Vans.

You may have noticed that much of June’s wardrobe is in the same color palette — it makes for nice mixing and matching!


And there you have it: What to wear to elementary school — or at least, what to wear to Kindergarten, 4th grade and 5th grade. Hah!

How about you? Did you spot any of the same pieces as you did your back-to-school shopping this year? Do you have a favorite outfit in this post? I’d love to hear!

I should also tell you, I haven’t shot photos of Olive or Maude yet. Maude only had one thing on her back to school list: running shoes. Hah! And Olive is in a new-to-her middle school this year. It’s a public school, but it has uniforms. (It’s kind of exciting for us, because we’ve never had a school with school uniforms before.) We’ll probably still do a shoot with Maude and Olive, but it feels less urgent since Maude isn’t feeling that new-clothes-excitement, and Olive’s outfits are so similar to one another. We’ll see what we come up with!

P.S. — Want more? You can find all the What to Wear to School posts here.

43 thoughts on “What to Wear to Elementary School”

  1. How awesome– I love this series! And as someone who wore uniforms for 9 years, I think it would be pretty interesting to see how she can add her own flair. I ended up wearing basically the same thing every day (skirt if it was warm, pants if it was cold) but changing up shoes/socks/jewelry/hairstyles makes it fun. As for Maude, I’d actually love to see her running shoes! And any running/workout looks, since that’s what she’s into. Although I know sometimes it can just be a pair of shorts and whatever t-shirt is clean :)

  2. Wow, time goes by fast – they’re so grown up! :( They’re turning into awesome tweens (and big kids) though! Loooove the outfits and Old Navy tips!

    I also agree with Sarah – Maude can show off her running outfits! :)

  3. I really like Oscars outfits. So cute, but yet so boy. I find it hard to find cute outfits for boys. So many stores fill their boys clothes with characters.

  4. Ok, I’m going to pose a question, because I have a little *ahem* lady in PreK – in our public school here in WV – and she would wear a skirt every day if I let her…how do you deal with the skirt issue? And by issue I mean the dreaded “Panty Flash”? I love that a lot of skirts for little ladies are now skorts, but when they’re not I try to ad in a coordinating pair of bike shorts (summer) and/or leggings (winter). I’m kinda wondering if I overdo it? Or do other moms do the same thing? I, for one, remember the playground in elementary school being one of those places where you had to watch for the little “gentlemen” while you were climbing on the monkey bars…they weren’t against taking a peek if you made it too easy…even if that was 30+ years ago…

    1. You’re not alone! My daughter wears playground shorts (probably the same as bike shorts) or leggings under skirts. She’d be flashing the world otherwise!

    2. My daughter was born a week after Baby June, so I have a soft spot for her. :) As for skirts and dresses, I always make my daughter wear bike shorts (Hanna Andersson seems to be the only store that sells them!) or leggings under her clothes. I feel bad imposing this new requirement since Kindergarten started…but it has been a concern of mine! My daughter hasn’t balked at the extra layer yet, but I am wondering if I will have to tell her that we don’t need to flash others on the playground.

    3. My girls wear skirts or dresses almost every day with either bike shorts or leggings/tights underneath for the same reason. If they’re not hanging upside down on the monkey bars, they’re doing flips and somersaults – or some other activity that would result in flashing underpants!

    4. Good question! Yes, my girls like to wear short knit shorts under their skirts. They want to be free to be active, but they also like dresses and skirts. We stock up on very short knit shorts from Target when they come out in the spring/summer.

      1. They make little shorts called Playground Pals (or something similar) that you can get for under dresses/skirts. When my girls wear and/or scrape holes in the knees of their leggings, I cut them off above the hole and use these under skirts and dresses. Not beautiful, but functional!

    5. My daughter is in high school and still wears bike shorts or leggings under a lot of her skirts, and by her own choice. She likes the cute skirts in the Juniors section but finds them too short to be practical for a busy school day. While there are no monkey bars, there is sitting on the floor, walking up and down open stairs, etc., and with the thin second layer she doesn’t have to do a constant skirt check.

    6. I teach Pre-K, and all of my girlies *and I* wear shorts under our skirts/dresses. It’s just so much easier to run, swing upside down, and be awesomely active without sacrificing fashion or showing off something we want to keep private. My shorts are so comfy that they’ve even started creeping under my grown-up dresses in real life!

    7. My daughter wears something under her skirts and dresses as well. We’ve really liked the Old Navy biker shorts as they tend to be a little tighter and shorter than the Hanna Anderssen ones. The ones from Hanna are always loose and sticking out the bottom, which drives me a little crazy because I have a little 4 year old that is NOT into matching! :)

  5. I LOVE the Saltwater brand sandals. This was the second summer in a row I’ve gotten them for my little one. They have been through so much — water, dirt, potty training accidents — and always clean up nicely. And they’ve held up so well that they will be a great hand-me-down for my younger daughter.

    1. Saltwater Sandals are the best. They’re one of the few shoes that my oldest doesn’t destroy and can actually be passed on to my younger girls. My girls all wear them and even me too! They’re so comfy, come in great colors and the style is so simple they go with everything :)

  6. I love your comment about June’s mixable wardrobe! My daughter started JK this year and is very determined to choose her own clothes – which I try to support. After a few crazy outfits this summer I made very purposeful decisions for her fall wardrobe – it’s almost entirely mix and match.

  7. You are so right about the Old Navy line this fall. I feel the same, either I see a ton I like or nothing – and quality is always a concern. We had finished our Back-to-school shopping and stopped into Old Navy just to look for some long shorts (which I now realize aren’t that readily available out of California where we just moved from) – and we walked out $150 poorer because there was so much fun stuff there. Hoping it all gets lots of wear. Right now it’s been so hot that it’s still summer shorts and tees every day. Looking forward to seeing that stuff go away and to get into some more stylish layering. :)

  8. Oh, June… those poses are the best!

    I still can’t believe that she is in school already. That said, my middle daughter just started Transitional Kindergarten (she just misses the cut off for real Kindergarten) so I guess I can believe it :)

    Growing up in Australia where almost all schools have a uniform I’m still not used to this whole “back to school” shopping thing. I don’t really buy my kids new clothes for the new school year. I just buy them clothes when my favorite stores have sales throughout the year. I did buy them new backpacks and shoes for back to school though. I guess I’m easing myself into a “new to me” tradition!

  9. When you take your kids on shopping trips, how do you handle their sometimes questionable fashion choices? I can’t imagine your kids making any, but when I take my daughters shopping, they inevitably want something bright and (to my eye) ugly, usually with a cartoon character involved. Or they pick out tops and bottoms that really don’t work together, or something really impractical that I have to say no to. I’ve often found it easier to shop without them, and they usually like what I bring home, but that’s not really teaching them anything. Thoughts or advice?

  10. I love reading the outfit posts, so helpful to find clothes for kids. And your kids are adorable and Betty has gorgeous, gorgeous hair! Love the thick braid!

  11. Love, love, love these posts! Thanks so much for doing them. Can I make a request? I need a what to wear for mom post! After I shop for our six kids I’m all shopped out. Plus I knew I was in trouble when I was shopping with my high schooler and wanted to get the same outfits and she was getting.–oops. I love having some great staple clothing items that I feel cute in, but would love some suggestions to make the shopping a bit easier. I will definitely check out the uniqlo pants you mentioned.

  12. Aw these are so fun. WOW Oscar is going to graduate this year! I’m curious which teacher he has this year! We miss our old school but Wolfie loves his new middle school. Wolfie has both of those GAP shoes too!

    And June! Baby June! In kinder?? What!

    Oh, did you know that the Zara downtown has a kid’s department? (the one on Post St!)

    Love seeing your kiddos as always! xo

  13. Does it ever overwhelm you when you suddenly realise how quickly they grow? I’m looking at June and thinking of that picture from her newborn photoshoot where she was placed on the bookshelf and I’m like… how how how????

    I was recently taking out old baby clothes for our newest little baby in the family – a little girl who my sister-in-law has adopted, and I was left wondering how those tiny clothes ever fit my kids? Were they really so small?

  14. Is Olive going to a charter school for middle school? I’ve found the past posts you did on choosing schools thoughtful, so I’d be interested to hear about this choice.

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  16. Saltwater-sandals are very proper and comfy shoes for all kids.
    Boys and girls can wear them .
    Boys like the brown or black sandals .

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