What to Wear to Middle School and Preschool

Olive & June Outfit17What to Wear to Middle School and Pre-School  |  Design Mom

Photos and text by Gabrielle.

Here is the third and final installment of our 2013 What to Wear to School posts, featuring the lovely Olive & June. This is  a bit of a landmark post, because it’s the first year that June has had interest in participating. And boy was she interested! She thought the whole experience was pretty much the funnest thing ever and kept bringing me additional pieces of clothing that she felt should be included — Mom?! What about my watermelon pajamas? Mom! My slippy slops!! (Which is how she pronounces ‘flip flops’.)

Olive has had a big growth spurt since last year and her wardrobe is pretty much entirely new. In contrast with June, who is mostly wearing clothes we bought in France last fall/winter (most are from our favorite French grocery store), sprinkled with hand-me-downs. I confess, I will be sad to retire her little clothes. But on the bright side, it was so fun to have her join in the fun this year.

I hope you enjoy the tour!

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On Olive:
Houndstooth Dress from Gapkids (sold out online, but the polka dot version is cute too!). Yellow Knit Tights from H&M. Leather Ballet Flats are hand-me-downs from Maude, purchased at Carrefore, a French grocery store.

On June:
Floral Scarf from Zara Kids, Striped Dress and Grey Knit Tights from Carrefore, Leather Boots are hand-me-downs from Betty. And Betty wore them as hand-me-downs from our friend Kathryn (I don’t know the brand, but you can find similar here.)

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On June:
Smiley Face Hoodie, Blue Heart-Pocket Dress, Knee-Patch Tights from Polarn O. Pyret. Booties from Carrefore.

On Olive:
Polkadot Dress, Navy Cardigan, Pink Knee Socks from Polarn O. Pyret. Chambray Dot Sneakers by Vans.

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On Olive:
Teal Denim and Neon Striped Tee by GapKids. Grey Fleece Moto Jacket by Old Navy. Chambray Dot Sneakers by Vans.

On June:
Ruffle Collar Top and Denim Skirt by ToobyDoo (hand-me-downs from Betty). Sweater & Booties from Carrefore. Socks by BabyGap (hand-me-downs from Oscar).

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On June:
Apple Pocket Dress by DPAM. Navy Tee and Navy Shorts by Generation Z. Grey Socks and Leather Booties from Carrefore.

On Olive:
Navy Tunic and Printed Jeggings by Old Navy. Asymmetrical Vest by H&M. Canvas Sneakers by Puma (hand-me-downs from Ralph).

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On Olive:
Yellow Tennis Skirt by DPAM. Navy Knit Blouse by H&M Kids. Chambray Button-Up by Old Navy. Sneaks listed above.

On June:
Yellow Gingham Top and Red Anchor Sneakers from Carrefore. Denim by Generation Z. Tiger from Pottery Barn Kids.

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On June:
Pink Blouse and Grey Corduroy Jumper and Pink Knit Tights from Carrefore. Boots are listed above.

On Olive:
Navy Print Dress and Grey Cardigan from Sergent Major. Pink Leather Ballet Flats from Carrefore.

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And that’s a wrap! Now I’d love to hear what you think. Would your kids wear any of these outfits? Is Olive still channeling a French influence, or is her wardrobe looking très Américain? Does your 3 year old dress like June?

I sincerely hope you’ve enjoyed this year’s wardrobe tours. If you’d like to see more, you can find all the What to Wear to School posts here. Hooray for Back to School!

41 thoughts on “What to Wear to Middle School and Preschool”

  1. The girls look adorable! I think their outfit choices are so playful and wonderfully, age-appropriate. June has so much style and at the same time, looks ready to hit the sandpit. Olive is lovely and so chic! I can definitely see the French influences – casual, fun but with flair. Wishing the Blair kids a great school year!

  2. just saw the time of my comment sending…I’m in England and enjoying blog reading while kids are at school and am NOT up all night! Ha!

  3. Olive – you’re a natural! Quite a beauty! All of your outfits are fabulous.

    And I adore Betty’s curls and all those ruffles around the neck. Cute, cute, cute!!!

  4. If you could give me any tips on making sure that scarf comes back home with them I’d be eternally grateful.

    Also applicable to cardigans, of which we’ve inadvertently donated 8 to other children at school over the past year alone.

    1. Ha ha, too true. Maybe it gets better when they get older, but last week my 5 year old lost 5 things over three days (a cardigan, a hoodie, ballet shoes, a ballet leotard, and a teddy bear). All of them are clearly labeled with her name, too (I learned that lesson the hard way)! Luckily, I was able to recover 4 out of the 5 items through various lost and founds and other children bringing back her items they accidentally took home, but we did have to buy her a new leotard. We had a serious talk about it, but these weren’t the first items lost, and I’m sure they won’t be the last. I actually thought of Gabi’s comments previously on the blog that her kids don’t have many more outfits for the year than the ones shown here–I’m so envious (it would allow me to pare down, and focus on quality over quantity), but I don’t think we could do that. Between losses and irreparable stains, my kids do end up really using 10-15+ tops, bottoms, dresses, etc. each year.

  5. I loved EVERY outfit. My favorite thing about all three WTW posts is that your kids look age appropriate! And prove that you can look great while doing it! :) Fun posts.

  6. Oh my word — those girls are so adorable! LOVE their outfits! Will be copying for off-school wear as my girl wears a uniform. Such pretty girls you have — love their curly hair!

  7. Beautiful girls and adorable outfits. I must acquire one of those houndstooth dresses for my older daughter. My husband would love it since he’s a big Alabama Crimson Tide fan!

  8. Absolutely darling! I love seeing the girls together. They look wonderful!
    I love their style.

    I marvel at your children’s willingness to pose for photos. Tips on THAT, please! Mine are only 1 and 2 so perhaps they will improve with time.

  9. I’m amazed that Olive will wear dresses. My daughter (who’s the same age) theoretically likes them, but she’s nervous to wear them to school (mostly because of comments she thinks/knows her friends will make). Does Olive wear them to school?

  10. Your daughters are both beautiful!

    Can I say, the thing I’m most jealous of is your 3 year olds enthusiasm for those beautiful clothes. Getting dressed in a major point of contention with my 3 year old. No skirts, no jeans, no 3/4 length shirts or capri pants, no sneakers, no flip flops. The list goes on and on! I’m starting to panic a little since it’s getting cold and we fight about leggings everyday. I wish June could call her up and explain the wonders of cute clothes.

  11. June is soooo cute! Olive looks so tall and grown up! I love all of their outfits. I swear you have the most stylish kids in the universe. Olive looks tres chic to me (very French) and that’s a good thing!

  12. I loved this “What to Wear” post! I think my favorite thing is that you aren’t afraid to incorporate hand-me-downs, and from both genders, into these darling outfits. I’d love to hear how your family manages the hand-me-downs. You know, the nitty-gritty of sorting and storing, and figuring out what is worth the effort and storage space.

  13. How interesting! I love the way the girls dress! Very chic. It is interesting that other 3 year olds are getting more involved in their wardrobe like my daughter. She just turned 3 and over the last month has become very involved (and picky) about what she wears!

  14. LOVE their outfits!! Gives me great inspiration for how to dress my little girl. And could Olive please teach me how she does her hair? My hair is very similar to hers, but hers is styled far better than mine . . . :) Beautiful girls!

  15. I LOVE Olive’s style – I’d seriously love some of those outfits for myself! (and I’m long out of middle school!) Both girls look so happy and stylish and radiant.

    I second the request above re: managing/storing hand me downs!

  16. What lovely girls! As with the other installments I’m most taken with the denim outfits with funky/unexpected touches. That denim skirt on June is beyond adorable. And I LOVE both girls’ hair. While very different in color and texture both wear their hair in a way that brings out the natural beauty of healthy, growing, glowing girls

  17. I’m wondering if you’ve ever done a post about curly hair, seeing as you and several of your kids have quite curly hair…if you haven’t, would you consider it? I imagine you’ve got a couple tricks up your sleeve! My three year old has hair just like June’s, and while I can manage to get it under control when need be, it is a bear to tackle on most days.

  18. Ah, seeing June made me miss dressing a little, little girl. They have the cutest clothes and everything just looks so darn precious! Our girl is sprouting up too & I feel like every time she comes home from school she looks older. Everyone could use a tiny little girl in their world. :)

  19. Gabi, I would love to see a post on how to put together outfits for kids the way you do. I like that their outfits are a stylish twist on classic, and still very personal to each child. Do you start each outfit with an inspiration piece? How do you budget each piece-decide what to spend on, what to save on? We tend to have way too many wardrobe options in our home and it is more work on all of us.

    Also, many have mentioned they would wear these outfits in adult versions. How about a What Gabrielle Wore post?

  20. I love these posts so much! Baby June is, of course, sooo adorable! (Wolfie had the same crazy blonde curls at that age, so she always makes me smile!) And then Olive…what a poised and chic girlie! I especially like the combination of styles. The houndstooth dress is SO stylish and makes her look like such a little lady…..but then she’s also rockin’ those Old Navy leggings. It all feels very appropriate and stylish. Loving the Blairs in Oakland!

  21. Gabrielle, yellow tights look just awesome. They bring so much energy and brightness to Olive’s image. She also looks very pretty in her Navy dress. As for June, I appreciate her first image with red patterned scarf. Have you ever tried green color and all its variations? I believe girls would be very pretty little ladies in those.

  22. I don’t even have school age kids anymore and, still, I love these posts. I look forward to them each year :) Your children’s personalities really seem to come out in the pictures. But that June! Oh my. that Sweet face and curls – deadly combination – personality plus! Thanks so much.

  23. Gabrielle, I don’t think I ever told you that my grandmother’s name is June and her sister was Olive. They had another sister named Fern! I love all the names in your family.

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