What to Wear to Middle School & High School

Earlier, I shared What to Wear to Elementary School, featuring my 5th grader and 1st grader. And now, I’m sharing What to Wear to Middle School and High School. Oscar is in 6th grade, his first year at middle school, and Olive is in 9th grade, her first year at high school.

Oscar’s school actually has a required uniform, so some of what you’re seeing in these photos are weekend clothes. But the uniform is actually pretty flexible and makes room for quite a few options. The uniform requirements are this: 1) Any khaki colored bottom (shorts, pants or skirt). In Oscar’s case, that means trousers, cords, cargo pants, and even a lined khaki “city jogger”. 2) Tops need to be either navy or white and have a collar. For Oscar, that means mostly button downs and polo shirts with long and short sleeves. 3) Top layers — like sweaters or hoodies — can be anything at all. Which makes this uniform very adaptable.

This is our first school uniform experience. So far, I like it, and I think Oscar mostly does too. Though with good grades, he can earn free-dress days on Fridays, and he thinks that’s wonderful too. Have you ever had school uniform requirements? If yes, what was your experience like?


On Olive:
Tourist tee picked up on a school trip to Washington D.C.. Pleated skirt from Uniqlo. Checkerboard slip-ons by Vans. Glasses from Warby Parker. Olive’s eyes aren’t too bad, so she only wears glasses sometimes. Instax camera here.


On Oscar:
Jeans from H&M, green t-shirt from Old Navy, jacket from Uniqlo, Converse from Nordstrom. His younger sister Betty continues to outpace him in the height department. He’s wondering if a growth spurt is ever coming his way.

On Olive:
Turtlenecklinen top and black legging pants from Uniqlo. Charcoal+black checkerboard slip-ons by Vans.

On Oscar:
Blue henley, and blue hoodie sweater from H&M. Cords from GapKids. Nike sneakers from Nordstrom.

On Olive:
Black legging pants from Uniqlo. Denim jacket from Old Navy. Vintage sweater was a gift from Maude for Christmas, picked up at a Paris thrift shop.


On Oscar:
Pull-on pants, small-print buffalo check button-down from H&M. Wind breaker from Uniqlo. Shark socks from GapKids. Denim sneakers from Target.

On Olive:
Polkadot dress from H&M. Black suede booties from Nordstrom.

On Oscar:
Volcom khakis and Converse from Nordstrom. Blue long-sleeve polo and shark socks from GapKids. Red sweater with patch elbows from Carrefore in France.

On Olive:
Black tee from Uniqlo. Green button-down jacket from Madewell via thredUp. Ripped jeans from Levi’s. Checkerboard slip-ons from Vans.

And that wraps up the school wardrobe photo shoots! Only 4 kids featured this year. So strange to think of. Our oldest two are both out of the country — Maude is spending her senior year as an au pair in Paris, and Ralph is graduated and on a mission in Colombia.

I’d love to hear: what are your kids wearing these days?

P.S. — More What to Wear posts.

14 thoughts on “What to Wear to Middle School & High School”

  1. My 9th grader daughter loves jeans and flannel shirts, and her green Doc Martens. #Seattle

    6th grade son is all jeans and tees. He likes the Cat & Jack line from Target.

  2. Anna in Stockholm NOW LONDON

    Having moved to London from Stockholm two months ago, we are now experiencing our first ever encounters with school uniforms. It is different, to say the least, but I’ve realised that I do like it. It makes sense. Boring, yes. But lovely when you think of it as a sign of equality and inclusiveness (my apologies it that is not a word). So that’s what we try to do :) The girls have ugly sweatshirts with embroidered logos, polo shirts and either skirts, dresses or trousers in grey. I feel more sorry for my son, who has to wear awful nylon shirts every day. Plus compulsory blazer, tie, trousers, sweater, book bag and “grown up” shoes… Still, all in all, I’m all for it. And yes, I do make them change as soon as they come home, to make them look like mine again… :)

  3. When we moved to England 18 months ago, we started our first school uniform experience. Uniforms here are no joke — my boys wear grey dress shorts with knee socks, a grey button down with a tie, a v-neck sweater, and a blazer. My daughter is the same but with a skirt instead of shorts. Now I am a HUGE proponent of uniforms and even like that ours our very strict and very dressy — knowing what everyone has to wear makes my life and mornings easier and the dressiness makes the kids in school take it all a bit more seriously. I didn’t know how I’d feel about it before we moved here, but now I am 100% in favor of uniforms!

    1. Anna in Stockholm NOW LONDON

      Well, hello there, fellow new Brit! Our answers are so similar, I started laughing! Hope you are enjoying the wind we’re having today… :)

  4. Thanks, I actually really needed this post! I have a 5th grade son, entering middle school next year (still waiting for a growth spurt here, too). He has absolutely zero interest in clothes, I feel out of touch with what middle school boys wear if they don’t wear all of the sporty activewear which is so popular around us. This gives me some great ideas, and this looks definitely like stuff he’d be comfortable wearing. Thanks, Blair family, and excellent modeling work!!

  5. We’ve had our first uniform experience with our older son in his public school this year: khaki, navy, or black pants (must be zip/button, no pull-on) with any color polo/collared shirt. So far we like it, although I’m quickly finding that not all pants are created equal as some of his school pairs are wearing quite a bit at the knees (a couple even have developed holes). This is not a new problem since I’ve seen it happen with his sweatpants and jeans before, but it seems so much more obvious in the dressier school pants.

    I have a hard time spending a lot on clothing I know they’ll destroy and grow out of quickly, but clearly I need to find a balance between quality and cost for these school pairs. Any tips on good quality khakis that will last and not cost a fortune?

    My younger son is still in preschool and has definite (and hilarious) opinions about what he wears. Today he chose gray thermal long underwear with a black skull print underneath neon green athletic shorts and a long sleeved TMNT t-shirt :)

  6. Olive has changed so much since she’s last been photographed on your blog. She’s wearing makeup in this shoot. I love it— she’s gorgeous. Here is Olive, now a young woman and no longer a girl.

    My favorite shots of Oscar are when he’s jumping by himself– his legs are at cool angles. These jumping photos aren’t blurry at all, and the colors are still vibrant– how did you do it?

  7. I actually love the lipstick colour Olive is wearing on her black polka dot dress – subtle yet striking. Would love to know the brand + shade, if you could share! I have a hard time deciding lip colours that will suit my very full lips, and tend to find shades seen on others online pretty helpful! Thank you.

  8. I’m in Uni now but from grade 1-12 I was at a school with a full uniform. 1-6 was at a French school and 7-12 at an all girls school. Both schools actually had different uniform items for different grades with was great because it always felt like reaching this big milestone. Personally I deeply miss my uniform because it was so easy to et ready and look put together for school, it was practically automatic so I barely even had to be awake.
    – From Canada

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