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.