cool school stuff

What 25 Students From Preschool to Grad School Are Wearing on Their First Day Back

As days get shorter and temperatures cool, it’s also time (eek) to start thinking about going back to school. To help you get a jump on the best school (and school-related) supplies to buy for fall, we’re running a series called Cool School Stuff, in which we’ll sniff out the best backpacksbest dorm décor, and best bento boxes, among many, many other things.

We all know that whatever anyone wears to the first day of school is the most important thing they’ll wear all year. It defines how you’ve matured and changed over the summer, while setting the tone for the rest of the year. So if just thinking about it is getting you all flustered, we’ve gathered some inspiration below.


“This outfit is so pretty because it has twinkly stars all around! I like that these shoes are sparkly and shiny. I like my hair down with this bow to show my curls. My favorite superhero is Wonder Woman, that’s why I like this backpack.” — Ruby, preschool

Grade School

“I like this one long dress that has a lot of details. I like that it feels very comfortable and how it’s long, so I don’t have to wear shorts underneath.” — Riley Han, kindergarten

“I want to dress up because it’s first grade. I’ll wear a pink dress with bananas, a bird, a peacock, watermelon, and flamingos on it. I’ll wear a headband with cat ears that are pink with glitter. I would also wear gold sandals.” — Cassia Larren, first grade

“I have one shirt that I usually wear for special things, so I’ll probably wear it for my first day of school. It looks like a soccer shirt.” — Rowan Han, first grade

“I like my backpack because of the bow. I like my shirt with the sparkles. I can’t wait to wear them together.” — Zara, first grade

“I feel like my dad in this button-down shirt.” — Hayden Bick, second grade

“I really like wearing suits, and I like the pattern on this one. I also like the fact that it comes with a vest. I might wear patterned pants, too. I have a game called Qixel, and I’m obsessed with making patterns on it, so that’s what I love to wear, too. My dad got me these new shoes, and all I have to do is hit a button and they light up and make all different color patterns, but they’re a pain to put on. I still wear them, though. I also have a watch that I wear every day, except for when I’m in the sandbox. It’s a blue Swatch and I just got the battery repaired, so now it glows.” — John Savin Nguyen, third grade

“I can’t wait to wear my outfit and backpack. They look so pretty. There’s a bow and pink polka dots on the backpack. My pants have pink butterflies, and the flowers on the pants are fabulous because they’re better than I can draw. The shirt has items that I like: the Eiffel Tower, Minnie Mouse, a shirt, sunglasses, camera. All Paris stuff.” — Ameera, third grade

“I went to try on new clothes and I liked these jeans and this shirt. I like how the top and the jeans go together, and how it all makes me look older.” — Bailey Han, fourth grade

“I want to make a good first impression that I’m cool, I guess, because I’m going to a new school. I have this cool hoodie from Laguna Beach that I got this summer because they have cool surfer shops there. Most of my clothes are skateboarder stuff. I got new Nike’s that are for skateboarding, too. They’re black-and-white high-tops. I’d just wear regular shorts like Adidas or something. If it gets hot, I’ll roll up the sleeves on the hoodie.” — Ben Dallal, sixth grade