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.


Girls’ Shooting Star Graphic T-shirt

“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

Skechers Girls’ Twinkle Toes Shuffles Buzzing Blossom High Top
Organic Linen Mustard Clip
DC Comics Wonder Woman Backpack With Detachable Cape and Side Mesh Pockets

Grade School

Wagga Wagga Wrap Neck Sundress

“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

Patterned Jersey Dress

“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

Bonnie Z. Leonardo Girls Super Cute Glitter Cat Ears Headband
Salt Water Sandal
Adidas Youth Soccer Estro Jersey

“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

Loungefly Hello Kitty Rainbow Tie Dye Backpack

“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

Embellished Ruffle Short Sleeve Tee
Plaid Flannel Long Sleeve Shirt

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

Navy & White Houndstooth Blazer

“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

Kids’ Short-Sleeve Secret Wash Shirt in Neon Gingham
Fairmount — Black Licorice
Hello Kitty Black and Pink Polka Dots Backpack With Ears and 3-D Bow

“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

GapFit Kids Graphic Sport Leggings
Asymmetrical Pleat-Hem Tank

“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

High Stretch Side Embroidery Skimmer Jeggings
Nike Blazer Mid

“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

Adidas Originals Superstar Shorts
Laguna Beach California Hooded Sweatshirt
SkinnyShirt Women’s Seamless Tank

“I’m starting eighth grade, but in Chapin, where I go to school, that’s starting high school, so this is the first year I don’t have a set uniform. We can choose our own shirt as long as it’s collared and in green, blue, or white. I’m planning on wearing a dark-blue polo shirt from Lands’ End with a SkinnyShirt underneath. The SkinnyShirt helps so that the polo shirt doesn’t bunch up or look wrinkly. It just fits really well. For my shoes, I’m planning on wearing cute little tennis shoes I got from Bloomingdale’s, something like Stan Smiths.” —Kailey Perkins, eighth grade

Women’s Pique Polo Shirt
Women’s Stan Smith Lace Up Sneakers
Free City We Are Everything Short Sleeve T-shirt

“I haven’t gotten my outfit yet, but I’d probably wear a Free City or Brandy Melville T-shirt because they’re really cool and comfortable. I go to a private yeshiva, so I’d wear a Hard Tail skirt. My shoes will probably be Jack Purcells or Superstars, depending on which I like better that morning.” — Rebecca Altholz, ninth grade

Hard Tail Skinny Knee Pencil Skirt
‘Dry Out’ Dri-FIT Chino Shorts

“I’ll probably wear khaki shorts, a blue polo, and my Rod Lavers.” — Jason Sarachek, tenth grade

Polo Ralph Lauren Weathered Mesh Classic Fit Polo Shirt
Rod Laver Super Sneaker
Gucci Princetown Horsebit-Detailed Leather Slippers

“I’m wearing my uniform plaid skirt with cute Gucci slippers, a cute vintage Levi’s tee that says little devil on the front, and a black leather jacket from Iro that’s stretched leather. I’m also going to wear a simple monogrammed necklace.” — Jillian Schwartz, 11th grade

Re/Done Little Devil Graphic Tee
Iro Ashville Leather Moto Jacket
Flounced Skirt

“I’ll probably wear a black, flowy skirt from H&M and a striped T-shirt from Brandy Melville. That’s pretty much what I wear every day, but the T-shirt is new. I’ll wear it with Velcro Stan Smith’s. A lot of people are still wearing those, but I think the trend is fading.” — Leila Deluty, 11th grade

Adidas Men’s Stan Smith CF Originals Casual Shoe
Slim Low Jeans

“I go to school abroad and I live in a dorm, so we’ve all kind of passed the stage of caring. I really haven’t planned what I’m going to wear, but I’ll probably throw on a T-shirt and jeans from H&M.” — Mo Weiss, 12th grade

3-Pack T-shirts Regular Fit
ASOS Midi Skater Skirt in Jersey

“A black, flowy skirt, probably one that I have from American Apparel, a tight, short-sleeve T-shirt, and black ankle socks with black low-top Vans with laces.” — Deborah Greenfield, 12th grade

Calvin Klein Jeans Rib-Knit Baby Tee
Hanes Women’s ComfortBlend No Show Pack of 6
Vans ‘Authentic’ Sneaker


Sam Edelman Women’s Kavi Sneaker

“For my first day back on campus, I’ve been dreaming up an all-white outfit: jeans from J Brand, which is my favorite (but Topshop is a more affordable option, especially with the extra student discount), a T-shirt from J.Crew, and new sneakers I just got from Sam Edelman, with a plaid button-down either left opened or tied around my waste. Why white? Because its clean, fresh, trendy, proof that one can wear the color after Labor Day (gasp!), and lets me live in a world where summer lasts all year long. The plaid gives the look some color, provides a layer of comfort, and most importantly, ensures that I don’t look like I am trying too hard.” — Raquel Greenfield, college sophomore

J Brand 811 Mid Rise Skinny Jeans
Vintage Cotton Scoopneck T-shirt
Plaid Drapey Shirt
Cinch Waist Mini Dress

“When I put on this dress, I feel like it’s an instant outfit. The print, along with the silhouette, makes me feel like Dorothy from Wizard of Oz, but Auntie Em is DVF.” — Julia Sinski, college junior

Block Heel Mules
Sissy Boys Unite Tee

“The tee is because that same artist did my Daddy Trouble tee, which is one of my favorite things I own. The pants because I like the cut of the pockets and the short ankle. I’m super tall, so my ankles need to breathe. For the tote, initials are cool, but saying something trendy and kind of questionable is cool, too. Something like ‘Pow’ or ‘Oops.’ These Prada sandals because they’re over half-off and will go with anything I dare wear them with. And I’ll top it off with a Comme’s Fragrance because it smells like an old church that still burns incense.” —Jack Oberle, college junior

Cotton Twill Chinos
Boat and Tote, Open-Top
Prada Runway Cage Sandals
Comme des Garçons Parfum Palisander Perf
Opening Ceremony Gel Box Logo Tee

“This whole outfit would probably be accessorized with some thrift dangly gold earrings and a colorful belt from American Apparel, in something like purple or red.” — Alison Maybaum, college junior

BDG Girlfriend High-rise Jean — Light Wash
Vans Classic Checkerboard Slip-on Sneaker
Jennifer Fisher Knot Choker

“Jennifer Fisher is literally #goals, and her necklace brings every outfit of mine to another level, so how can I not wear it on my first day?! I hate to come off like a basic white girl, but honestly, this Brandy Melville shirt is amazing and goes with everything, and it’s the perfect way to be casual, comfortable, and stylish. I usually like to wear shorts in the summer, but there is something about the first day that I just want to look more mature after I haven’t seen most of these people in a while. I also want to be a bit more modest, especially because I don’t know what my teachers are going to be like. Anyway, this is the perfect pair of jeans to show people you still have style. Lastly, I love loafers, and I wouldn’t go anywhere without my boy brow.” — Julie Schwartzberg, college junior

Le Crop Bell Jeans
Coach Lenox Loafer
No Name 40 mm Plato Canvas Platform Sneakers

“These are the perfect white platform sneakers that I’ll pair with a casual but interesting pair of jeans, a cool graphic tee that tells people I went abroad and changed, and a sweater because schools crank up the AC, and also because it’s the coolest thing I wish I bought when I was abroad. I don’t need a bag because nobody uses notebooks anymore, but I love this laptop sleeve, and I’ll fill this bottle with water during the day and wine for a night class.” — Sabrina Kogut, college senior

Slim High Waist Jeans in Samurai Blue
Givenchy Antigona Rottweiler Art Print Laptop Sleeve
Whitney Travel Bottle 26 oz

Graduate School

Maude Mid-Rise Cigarette in Shadow Black

“On my first day of school, I would potentially wear: my black J Brand jeans, striped T-shirt from & Other Stories, and either Superga’s or flat black sandals. As a grad student, I’m going to push myself to try to not wear leggings to class.” — Sophie Jenkins, graduate student studying art history and artist administration and policy

Round Neck T-shirt
Superga ‘Cotu’ Sneaker
Blundstone BL584

“I’ll be starting a graduate program where everyone will be older, more experienced, and most likely more talented than I am, so all I have is that I’m youngish and theoretically cool. My first-day-of-school outfit will try to reflect that. Something that says, “I’m not trying too hard, but I am the same age as your children, and if we knew each other, they’d be intimidated by me.” That’ll probably be my Blundstone’s, skinny jeans and a vintage tee.” — Jonny Gottlieb, graduate student studying nonfiction creative writing

Cheap Monday Jeans Tight Skinny Fit in New Black
Vintage ’90s Vertical Stripe Short Sleeve Button-down Shirt

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25 Students on Their ‘First Day of School’ Outfits