Fun 'Fits for Your Kid's First Day of School
From preschool to high school, we’ve got first-day looks for all your kids.


Photo By: JGI/Jamie Grill
New Year, New Look!
It's time for the new school year, and kids are headed back in style! They'll have fresh haircuts, new bookbags, and outfits that are runway — or hallway — worthy. Here’s a little school style inspo for kids headed off to preschool all the way up to teens taking on high school.
Preschool: Striped Buttoned Dress
Cute, stylish, ready to play, and ready to learn. This adorable striped dress will be fun to wear in the classroom and on the playground!
BUY IT: Target, $15.00
Preschool: Blue Plaid Shirt
He’ll be a sharp-dressed little man, especially in this fun plaid shirt. Pair it with shorts or jeans and he’ll be ready to meet his teacher and new classmates.
BUY IT: The Children’s Place, $14.97
Preschool: Apple Dress
She’s already the apple of your eye and she’ll be ready to take on preschool in this adorable apple dress.
BUY IT: The Children’s Place, $6.78
Preschool: 2-Piece Set
With this two-piece set, your preschooler will have an entire outfit planned. That way, they can focus on important details — like what’s going in their lunchbox.
BUY IT: Amazon, $12.34 - $41.15
Elementary: Sparkly Dress
She’s giving off a little sparkle wherever she goes — and in this dress, that sparkle shows!
BUY IT: Target, $18.00
Elementary: Long-Sleeve Shirt Dress
She’s headed off to elementary school, but it’s not her first rodeo. This shirt dress looks stylish and cute, and so ready for school to start.
BUY IT: H&M, $24.99
Elementary: Skateboard Button-Up
This skateboard print button-up is a cool look for your big kid. With this style, we predict he’ll never be late for the school bus.
BUY IT: Target, $14.99
Elementary: Space Soccer Tee
If your kid loves science and sports, they'll love wearing this graphic tee on the first day of school.
BUY IT: Target, $5.00
Middle School: Wide-Leg Jeans
High-rise and wide legs? Hey, can we borrow these? They're made from flexible denim and feature a high, adjustable waist. Plus, the denim is made with partly recycled cotton. Pretty rad!
BUY IT: H&M, $29.99
Middle School: Comfy Joggers Set
We are digging this two-piece set! It includes a long sleeve shirt and comfy joggers. This look has comfort and style all rolled into one.
BUY IT: H&M, $24.99
Middle School: Floral Jumpsuit
We’re loving this jumpsuit moment for the first day of school. It’s fun, chic, and super comfy! With this ‘fit, your middle schooler can focus on the really important things — like getting their locker open on the first day!
BUY IT: H&M, $24.99
Middle School: Casual Skateboarding Tee
This shirt is rad and so is your middle schooler. Start the school year by showing off a casual and cool style.
BUY IT: H&M, $9.99
High School: Striped Polo & Button-Front Skirt
This button-front cord skirt and striped top is giving us major ‘90s flashbacks and we love it. Pair this ‘fit with white sneakers to start school on the right foot.
BUY IT: Target, $12.00 (Shirt)
BUY IT: Target, $17.00 (Skirt)
High School: Tropical Short Sleeve Button-Up
Summer might be coming to a close, but this tropical button-up shirt will look great paired with a graphic tee and jeans for all four seasons. Snag this shirt for your high schooler's first day.
BUY IT: American Eagle, $39.95
High School: Jean Jumpsuit
Will this be the best school year ever? We don’t know, but with this first day of school look, it’s already off to a great start.
BUY IT: Old Navy, $49.99
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