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.

August 12, 2021

By: Amanda Mushro

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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