Kids run onto the school bus wearing their jackets and backpacks.
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Start The School Year In Style With These 20 First Day Outfits

When the outfit matches their personality, confidence soars.

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Walking into a new classroom at the start of the school year can be intimidating. But if your child is rocking the perfect outfit on the first day of school that reflects their personality, they’ll be confident and much more at ease with this new transition. And it’s not too late to grab those pieces.

When I was young I couldn’t sleep the night before school started. I was too excited. I had neatly laid out my outfits for the first few days, and had my new shoes lined up, too. These were the clothes I didn’t touch after my mom bought them because I knew they were special. In my house, we had “play clothes,” which were clothes you wore at home and had the liberty to scruff up. Then we had “school clothes.” Now of course those eventually got tired and worn and just as scruffy, but not before that first day of school.

It was always a time to shine, and there was nothing better that could boost my confidence while walking into the unknown: a new teacher, a new class, and mostly new classmates. And I’ve continued this pattern with my elementary-aged children.

Most of us buy new outfits for a new year and I’m sure you carry your own meaning and experiences behind that. And although clothes don’t make our kids who they are, they are a source of expression and creativity. When your kiddos feel comfortable and cute, that’s one more layer of self-assurance.

Here are a few outfits that you can choose for the big first day.

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Flower Print Dress

A floral print is always a happy choice for your little girl, so it’s a perfect outfit option to help her feel pretty on her first day. If she’s anything like my girls, she can’t wait to twirl in it.

Short Set

Being athletic is not a prerequisite for sporting this Puma short set. The pastel and grey camo in the shorts really compliment the pastel pink Puma on the shirt and help it pop. This will absolutely be a comfortable choice for your kid!

Zen Short Set

Step outside of the box with this tropical island-inspired short set. The split shoulder top adds some extra prissiness and the white flare shorts give it a classic linen look.

Jogger Set

Ok, sir! That will be the sentiment of watching your little boy strut into school with this black and white jogger on. I can’t promise you it will be this clean after recess, but at least he’ll start the day full of confidence and swag.

Three Colored Short Set

Did you know that SHEIN has boy’s clothing too? They are known for their unique fashion that is also affordable. This short set fits that bill and will look especially good on your little fella who has grown out of wearing clothes with characters on them.

Nike Dress

This soft-colored Nike dress is cute but is also a comfortable piece as well. It can also be nicely paired with some white Nike sneakers.

Sleeveless Animal Print Dress

Every year, I load up on these slip-on sleeveless dresses from H&M. The price is always perfect, and they have a great selection of patterns. This spotted print stands out from the typical patterns and has such a dainty look.

Dinosaur Fit

This colorful dinosaur shirt is just fun! Paired with some classic tan pants it brings even more attention to the multicolor prehistoric print. If your kid is a dino-buff he’ll be in heaven and feel totally himself as he takes on his first day.

Flare Dress

This mustard and dotted flare dress will doll up any occasion. It’s light, airy and super cute. And since it’s still pretty toasty outside, this dress still allows your girl to stay cool while she’s at school.

Multicolor Overalls

These overalls scream creativity and personality! The pastel swirls coupled with the gray shirt with pastel sleeves are a perfect first-day choice.

Dinosaur Dress

We all love cute clothes at a great price! This brightly colored dinosaur dress can easily match your girl’s brilliant personality and boost her confidence as she gets into her learning groove.


FILA isn’t a new brand, but one that is coming out with newer and cuter clothing choices. This cropped aqua top and black shorts are a vibrant and fun option for your kid's first day.

Spiderman Set

With this bundle, your boy gets to choose which Spiderman shirt he wants to show off at school. There’s no doubt he’ll feel strong wearing his favorite superhero.

Alphabet Short Set

I call this the basics because of the alphabet box on the shirt and the simplicity of this style. This fit will definitely give your kid a comfortable first day.

Striped Jumpsuit

This jumpsuit is a step up for the new year. The material is light, and the stripes are the perfect pattern to show off height. Plus, she’ll love the ruffle shoulder straps.

Gamer Graphic Tee with Shorts

If you have a gamer on your hands, get this now! But don’t be surprised if he wants to wear the shirt every day. And these denim shorts give this outfit even more character and swag. He’ll walk into the school totally confident, proudly letting his personality shine through.

Polo Dress

This pink dream reminds me of tennis attire. The cute ruffles on this polo-style dress make it extra cute for your princess and she can easily pair some sandals or sneakers with it.

Butterfly Tee Set

This beautiful oversized graphic shirt will fully represent your daughter’s love for butterflies. The colors are gentle, and the biker shorts match perfectly. She will light up the classroom!

Astronaut Tee With Jeans

If your boy likes soccer, then show him he’s the best in the galaxy with this graphic tee of an astronaut kicking a soccer ball. Paired with these distressed jeans, this fit is complete, and he’s ready to be casual cool for his first day.

Collared Shirt and Khaki shorts

There’s nothing cuter than your little man rocking his fancy button-down with some khakis. The shirt is a light material, so he’ll stay cool, but these red shorts will definitely set off his outfit. He’ll definitely be a stand-out on his first day in the class.

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