August 23, 2022

We admit it — social media is the #1 place moms and kids show off their flawless back-to-school looks.

Don’t get us wrong… we LOVE seeing what families are posting for their fall comeback! That’s why we always search for tags like #backtoschooloutfit and #OOTD (that’s “Outfit of the Day” for moms who are always looking for more hashtags)

But for fashionista parents, the absolute satisfaction comes from seeing the confidence an outfit can give to a child, especially on such an important day. Help your kids march into their classroom with pride, ready to take on any challenge that awaits!

Check out these six unique hat ideas for back-to-school that inspire positivity — and get you #trending.

1. Enter with a Smile! Colorful Smiley Hats

What better way to start the year than with a big smile?!

Children begin recognizing symbols around 18 months of age, and they are extremely receptive to positive symbols like smiley faces. Not only will a unique  smiley hat put your child in a good mood for back-to-school, but it will also elicit happy feelings in other children, encouraging a positive social environment.

Smiley hats also make for the perfect back-to-school photo! Find stylish, earthy colors that are easy to match with your little ones’ daily outfits.

For added flair, embroider your child’s name or initials on the back of their cap. Personalization shows your child how important and unique they truly are, even in a sea of peers!

2. Brother & Sister Matching Caps

Do your kids always have each others’ backs? Let other kids know who’s on whose team with BIG & LITTLE SIS & BRO  Sibling Baseball Caps!

For little ones, the first day of school can be a lot less scary when their big bro or big sis is wearing a hat that shows their love and connection. This allows them to enter the classroom with courage, even if big bro/sis isn’t there to hold their hand.

For older siblings, this sense of responsibility for their little bro or sis can help them reach new levels of confidence in their school environment, fostering leadership skills and increasing their empathy for others.

These hats are also great conversation starters with peers and teachers:

Who is your big brother or sister?

What grade are they in?

How many siblings do you have?

Once again, you’ve given your child a social advantage in their new environment!

3. Easy-to-Remember Embroidered Names

Speaking of embroidery, why not make it even easier for kids to make friends by stitching their names onto a baseball cap for the whole school to see?

Embroidered back-to-school baseball caps are a great way to introduce your child to their new classmates! This can be especially helpful for kids with hard-to-pronounce names. If other kids have ever had trouble saying your child’s name, this could be a crucial key to getting them comfortable around new people.

Hats with embroidered names are also great for telling twins apart — if they don’t switch them on you, that is! Even brothers and sisters who simply look alike might benefit from a piece of clothing that separates them from their siblings.

To top it all off, have each child pick their own color or pattern. There are so many possibilities for getting creative with custom embroidery!

4. Match The Whole Family!

The first day of school is for making a statement. You and your kids will be the talk of the drop-off line in matching baseball caps!

Show parents and students alike that your family is an unbreakable squad. Wearing matching hats as a family is a great way to give kids a sense of support, especially if they’re experiencing first-day nerves.

Plus, it looks absolutely adorable in photos! Add embroidered names or family nicknames for ultimate personalization.

Wanna expand the squad even further? Include grandparents, aunts, and other family and friends! We have hats for  Mama, Pops, Mimi, Nana, Gigi, and many more.

Both our child and adult sizes have adjustable back closures, making them an easy one-size-fits-all choice for the entire crew.

5. Spell Out Your Child’s Grade

You’ve seen photos of kids holding signs that say “The First Day of 1st Grade,” but this concept also works great for embroidered caps!

Here are some different ways to try this idea out:

Add your child’s name to the front of their cap and their grade to the back.

Put “1st-Grader” on the front of your child’s hat so they can wear their new label with pride.

Add your children’s grades to the backs of their BIG/LITTLE SIS/BRO caps.

Can you think of other ways to get creative? The canvas is yours to experiment with!

6. Bring a Matching Dolly for Support

Some kids can’t imagine going anywhere without their dolly, so why not take them to school in style? Pair one of our navy tiny doll hats with our customizable  navy baseball cap so kids can match their favorite doll or stuffed animal!

Even if their doll has to stay in the cubby during class time, your child will be happy to know a friend is close by. During the day, they can get a big hug from their dolly if class becomes overwhelming or stressful. This can be particularly helpful for kids with high anxiety.

BONUS: Pair Your Child’s Baseball Cap with Funky Striped Socks!

For a homerun look, throw in a pair of the NEW blue, pink, or tan  striped socks to be soft, durable, and ready for recess!


The most important thing to remember on your child’s first day of school is to give them love, support, and all the confidence they need to make the first day of school a total success.

Ready to get the school year started? Pick your hats, cue up your hashtags, and let’s make this school year one to remember!

Jennifer Bennett
Jennifer Bennett