Sleepy Summer may be in full swing, but the first day of school is already right around the corner. A new school year is full of new beginnings, fresh school supplies, and the perfect opportunity for your little one to express their unique personality in school-ready style.
From sending your little learner off to their first day of Pre-K to celebrating their last first day of elementary school (where did the time go?!), our Back to School Collection has something special for everyone, no matter what they’re into. We’ve rounded up our favorite looks to make getting dressed for school both fun and effortless.
First Day ‘Fits
The first day of school deserves an outfit that’s as special as the moment itself, especially when your little one is at the very beginning of their school journey.
Pre-K Precious
For the littlest of learners, comfort is key when choosing back to school clothing ideas. Our everyday essentials are designed to move with busy little bodies while looking absolutely adorable. On top of that, these styles are ideal for little ones who want to dress themselves or need a quick trip to the potty! To get them excited about their very first day of school, let them pick out a top, matching bottoms, and a hoodie for chilly mornings.
Our Play styles feel like a parent’s hug, giving them the confidence to tackle their new adventure while staying comfy all day long. We’ve made it super easy to put together their first day ‘fit with our matching set bundles. Shop the bundles to get 25% off!
Kindergarten Ready
Sending your little one off to their first day of Kindergarten? Celebrate this major milestone by dressing them in a slightly more grown-up look without sacrificing comfort or freedom of movement.
For boys, pair their favorite boys’ tee with our super-soft denim joggers. It’s the perfect balance between big kid style and all day comfort. And for girls, mix and match colorful tops and tees with soft and stretchy jeggings! Add a denim jacket or peplum hoodie for an extra cozy layer.
You can also create multiple outfit combos by choosing two or three bottoms and rotating different tops throughout the week!
For Every Little Optimist
Sunny personalities deserve kids’ dresses and outfits as cheerful as they are! Flower Power brings positive vibes and floral fun to every school day, with plenty of mix & match possibilities.
Pair the Flower Power Empire Tunic Top with Daisy Patch Leggings for a look that will add an extra dose of sunshine to their day. As the school year progresses and temperatures change, create a cozy, layered look by pairing the Flower Power Drop Shoulder Crewneck with a Soft White Puff Sleeve Tee and Light Blue Denim Jeggings.
And for boys, we love mixing and matching the Fresh Green or Jay Blue Relaxed Pocket Tee with Earl Gray Chino Shorts. These bright, cheerful boys’ tees are guaranteed mood boosters for the whole classroom.
For Every Little Creative
Let their imagination reach its full potential with Coloring Crew, the perfect print for kids who see the world as their canvas.
For your little future artist, we love the Coloring Crew Drop Shoulder Crewneck paired with girls’ denim shorts. This combo gives them freedom to create while looking effortlessly cool. And for boys, the Relaxed Pocket Tee paired with Steel Blue Chino Shorts will inspire their next masterpiece.
For Every Little Explorer
Curiosity meets comfort with our Fossil Quest and Solar Explorers prints — the perfect choices for little ones who view every day as a new discovery waiting to happen.
Dino-obsessed kiddos will love being dressed in head-to-toe prehistoric fun with the Fossil Quest Relaxed Tee and Drawstring Shorts. Recess will be filled with digging for fossils when they wear the Comet Stripes Relaxed Pocket Tee with Dry Leaf Chino Shorts.
For little explorers aiming for the stars, the Solar Explorers Relaxed Pocket Tee paired with Toasted Hazelnut Denim Joggers will fuel their dreams of outer space. Girls will love spinning around with the solar system in the Solar Explorers Skater Dress.
For Every Little Free Spirit
Royal Butterflies was made for little free spirits who march to their own beat and dance to their own rhythm.
The Royal Butterflies Flutter Twirl Dress will have them twirling all day with style, keeping them comfy while they're on the move. Cute, easy, and totally made for those "look at me" moments (without sacrificing comfort)!
For an effortlessly cool look, pair the Butterfly Graphic Double Flutter Tee with the Light Blue Wide Leg Denim Pants. It's the kind of outfit that feels laid-back but still delivers on the style points — so perfect for their day-to-day adventures.
For Every Little Prepster
Got a little learner who loves preppy style or is constantly on the move? These picks are designed for kids who love to shine and achieve.
For kiddos who strive for a perfect report card, Sweet Orchard is a must-have in their wardrobe. The Tiny Orchard Polo Shirt paired with Light Khaki Chino Shorts and an Apple Crewneck Sweatshirt for boys or the Sweet Orchard Collar Skater Dress for girls will earn them A+ grades in style.
And for those whose favorite part of the school day is PE class, mix and match their favorite Little Sleepies top with our boys’ shorts or girls’ dolphin shorts. These pieces will move with them from classroom to school gym seamlessly.
School dress code or uniform policy to follow? We’ve got you covered. Pair their favorite denim skort or denim joggers with one of our Polo Shirts or Puff Sleeve Polos to keep them comfy while looking their absolute best. Stock up on polos by bundling 3 and getting 25% off with our Back to School bundles!
No matter what their interests are, we’ve got something for everyone. From everyday essentials made to mix & match with their favorite prints, to creative and colorful collections designed specifically for the new school year.
This year, we’ve made shopping for back to school clothes easier than ever! Browse our first-ever Back to School Lookbook to find your kiddo’s perfect first day outfit in just a few clicks. Our shoppable catalog makes it simple to choose outfits that match your child’s personality while keeping comfort, style, and durability top of mind.
What’s your little one’s personality and first day ‘fit? Let us know in the comments for a chance to win a $50 Little Sleepies gift card. We pick one lucky winner every month!
