Step 1: Build Up to a Great Start

Boxes of crayons, miles of pencils, school books, and aisles of backpacks—nothing says Autumn quite like the start of the school year. If you have a little one in the house and they’ve reached the age for preschool, preparing them for their first day be a mixed bag of emotions—awe at how fast they’ve grown, heartbreak for missed baby snuggles, and worry about sending them off with all the right materials and cute back to school clothes.


Fortunately, prior to the first red leaf falling or the first yellow bus trundling down your street, there are some steps you can take to help ensure that your little scholar gets off to a good start. From the ABCs to the 123s, from backpacks to bedrolls and toddler boy clothes, this guide has everything you need to know to prepare them for a great first day of preschool.


Step 1: Build Up to a Great Start

The first day of preschool is a huge event—both for you and your child. Starting preschool is the first step into the long years of education. However, you can take some of the jitters out of the buildup by taking time with your preschooler-to-be to prepare for what’s ahead. Some great ways to make a great start are:


  • Play preschool – In the week leading up to the beginning of school, do a little roleplaying with your child. Make a little classroom in your living room and let them play school. You can be the teacher, but also allow them to be the teacher. Involve favorite toys or dolls in the classroom for extra fun. Keep the game silly and simple but try setting common rules like:
    • Take turns
    • Don’t talk when someone else is talking
    • Share nicely
    • Treat your books and supplies well


  • Talk about it – Address any worries your child may have about their first day away. Tell them about your first day at school or watch a movie or a TV show about how to handle classroom rules, meet new friends, and listen to the teacher. 


  • Visit – If you can, visit their future classroom when it’s quiet. Let them meet their teacher and look around. Also, be sure to visit the playground and any common areas like a lunchroom or art room. 


  • Celebrate the event – As the day approaches, talk about how you will celebrate. Will you have a special breakfast or dinner that day? Maybe a favorite treat will be in their lunchbox. You can even find back-to-school gifts for students to encourage them on the first school day. Overall, make the day feel like an exciting activity that they’re so lucky to be a part of—because they are! New toys, friends, and learning opportunities abound!


Step 2: Gather Supplies and Essentials

School readiness can also help ease off the jitters for every young child and parent. Most schools will have a list of supplies and essentials that your preschooler is expected to bring on the first day. While these will vary from school to school and region to region, some basics that you may need to purchase for your child’s first day of preschool success are:


  • Size-appropriate backpack
  • Lunchbox and accompanying food containers
  • Water bottle
  • Spare clothes, including underclothes in case of spills or accidents
  • Bedrolls or sleeping pads for nap time


If you know your child will be participating in coloring, reading, or writing activities, take them out on a mommy-and-me day to pick out all their favorite supplies—from crayon packs with all the colors of the rainbow to folders and notebooks with their favorite cartoon characters. 


It’s a good idea to label everything your child takes to school. Many a jacket or hat has disappeared forever into the lost-and-found for want of a label. You can get super-sticky plastic or vinyl name labels pre-printed with your child’s name, use fancy embroidered labels, or write it on with a waterproof marker.


Step 3: Find the Perfect First-Day ‘Fit

Once your little one is equipped with the emotional and physical tools to make their first day a fabulous one, it’s time to find the perfect outfit for the big day. Your little girl’s first day of preschool can involve a gambit of activities—sing-song get-to-know-you circles, indoor and outdoor play, the ABCs, the 123s, and perhaps even a few arts and crafts. 


So, you’ll want to build an outfit that’s just as versatile. Our RuffleButt collection is made with joyful, comfortable experiences in mind:


  • Luminous Loungewear – Pastel never looked so pretty. Match your little girls’ favorite crayon sets with this rainbow lounge set, complete with a long-sleeve top and comfortable cotton shorts. It’s the perfect pick if you’re expecting sunny skies, a light breeze, and a day of sitting criss-cross-applesauce and making new friends on the playground; $30. 


  • Floral ‘Fits – For warmer first days, this two-piece turquoise-blue lounge set makes the perfect splash. The best part? It has pockets. From crayons to rocks to little crumpled-up balls of paper on the floor, they can store all their favorite trinkets while on the go. This short sleeve and short is also made with high-quality soft fabric so your little one can stay cozy from drop-off to pick-up; $30.


  • Effortless Dress – Showcase your little girl’s sunshine with this smock-styled butterfly sleeve dress. It’s easy to slip on amidst first-day scrambles to the door and is casual enough to fit right in on the playground—just pair it with playground shorts and you’ve got an outfit that’s both fabulous and functional; $30; $20. 


  • Magical Blouse – Set your preschooler up to make waves on her first day with this signature mermaid tee. It’s stylish, comfortable, and likely to lure in plenty of new friends. Pair it with shorts, a skirt, or a pair of loose-fitting pants for a magical first day worth writing stories about; $20.


  • Basic But Beautiful Tee – Available in a variety of prints, from Flower Patch to Dolphin Blue, this knit-fabric top is the perfect go-to if your preschooler is expecting to spend their day playing outside. Plus, the variety of colors means it can easily become a wardrobe staple. And there’s a keyhole opening in the back, making for easy changing; $23.


  • Joyful Joggers – For a put-together yet casual outfit, fit your little one in these comfortable denim joggers. No matter what top you pair them with, she’ll be ready to take on the day—she’ll be able to run, hop, color, and sit in complete comfort; $17.99.


  • Free-Spirited Shirt –  Your boho honey will look absolutely scrumptious in this ruffled long-sleeve tee. The layered look adds a dynamic feel and will keep her warm when the air conditioner kicks on, too!; $15.99.


  • Prim and Pocket Dress – Show off your little girl’s personality with this striped pocket dress. Its ruffled, functional pockets can hold granola bars or secret love notes you sneak in before your first-day goodbye. It’s lightweight and loose, too, for easy all-day play; $16.99.


  • A Bow on Top – The colors of the rainbow aren’t limited to crayon boxes and colored pencil collections—this elastic washable head bow comes in various shades of ROYGBIV to complete any first-out outfit with a touch of cute. Plus, it can easily keep your little girl’s hair out of her eyes while you’re not there to do it for her; $10.


How to Prepare for Mom’s First Day of Preschool

Let’s be honest, the first day of preschool might actually be harder on you than on your little student. It can be very difficult (very very very difficult) to say goodbye to your sweet child on their first day of preschool. This is entirely appropriate and a sign of love and good parenting. Take pride in that. 


For a sunny disposition, even on the toughest of days, we’ve compiled a few ways to cope with the rollercoaster of first-day feelings:


  • Share your feelings with a friend or family member
  • Write in a journal about the day
  • Take a long walk or spend time in nature
  • Know that you are not alone and these feelings will pass
  • Look forward to the moment when you get to snuggle with your precious little girl again and hear about all her stories from the day


Preschool Pretty with RuffleButts

The first school day for toddlers can take a lot of preparation and time, maybe even the second day or the whole first week—for both you and your child. But, dressing your preschooler in the morning doesn’t have to. 


At RuffleButts, we’ve got everything you need to effortlessly dress your little scholar for success on her first day of preschool. Whether you’re opting for boho chic or comfortable and casual, we’ve got a toddler button down shirt, legging, tee, tank, or dress to match. 


No matter what you choose, she’ll be looking A+ for her first day of preschool in a RuffleButts outfit. And best of all, you get to skip the back-to-school shopping lines and have it all delivered directly to your door. Shop our collection today.




Huffington Post. Parents Share How Hard It Is When Your Child Goes to School for the First Time.


California Department of Education. California Preschool Curriculum.

National Association for the Education of Young Children. What Do Children Learn in a High Quality Preschool Program?