The holiday season is filled with magical moments and special traditions — from getting the entire family together for dinner, to exciting activities like seeing The Nutcracker. Dressing them for these festive occasions should be just as joyful and easy. That's where Little Sleepies comes in!
Our Holiday Play Collection is designed to keep your kiddos cozy and cute, no matter the event. Whether it's a school holiday party, a family dinner, or a matchy movie night at home, we've got adorable and picture-perfect outfits for every occasion.
Get ready to make this holiday season extra special with looks that blend next-level comfort, cute style, and festive cheer!
For the School Holiday Party
'Tis the season for holiday parties! Whether they're playing Santa Says or Pin the Heart on the Grinch, our Holiday Play collection has your little ones covered in soft, snuggly style.
Bring the holiday cheer to the classroom with the Holiday Red Ribbed Tiered Peplum Top. Pair it with the Snowy Blooms Legging and Midwash Blue Denim Trucker Jacket and they'll be running around with Christmas cheer from drop-off to pick-up!
For an outfit as cool as those winter temps, look no further than the Cool Christmas Pocket Tee or Bodysuit. Layer it with the Rockin' Around Crewneck Sweatshirt and Denim Joggers for a cozy-cool vibe that will keep up with your kiddo long after the sugar rush wears off.
For a Picture-Perfect Family Dinner
It wouldn't be Christmas without a home-cooked meal with family, complete with a fresh-baked pie! Keep your little ones comfy—and looking their best—with these Holiday Play faves.
Create sweet sibling matching moments at dinner with the Fireside Plaid Smocked Dress (add tights for extra warmth) and Evergreen Plaid Polo Romper or Button Down Shirt with Black Denim Joggers. When the celebrations move outside for s'mores, layer on a Black Zip Hoodie to keep them toasty.
If your family's all about a more laid-back vibe, the Holiday Checks Crewneck with Caramel Jogger and Holiday Checks Skater Dress are perfect for keeping it cute and comfy. Don't forget to add the Caramel Checks Sherpa Bucket Hat for the cutest (and softest) finishing touch! When it's time to wind down after dessert, one of our favorite choices for holiday family matching in trendy neutral colors is the Modern & Merry Collection!
For Christmas Caroling
You've been singing and dancing along to a festive holiday playlist since the weather finally dropped below 60º. Now, it's time to spread the Christmas cheer in your neighborhood by going caroling!
Going caroling calls for outfits that are both practical and comfortable. Your littles will be singing their hearts out in this Tree Traffic Crewneck and Olive Denim Jogger. Add a Bodysuit or Relaxed Pocket Tee underneath for an extra layer of warmth if you're going in the evening.
For daytime caroling, the Golden Blooms Tiered Peplum Top with its gold metallic foil details will shine as bright as your kiddo's holiday cheer. Pair it with the Midwash Blue Denim Jegging for a casual and cozy look! And for your little drummer boy, we love the Tree Traffic Bodysuit paired with our Toasted Hazelnut Denim Jogger!
For Festive Evening Activities
If seeing The Nutcracker or going to an evening service is part of your holiday plans, you'll want to have your little ones looking sharp while staying comfy. Here are some of our fave Holiday Play styles for your festive evening activities this holiday season.
Have a mini ballerina in the family? The Golden Blooms Tiered Tutu Dress or Snowflake Tiered Tutu Dress will have them ready to twirl the night away in snuggly comfort. Add a pair of tights for extra style and warmth.
Our Cool Christmas Polo Romper or Button Down Shirt paired with a Denim Jogger will have your little one looking as dapper as ever. Add on the Heather Gray Stripes Zip Sweater for another layer of soft comfort. And for a picture-perfect sibling matching moment, pair it with the Holiday Red Collar Pocket Dress.
For a Charitable Holiday Outing
One of the most memorable and magical things you can do with your family during the holidays is giving back to your community. Whether you're going shopping for Angel Tree or USPS Operation Santa presents or volunteering at your local Feeding America, these Holiday Play styles will keep your little ones comfy while giving back to those in need.
Spark some joy as you shop with the Cheer Drop Shoulder Sweater. We love it paired with Midwash Blue Denim Jeggings for cozy comfort from head to toe. Our Rockin' Around and Tree Traffic Crewnecks are great options as well! Paired with your favorite joggers, your little one can move with easy as they help serve meals.
As the holidays fill your home with laughter, love, and sweet treats, dressing your littles in outfits that bring comfort and joy makes every moment even more special! Our Holiday Play Collection has the perfect look for every memory you'll create together. No matter what festive fun is on the agenda, we're here to keep your kiddos cozy and cute!
We'd love to hear from you!
Drop your own outfit ideas
or holiday traditions below
for a chance to win a
$50 Little Sleepies gift card.
We pick one lucky commenter
every month!
