For the classroom at school to the "new" classroom at home... these playful outfits will keep your littles imagination at play!
$ 75.00
Honeycrisp: An apple for the teacher, and everyone in class! The sweet taste of Fall adorns our navy, red and yellow Honeycrisp print.
Style Description:
The WINNIE is our answer to the crisp air of New England seasons. The 3/4 length sleeve keeps little ones warm and cozy in the winter months! Pairs perfectly with ballet flats or snow boots.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature Smile Patch
Made in the USA!
$ 64.00
Our delicious red apples make for one adorable dress for a day at the orchard!
$ 75.00
autumn plaid: The colors of the harvest make for a must-have plaid! We’ve paired the multicolored print with a sparkling gold Smiling Button patch for that extra hit of cheer.
Style Description:
The WINNIE is our answer to the crisp air of New England seasons. The 3/4 length sleeve keeps little ones warm and cozy in the winter months! Pairs perfectly with ballet flats or snow boots.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature Smile Patch
Made in the USA!
$ 78.00
$ 75.00
Pink Houndstooth: We’ve updated traditional houndstooth in a soft shade of pink. A darker pink Smiling Button patch helps highlight the print.
Style Description: The DUET is the 3/4 version of our classic Double Button. It is a comfortable and versatile double-breasted dress perfect for playtime or dinnertime with the grandparents.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature smile patch
Made in the USA!
$ 75.00
Navy Houndstooth with Pink: Playful navy houndstooth gets added oomph with our light pink trim. We’ve paired it with a navy blue SB patch to keep the rest simple!
Style Description: The WINNIE is our answer to the crisp air of New England seasons. The 3/4 length sleeve keeps little ones warm and cozy in the winter months! Pairs perfectly with ballet flats or snow boots.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature smile patch
Made in the USA!
$ 75.00
School Yard Check: Sharpen those pencils and grab that textbook! Our red and blue “School Yard” check is classroom ready.
Style Description:
The WINNIE is our answer to the crisp air of New England seasons. The 3/4 length sleeve keeps little ones warm and cozy in the winter months! Pairs perfectly with ballet flats or snow boots.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature Smile Patch
Made in the USA!
$ 66.00
Flannel Buffalo Check: We’ve updated our Buffalo Check in an eye-catching blue and black. Layer it over SB leggings for an extra cozy look.
$ 66.00
Holiday Check: Looking for a holiday print? Here’s a quite literal “Check!” in festive red and green. A classic red SB patch complements the look, though we also recommend a candy cane.
Style Description: The DUET is the 3/4 version of our classic Double Button. It is a comfortable and versatile double-breasted dress perfect for playtime or dinnertime with the grandparents.
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature smile patch
Made in the USA!
$ 60.00
schoolyard check: Sharpen those pencils and grab that textbook! Our red and blue “School Yard” check is classroom ready.
Style Description:
Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
$ 60.00
Navy Hedgehog: When it comes to our animal pals, the more the merrier! Find the adorable round hedgehogs in our playful take on the classic polka dot print.
Style Description:
Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
$ 60.00
Footballs on red cord: Why can’t every day be game day? Bright red corduroy makes for a perfect backdrop to our mini footballs in this Touchdown print.
Style Description:
Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
$ 60.00
Classic Red Corduroy: Our super-soft corduroy is a perennial favorite. In Smiling Button’s vibrant Cherry Red, we’ve created an irresistible combo. Style
Description: Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
Additional Details:
100% Cotton
Machine washable
Signature smile patch
Made in the USA!
$ 60.00
pumpkin cord: Nothing says Fall quite like our Pumpkin-hued cords. We’ve paired ours with a small blue SB patch.
Style Description:
Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
$ 60.00
Holiday Check: Looking for a holiday print? Here’s a quite literal “Check!” in festive red and green. A classic red SB patch complements the look, though we also recommend a candy cane.
Style Description: Our PANT is a nod to classic American style. Much like our dresses, this little boy's pant is perfect for everyday play!
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature smile patch
Made in the USA!
$ 74.00
Spread love! A white scribble of hearts adorns this navy and white dress.
Style Description:
The SUNDAY is a darling cap sleeve dress simply perfect for dressing up or dressing down. Pair it with sneakers, mary janes, boots or ballet flats. The Sunday can be worn any day!
Additional Details:
100% Cotton
Two side pockets
Button closure
Machine washable
Signature smile patch
Made in the USA!
Monogram:
Should you choose to add a Monogram, please allow 7 Business Days for customization. All customized apparel is non-refundable.
$ 66.00
Pink Corduroy with orange bias: lightweight pink corduroy meet fall with friendly orange trim. We’ve kept the rest simple with a matching pink Smiling Button patch.
