For the classroom at school to the "new" classroom at home... these playful outfits will keep your littles imagination at play!
$ 66.00
$ 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 SB patch helps highlight the 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!
$ 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.
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!
