Boden Woven Smock Top
This smocked top, with details like embroidery, pintucks, and delicate frills can make even the most casual leggings-and-sneaker combo look put together. Ultra-soft twill means supreme comfort. Also available in a turquoise squirrel print.
To buy: $39, bodenusa.com.
STATE Bags “Kane” Backpack
This sturdy, kid-sized backpack is full of interior organizing pockets (including a padded one for tech items) so nothing gets lost. A serious bonus? State’s “Give.Back.Pack” program ensures that for each “Kane” style sold, they’ll donate and deliver a backpack full of school supplies to an American child who needs one.
To buy: $60, nordstrom.com.
The Children’s Place Girls Glitter Bow Audrey Ballet Flat
Pretty enough to be party shoes, these sparkly ballet flats have a sturdy rubber sole and flexible construction to dress up everyday outfits, too. Also available in burgundy.
To buy: $25, childrensplace.com.
H&M Boys Long-Sleeved T-Shirt
A fresh, graphic take on classic Breton stripes, this cool tee is fit for school and play. Available in five prints.
To buy: $10, hm.com.
Zara Girls Cardigan With Fur-Lined Collar
As pretty as it is practical, this sweet sweater’s faux-fur collar is removable for a more laid-back vibe before the weather gets cool. Go-with-anything grey looks great with everything from jeans to girly dresses.
To buy: $40, zara.com.
Osh Kosh B’gosh Embroidered Boho Dress
Cheerfully bright and full of details like metallic thread and contrasting embroidery, this little shift is surprisingly seasonless. Pair it with sandals while the weather is still summery, or add light-colored tights and a sweater to layer against a chill.
To buy: $20, oshkosh.com.
Old Navy Patch Jeggings For Girls
Stylish enough to give even grown-ups a little wardrobe envy, these kid-sized jeans are full of stretch, so they’ll be just as comfy as her favorite leggings.
To buy: $17, oldnavy.com.
Converse Chuck Taylor All Star Street Leather
The cool-kid classics look even—well—cooler when done in leather.
To buy: $52, nike.com.
River Island Boys Black Demi Boots
Toe the line between formal and casual with these comfortable kicks. Smart enough for dressy occasions, their rubber sole can also stand up to the playground. Also available in camel.
To buy: $44, riverisland.com.
J. Crew Girls’ Tulle Backpack
Far too cute for school alone, she’ll want to tote this tulle-covered carryall everywhere. Also available in navy.
To buy: $60, jcrew.com.
Boys “Iron Knee” Lined Pull-On Beach Pants
Don’t let the name fool you: These durable chinos aren’t just for the beach. Lined with jersey, they’ll be cozy and warm, even as the mercury dips. Reinforced knees mean he can play as hard as he wants. Also available in grey.
To buy: $18, landsend.com.
Gap Instasia Graphic Crew Sweater
This knit update on camouflage gives it a slightly more refined look that both parent and child will love. Available in seven prints and colors.
To buy: $40, gap.com.