Skip to content

MAKE EVERY MOMENT A MILESTONE! Enjoy free US shipping on orders over $150

Search

Account Log in Cart

Menu

New
Back to School

Collegiate

Swimwear
Girls
Back to School

Collegiate
Boys
Back to School

Collegiate
Baby
Classic Knits

Monogram Bloomers
Back to School
Collections
Back to School

Collegiate
Sale

Home
Back to School Playwear

Back to School Playwear

(250 products)

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

FiltersFilter & Sort

Applied Filters

Clear all

Gender

Boys (135)
Girls (120)

Clear

Features

Appliqué (20)
Embroidered (26)
Smocked (8)
Monogram (175)

Clear

Style

Bloomer Sets (7)
Bubbles (4)
Dresses (48)
Jon Jons (3)
Outerwear (15)
Pajamas (1)
Pant Sets (5)
Pants (24)
Rompers (12)
Shirts (81)
Shoes (5)
Short Sets (30)
Shorts (9)
Belts (2)
Bows (1)
Hats (3)

Clear

Size

Newborn (4)
3M (35)
6M (34)
9M (36)
12M (132)
18M (122)
24M (125)
2T (212)
3T (209)
4T (189)
5 (187)
6 (189)
7 (188)
8 (177)
10 (185)
12+ (30)
XS (2)
S (2)
M (3)
L (2)
XL (2)

Clear

Color

Blue (129)
Purple (10)
Pink (44)
Red (45)
Orange (3)
Yellow (3)
Green (26)
White (45)
Tan (12)
Brown (3)
Gray (3)
Black (4)
Metallic (2)
Multi (10)

Clear

Bow Size

Baby (1)
Tiny (1)
Mini (1)
Medium (1)
King (1)
Huge (1)

Clear

Shoe Size

Baby 3 (3)
Baby 4 (3)
Child 5 (4)
Child 6 (4)
Child 7 (5)
Child 8 (5)
Child 9 (5)
Child 10 (5)
Child 11 (5)
Child 12 (5)
Child 13 (5)
Youth 1 (1)

Clear

Brand

Cienta (1)
Classic Whimsy (238)
Southern Sunshine (6)
Sun-San (4)
Wee Ones (1)

Clear

Sort by

Featured
Most relevant
Best selling
Alphabetically, A-Z
Alphabetically, Z-A
Price, low to high
Price, high to low
Date, old to new
Date, new to old

New

Sharp Student Red Stripe Polo Short Set

$50.43
New

Sweet Apple Trio Pink Stripe Avery Dress

$53.32 ~~$0.00~~
New

School Days Smocked Navy Plaid Jon Jon

$64.85
New

School Ready Smocked Blue Plaid Jon Jon

$64.85
New

School Ready Smocked Blue Plaid Short Set

$64.85
New

Colorful Crayon Smocked Blue Gingham Short Set

$64.85
New

Red Apple Smocked Blue Gingham Short Set

$57.64
New

Red Plaid Short

$28.81
New

School Time Blue Stripe Short Sleeve Shirt

$36.02
New

School Adventure Pocket Shirt

$36.02

School Bus Blue
New

School Adventure Blue Windowpane Polo Short Set

$50.43
New

Navy Blue Standard Pants

$31.70

Navy
Construction Truck Applique Blue Jogger Set

$50.43
New

Gray Jogger

$31.70

Gray
New

Pink Gingham Abby Dress

$53.32
New

Bow Applique Abby Dress

$53.32
New

Tan Gingham Standard Pants

$31.70

Tan
New

Green Gingham Standard Pants

$31.70

Green
New

Royal Blue Gingham Standard Pants

$31.70

Royal Blue
New

Royal Blue Gingham Pants

$31.70

Royal Blue
Bow Applique Pink Gingham Jogger Set

$50.43
Mallard Applique Blue Jogger Set

$50.43
New

Light Blue Gingham Standard Pants

$31.70

Light Blue
New

White Long Sleeve Polo Shirt

$36.02

White
Sale

Light Blue Solid Long Sleeve Pique Polo Shirt

$8.63 ~~$36.02~~

Light Blue
Sale

Light Blue Stripe Short Sleeve Pocket Shirt

$24.49 ~~$33.14~~

Light Blue
New

Red Solid Short Sleeve Pocket Shirt

$33.14

Red
New

Milly Stripe Ruffle Dress Royal

$38.90

Royal Blue
New

Milly Stripe Ruffle Dress Red

$38.90

Red
New

School Bus Smocked Royal Gingham Short Set

$57.64
New

Riley Stripe Knit Long Sleeve Dress Purple

$43.23

Purple
New

Riley Stripe Knit Long Sleeve Dress Pink

$43.23

Pink
New

French Blue Riley Stripe Knit Long Sleeve Dress

$43.23

French Blue
Pink Stripe Long Sleeve Polo

$36.02
Kids Leather Belt

$36.02
New

Kids Woven Belts

$36.02

Brown Navy/Light Blue Navy Blue Light Blue/Orange Red/Blue
New

Light Blue Gingham Pants

$31.70

Light Blue
New

Solid Kids Hat

$14.40

White Light Blue Navy Pink
Sale

Stripe Kids Hat

$12.96 ~~$18.72~~

Pink Light Blue
New

Navy Standard Shorts

$28.81

Navy
New

Lavender Stripe Knit Short Sleeve Polo

$36.02

Lavender
Sale

Solid Pique Polo Shirt White

$21.61 ~~$36.02~~

White
New

Turquoise Stripe Knit Short Sleeve Polo

$36.02

Turquoise
New

Emerald Green Stripe Knit Short Sleeve Polo

$36.02

Green
Sale

Navy Stripe Knit Short Sleeve Polo

$28.81 ~~$36.02~~

Navy
New

Crimson Red Stripe Knit Short Sleeve Polo

$36.02

Red
New

Cartwheel Shorts (3-Pack)

$36.02

Essential Pastel Pink Party Uniform Black Out White Out
Cartwheel Shorts

$14.40

Light Pink Navy White Light Blue Hot Pink Black

Previous
Page 2 / 6
1
2
3
4
…
6
Next

Shop Collection Favorites!

Beach

Shop
Collegiate

Shop
Back to School

Shop

Your cart

Your cart is empty

Subtotal:$0.00 CAD

Loading...

Facebook
Instagram
TikTok
Pinterest

Customer Care

Contact Us
FAQ
Rewards
Shipping
Size Guide
Returns

Shop

New
Girls
Boys
Baby
Collections
Sale

Newsletter

Sign up for exclusive offers, original stories, events and more.

Email

© 2026 Classic Whimsy.

About Us
Blog
Safety & Recall