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
All Boys

All Boys

(864 products)

Discover timeless elegance for your little gentleman! Our collection features adorable smocked bubbles, jon jons, and coordinating outfits perfect for every occasion. From heirloom-quality pieces to everyday essentials, find expertly crafted boys clothing with customizable monogram options that create cherished keepsakes for years to come.

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 (864)
Girls (146)
Women (3)

Clear

Features

Appliqué (80)
Embroidered (141)
Smocked (147)
Monogram (562)

Clear

Style

Bubbles (83)
Jon Jons (99)
Longalls (23)
Outerwear (17)
Pajamas (72)
Pant Sets (19)
Pants (27)
Rompers (44)
Shirts (234)
Shoes (5)
Short Sets (77)
Shorts (22)
Swimwear (19)
Backpacks (3)
Bags (21)
Baskets (2)
Belts (3)
Bibs (4)
Birthday (3)
Blankets (5)
Books (17)
Bracelets (2)
Hats (17)
Layette (8)
Lunch Boxes (4)
Seasonal (2)
Socks (8)
Sunglasses (2)
Towels (2)
Toys (20)

Clear

Size

Preemie (14)
Newborn (42)
3M (293)
6M (269)
9M (297)
12M (453)
18M (392)
24M (387)
2T (482)
3T (465)
4T (331)
5 (333)
6 (322)
7 (310)
8 (262)
10 (262)
12+ (42)
XS (27)
S (33)
M (33)
L (24)
XL (21)

Clear

Color

Blue (535)
Purple (31)
Pink (93)
Red (120)
Orange (29)
Yellow (24)
Green (155)
White (262)
Tan (25)
Brown (13)
Gray (7)
Black (12)
Metallic (5)
Multi (72)

Clear

Shoe Size

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

Clear

Brand

Angel Dear (1)
Apple Of My Isla (6)
Beyond Creations (1)
Bunnies by the Bay (1)
Classic Whimsy (654)
Floafers (1)
Jefferies Socks (8)
Magnolia Baby (6)
Mint (24)
Mud Pie (35)
Penguin Random House (10)
Petit Ami (2)
Southern Sunshine (107)
Sun-San (4)
Vive La Fete (1)
Wee Ones (1)
Zsa Zsa & Lolli (2)

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

Tan Stripe Short Sleeve Polo Romper

$42.85

Tan
New

Light Blue Stripe Long Sleeve Polo Romper

$42.85

Light Blue
New

Tan Stripe Long Sleeve Polo Romper

$42.85

Beige
New

Tan Stripe Long Sleeve Pocket Shirt

$35.70

Tan
New

French Blue Stripe Polo

$38.56

French Blue
New

Guitar Blue Stripe Long Sleeve Shirt

$31.42
New

Train Red Stripe Long Sleeve Shirt

$31.42
New

Train Smocked Blue Plaid Romper

$64.28
New

Train Smocked Blue Plaid Collared Bubble

$64.28
New

Train Smocked Blue Plaid Pant Set

$71.42
New

Sports Smocked Blue Stripe Short Set

$64.28
New

Sports Smocked Blue Stripe Jon Jon

$64.28
New

Sports Smocked Blue Stripe Pant Set

$71.42
New

Horse Smocked Light Blue Gingham Romper

$64.28
New

Construction Truck Smocked Blue Plaid Longall

$64.28
New

Construction Truck Smocked Blue Plaid Pant Set

$71.42
New

Mallard Smocked Tan Gingham Longall

$64.28
New

Mallard Smocked Tan Gingham Pant Set

$69.99
New

Mallard & Dog Smocked Brown Gingham Collared Bubble

$64.28
New

Mallard & Dog Smocked Brown Gingham Pant Set

$71.42
New

Mallard & Dog Smocked Brown Gingham Longall

$64.28
New

Brighton Plaid Collared Bubble

$57.13
New

Catch of the Day Embroidered Long Sleeve Pocket Shirt

$38.56
New

Catch of the Day Polo

$41.42
New

Catch of the Day Polo Romper

$42.85
New

Catch of the Day Pajamas

$47.13
New

Green & Navy Gingham Button Down Shirt

$39.99
New

Hampton Plaid Standard Pants

$31.42
New

Apple Trio Royal Blue Gingham Pajamas

$42.85

Royal Blue
New

School Adventure Blue Windowpane Polo Short Set

$49.99
New

School Adventure Pocket Shirt

$35.70

School Bus Blue
New

School Time Blue Stripe Short Sleeve Shirt

$35.70
New

Ready To Learn White Short Sleeve Shirt

$35.70
New

Bright Crayons Light Blue Stripe Polo

$38.56

Crayons Light Blue
Sharp Student Red Stripe Polo Short Set

$49.99
New

Apple Embroidered White Short Sleeve Henley Shirt

$35.70

Apple White
New

Apple Embroidered White Short Sleeve Pocket Shirt

$35.70

Apple White
New

Good Apple Blue Stripe Short Sleeve Henley Shirt

$35.70

Apple Royal Stripe
New

123 Blue Stripe Short Sleeve Pocket Shirt

$35.70

123 Royal Stripe
New

ABC Royal Blue Stripe Polo Romper

$42.85

ABC Royal Blue
New

ABC Royal Blue Stripe Polo

$38.56

ABC Royal Blue
New

Royal Blue Jogger

$31.42
New

Blue Stripe Sweatshirt

$35.70

Blue
New

Green Stripe Sweatshirt

$35.70

Green
New

Easy as 123 White Polo

$41.42

Easy as 123
New

Easy as 123 White Short Pajamas

$38.56

Easy as 123
New

Easy as 123 White Polo Romper

$42.85

Easy as 123
New

White Long Sleeve Bodysuit

$35.70

Previous
Page 2 / 18
1
2
3
4
…
18
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