Skip to content

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

Search

Account Log in Cart

Menu

New
Christmas

Black Friday

Pumpkin Patch
Girls
Black Friday

Christmas
Boys
Black Friday

Christmas
Baby
Classic Knits

Monogram Bloomers
Black Friday
Collections
Black Friday

Christmas
Sale

Christmas Shipping Deadline:

11/20 Monogram Orders; 12/11 Non-Monogram Orders

Home
All Boys

All Boys

(847 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
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 (24)
Girls (10)

Clear

Features

Embroidered (3)
Monogram (14)

Clear

Style

Jon Jons (1)
Pajamas (2)
Pant Sets (2)
Pants (2)
Shirts (6)
Shoes (3)
Shorts (3)
Belts (2)
Hats (2)
Socks (1)

Clear

Size

Preemie (1)
Newborn (1)
3M (4)
6M (4)
9M (4)
12M (5)
18M (4)
24M (4)
2T (13)
3T (11)
4T (13)
5 (13)
6 (13)
7 (14)
8 (12)
10 (14)
12+ (7)
XS (2)
S (2)
M (4)
L (3)
XL (3)

Clear

Color

Blue (10)
Purple (4)
Pink (3)
Red (5)
Orange (7)
Green (1)
White (11)
Tan (3)
Brown (4)
Gray (1)
Black (1)

Clear

Shoe Size

Baby 3 (1)
Baby 4 (2)
Child 5 (1)
Child 6 (2)
Child 7 (2)
Child 8 (2)
Child 9 (2)
Child 10 (2)
Child 11 (2)
Child 12 (2)
Child 13 (2)

Clear

Brand

Chus (1)
Classic Whimsy (18)
Floafers (1)
Jefferies Socks (1)
Southern Sunshine (2)
Sun-San (1)

Clear

Sort by

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

Sale

Stone Standard Shorts

$21.27 ~~$28.37~~

Stone
Sale

French Blue Standard Shorts

$21.27 ~~$28.37~~

French Blue
Sale

Stone Standard Pants

$21.27 ~~$31.21~~

Stone
Sale

Game Day Football Jogger Set

$28.37 ~~$49.66~~
Sale

Game Day Football Short Pajamas

$14.18 ~~$38.30~~

Orange Purple Light Blue Red Pink Maroon
New

White Jogger Set

$42.56

White
Sale

Navy Standard Pants

$21.27 ~~$31.21~~

Navy
New

Solid Long Sleeve Polo Shirt White

$35.47

White
Sale

Kids Leather Belt

$21.27 ~~$35.47~~
Sale

Kids Woven Belts

$21.27 ~~$35.47~~

Light Blue/Orange Red/Blue Navy Navy/Light Blue Blue Brown
Sale

Solid Kids Hat

$8.50 ~~$14.18~~

White Light Blue Navy Pink
Sale

Navy Standard Shorts

$21.27 ~~$28.37~~

Navy
Sale

Solid Pique Polo Shirt White

$11.34 ~~$35.47~~

White
Sale

Clemson Embroidered Orange Performance Polo

$35.47 ~~$63.85~~
Sale

Clemson Embroidered Orange Jon Jon

$35.47 ~~$69.53~~
Sale

Orange Stripe Polo

$14.18 ~~$35.47~~
Sale

Purple Stripe Polo

$14.18 ~~$35.47~~
Sale

Collegiate Logo Kids Hat

$14.18 ~~$31.22~~

Alabama Arkansas Auburn Baylor Clemson White/Orange Clemson FSU +13
Sale

Game Day Football Pajamas

$21.27 ~~$46.82~~

Purple Pink Orange Maroon Light Blue Red
Sale

Prodigy Driver Loafers

From $42.58 ~~$63.86~~

Driftwood/Coconut Navy/White Bone/White Sky Blue/White
Sale

White Knit Polo Shirt

$14.18 ~~$35.47~~
Unisex White Knee High Socks (2 Pack)

$12.77
White Surfer Sandals

$65.21
Sale

Chris Canvas Shoe

$28.37 ~~$45.41~~

Red Navy White

Shop Collection Favorites!

Christmas

Shop
Valentine's Day

Shop
Black Friday

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

© 2025 Classic Whimsy.

About Us
Blog
Safety & Recall