Show:
Sort By:

The Bailey Boys J. Bailey Button Down December Plaid

We love this December plaid button-down for everything from holiday portraits to parties. It’s semi-fitted with a classic button-down collar and buttoned sleeves, finished with the embroidered Bailey Boys logo.

$44.00

The Bailey Boys J. Bailey Button Down Holly Plaid

Holiday party on the agenda? We've got just the thing. The fun Holly Plaid and button cuffs make this classic button-down shirt super smart, and the cozy cotton material means there's absolutely nothing getting in the way of a good time.

$44.00

The Bailey Boys J. Bailey Button Down Kaleidoscope Plaid

Bold and bright, this Oxford is ready to steal the spotlight. Perfect for any smart occasion, it has a classic button-down front with buttoned sleeves, and features a kaleidoscope of fun colors, finished with the Bailey Boys logo.

$44.00

The Bailey Boys J. Bailey Button Down Pumpkin Windowpane

Made in ‘Pumpkin Windowpane,' this Oxford style shirt is just the thing for autumn. This semi-relaxed shirt has a classic button-down collar and is made from soft cotton for a comfy fit. Perfect for the pumpkin patch, apple picking or other family outings

$44.00

The Bailey Boys J Bailey Champ Cinnamon Twill

Whenever a smart occasion calls, these Cinnamon Twill trousers are up to the task. The relaxed fit means all-day comfort, while the loops make adding an adjustable (and stylish) belt easy as 1-2-3.

$48.00

The Bailey Boys Ribbon Belt Chocolate Dog

Buddy Belt Sizing:
Small 20" - 2T & 3T
Medium 22" - 4T/4R & 5
Large 24" - 6 & 7
Extra Large 26" - 8, 10 & 12

$36.00

The Bailey Boys J Bailey Button Down Shirt Easter Basket

Made in 'Easter Basket Plaid,' this Oxford style shirt is just the thing for the holidays. This semi-relaxed shirt has a classic button-down collar and is made from soft cotton for a comfy fit. Perfect for meeting the Easter bunny or other family outings—

$45.00
$27.00

The Bailey Boys J Bailey Button Down Shirt Montauk

The recipe for the perfect shirt? Take one Oxford-style fit, craft it in soft cotton, mix fun colors together and add a dash of cuteness (that's the Bailey Boy's logo, of course). The result: one super-smart yet comfortable button-down shirt, perfect for

$45.00
$27.00

The Bailey Boys J Bailey Button Down Shirt Bubblegum

Smart occasion? No problem. This semi-fitted shirt is just the ticket for looking sharp in no time. This cotton Oxford style has a classic button-down collar and comes in bubblegum plaid, finished with the Bailey Boys logo.

$45.00
$27.00

The Bailey Boys J Bailey Pete Short Sky Linen

Crafted from lightweight linen, these sky blue shorts just feel like summer days. The perfect combination of comfy and smart, these shorts are great for everything from a birthday party with friends or a smart occasion with the grownups. Just pop in a sty

$60.00
$36.00

The Bailey Boys J Bailey Pete Mint Stripe Seersucker Pete Short

Stay smart while keeping cool this summer, thanks to these crisp shorts. Made from lightweight fabric, these striped shorts are easy to pull on for mornings on the go, and can be dressed up with a belt and polo or paired with a tee for laidback weekends.

$44.00
$26.40

The Bailey Boys J Bailey Pant Sky Linen

Crafted from lightweight linen, these sky blue pants just feel like summer. These trousers are the perfect combination of comfy and smart.

$48.00
$28.80

The Bailey Boys J Bailey Champ Pants White

The durable Champ pant is a must-have in any young man’s wardrobe. Their classic fit is designed to move and flatter, with thoughtful details like elastic at the waist and buttoned back pockets.

$48.00
$28.80

The Bailey Boys J Bailey Hunter Plaid Pant

Whether your little man is heading to the park or joining a playdate, these hunter plaid trousers are the perfect combination of smart and comfortable.

$50.00

The Bailey Boys J. Bailey Button Down Shirt Wales Plaid

Classic, casual, colorful—the perfect all-rounder. Featuring a classic button-down collar, this red and green plaid shirt looks great paired with trousers. Button it up for special occasions, or wear it loose when playtime comes around.

$44.00

The Bailey Boys J Bailey Short Sleeve Polo Light Blue

Nothing says prep school charm like a well-made polo. Sporty yet polished, it's the kind of shirt a young man can wear anywhere. These polos have a tailored fit, wonderfully soft knit, and the distinct J. Bailey logo.

$36.00

The Bailey Boys J Bailey Cord Pant Chocolate

Champ Pant Design:
Adjustable elastic waistband for custom fit.
Five belt loops
Two back pockets with button closure
Two front pockets
Sizes 2T through 4T/4R are full elastic waist band (no zipper)
Sizes 5-12 design include c

$48.00

The Bailey Boys J Bailey Champ Pant Navy Cord

Champ Pant Design:
Adjustable elastic waistband for custom fit.
Five belt loops
Two back pockets with button closure
Two front pockets
Sizes 2T through 4T/4R are full elastic waist band (no zipper)
Sizes 5-12 design include c

$48.00

The Bailey Boys J Bailey Champ Pant Forest Cord

Champ Pant Design:
Adjustable elastic waistband for custom fit.
Five belt loops
Two back pockets with button closure
Two front pockets
Sizes 2T through 4T/4R are full elastic waist band (no zipper)
Sizes 5-12 design include c

$48.00

The Bailey Boys J Bailey Pete Short

Get the island prep look with this enduring summer staple. The Pete shorts have a classic fit and come in at just the right length for style and comfort.

$42.00