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Save up to 60% OFF our entire range of carter's and OshKosh styles. Prices as marked

Selected discounts applied at checkout on full price items only, no voucher code necessary. Online only offer, all stores are currently closed. Excludes Accessories, Skip Hop, sale items, and other promotions.

Toddler Boy Dress Up

Dress Up

Shop a great range of toddler boy dress up collection including cute clothing sets, jackets, button shirts, chinos, dress shoes and accessories to make your little man party ready.

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(59 Products)
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Button-Front Shark L/S Shirt
New Arrival
| Todder Boy
Button-Front Shark L/S Shirt
$36.00
$25.19*
Save 30% OFF
Plaid Button-Front L/S Shirt
New Arrival
| Todder Boy
Plaid Button-Front L/S Shirt
$34.00
$23.79*
Save 30% OFF
Uniform Twill Pants
New Arrival
| Todder Boy
Uniform Twill Pants
$40.00
$27.99*
Save 30% OFF
Uniform Twill Pants
New Arrival
| Todder Boy
Uniform Twill Pants
$40.00
$27.99*
Save 30% OFF
Shawl Collar Cardigan
Best Seller
| Toddler Boy
Shawl Collar Cardigan
$50.00
$30.00*
Save 40% OFF
Velcro Oxford Dress Shoes
Online ExclusiveOnline Only
| Toddler Boy
Velcro Oxford Dress Shoes
$50.00 $30.00
High-Top Double Strap Sneakers
Online ExclusiveOnline Only
| Toddler Boy
High-Top Double Strap Sneakers
$45.00 $30.00
High-Top Double Strap Sneakers
Online ExclusiveOnline Only
| Toddler Boy
High-Top Double Strap Sneakers
$45.00 $30.00
High-Top Triple Strap Sneakers
Online ExclusiveOnline Only
| Toddler Boy
High-Top Triple Strap Sneakers
$45.00 $30.00
Sailboat Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Sailboat Button-Front Shirt
$40.00
$27.99*
Save 30% OFF
Skating Bananas Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Skating Bananas Button-Front Shirt
$40.00
$27.99*
Save 30% OFF
Plaid Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Button-Front Shirt
$40.00
$27.99*
Save 30% OFF
Plaid Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Button-Front Shirt
$40.00
$27.99*
Save 30% OFF
Denim Jacket
Online ExclusiveOnline Only
| Toddler Boy
Denim Jacket
$80.00 $52.00
Plaid Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Button-Front Shirt
$40.00
$27.99*
Save 30% OFF
Twill Flannel Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Twill Flannel Button-Front Shirt
$34.00
$20.40*
Save 40% OFF
Plaid Twill Flannel Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Twill Flannel Button-Front Shirt
$34.00
$20.40*
Save 40% OFF
Plaid Twill Flannel Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Twill Flannel Button-Front Shirt
$34.00
$20.40*
Save 40% OFF
Plaid Poplin Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Poplin Button-Front Shirt
$30.00
$18.00*
Save 40% OFF
Suspenders
| Toddler Boy / Boy
Suspenders
$18.00
$10.80*
Save 40% OFF
3-Piece Plaid Dress Me Up Set
| Toddler Boy
3-Piece Plaid Dress Me Up Set
$60.00
$36.00*
Save 40% OFF
3-Piece Gingham Dress Me Up Set
| Toddler Boy
3-Piece Gingham Dress Me Up Set
$60.00
$36.00*
Save 40% OFF
3-Piece Schiffli Dress Me Up Set
Best Seller
| Toddler Boy
3-Piece Schiffli Dress Me Up Set
$60.00
$36.00*
Save 40% OFF
3-Piece Dinosaur Dress Me Up Set
| Toddler Boy
3-Piece Dinosaur Dress Me Up Set
$60.00
$36.00*
Save 40% OFF
Twill Pants
Online ExclusiveOnline Only
| Toddler Boy
Twill Pants
$38.00
$22.80*
Save 40% OFF
Checkered Twill Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Checkered Twill Button-Front Shirt
$32.00 $16.00
Plaid Twill Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Twill Button-Front Shirt
$32.00 $16.00
Button-Front Flannel Shirt
Online ExclusiveOnline Only
| Toddler Boy
Button-Front Flannel Shirt
$40.00 $20.00
Button-Front Plaid Shirt
Online ExclusiveOnline Only
| Toddler Boy
Button-Front Plaid Shirt
$36.00 $18.00
Plaid Button-Front Shirt
Online ExclusiveOnline Only
| Toddler Boy
Plaid Button-Front Shirt
$36.00 $18.00
Long Sleeve Button-Front Shirt
| Toddler Boy
Long Sleeve Button-Front Shirt
$36.00
$25.19*
Save 30% OFF
Long Sleeve Striped Uniform Shirt
| Toddler Boy
Long Sleeve Striped Uniform Shirt
$36.00
$25.19*
Save 30% OFF
Long Sleeve Button-Front Shirt
| Toddler Boy
Long Sleeve Button-Front Shirt
$36.00
$25.19*
Save 30% OFF
Logo Polo
| Toddler Boy
Logo Polo
$26.00
$18.19*
Save 30% OFF
Button-Front Surf Shirt
| Toddler Boy
Button-Front Surf Shirt
$36.00
$25.19*
Save 30% OFF
Button-Front Shark Shirt
| Toddler Boy
Button-Front Shark Shirt
$36.00
$25.19*
Save 30% OFF
Suspender Pants
| Toddler Boy
Suspender Pants
$48.00
$33.59*
Save 30% OFF
Checkered Poplin Button-Front Shirt
Clearance
| Toddler Boy
Checkered Poplin Button-Front Shirt
$34.00 $16.85
Plaid Poplin Button-Front Shirt
Clearance
| Toddler Boy
Plaid Poplin Button-Front Shirt
$34.00 $16.85
Striped Poplin Button-Front Shirt
Clearance
| Toddler Boy
Striped Poplin Button-Front Shirt
$30.00 $12.85
Plaid Poplin Button-Front Shirt
Clearance
| Toddler Boy
Plaid Poplin Button-Front Shirt
$30.00 $12.85
Velcro Uniform Sneaker
Clearance
| Toddler Boy
Velcro Uniform Sneaker
$40.00 $19.85
Camo Pull-On French Terry Shorts
| Toddler Boy
Camo Pull-On French Terry Shorts
$24.00 $20.00
Plaid Poplin Button-Front Shirt
Online ExclusiveOnline Only
Clearance
| Toddler Boy
Plaid Poplin Button-Front Shirt
$28.00 $9.85
Button-Front Striped Shirt
Online ExclusiveOnline Only
Clearance
| Toddler Boy
Button-Front Striped Shirt
$40.00 $19.85
Button-Front Plaid Shirt
Online ExclusiveOnline Only
Clearance
| Toddler Boy
Button-Front Plaid Shirt
$40.00 $19.85
Button-Front Plaid Shirt
Online ExclusiveOnline Only
| Toddler Boy
Button-Front Plaid Shirt
$40.00 $20.00
Button-Front Plaid Shirt
Online ExclusiveOnline Only
Clearance
| Toddler Boy
Button-Front Plaid Shirt
$38.00 $17.85

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