A gingham pattern delivers stellar style and maximum comfort in this button-front shirt from Sean John.
Sean John Kids Shirt, Boys Gingham Shirt
Price: $39.50
A classy combination of preppy and casual, this polo-style shirt from Quiksilver goes with just about anything.
Quiksilver Kids Shirt, Big Boys Polo Shirt
Price: $19.20
Build up the basics. A collared, button down shirt from Calvin Klein gets stylish with stripes and can dress up any pair of jeans or pants.
Calvin Klein Kids Shirt, Boys Button Down Stripe Shirt
Price: $29.62
Stuart Weitzman proves that ballet flats can be bold and fashion forward-anything but dainty in bright, snake print leather. Plush suede linings will make these a go-to.
Stuart Weitzman Flats - Giveable Ballet
Price: $298.00
Santa reviews his nice list surrounded by toys, all atop the iconic little brown bag decked in glittering snow.
Bloomingdale's Santa's Little Brown Bag Toy Ornament
Price: $16.00
Casual or dressy, he'll clean up well in this long-sleeved plaid shirt from Nautica.
Nautica Kids Shirt, Boys Plaid Long Sleeve Shirt
Price: $29.62
Tie it all together. He'll have the complete dapper look with this long-sleeved woven and tie combination from Izod.
Izod Kids Set, Boys Shirt and Tie Set
Price: $19.50
From school to the game and everywhere else, this plaid shirt from Nautica will keep him comfortable and looking good.
Nautica Kids Shirt, Boys Long Sleeve Plaid Shirt
Price: $23.69
Game, set, match. Whether he's cheering or playing, he'll be comfortable in this Tommy Hilfiger polo.
Tommy Hilfiger Kids Shirt, Boys Blade Applique Polo
Price: $21.09
He'll be cool under pressure in this color-blocked, dry fit shirt from Champion.
Champion Boys Shirt, Color Blocked Dry Fit Tee
Price: $17.00
There's no questioning a classic: these Tommy Hilfiger khakis are a forever favorite.
Tommy Hilfiger Boys Khaki Pants
Price: $29.50
This comfy tee shirt from Quiksilver will easily stack up against the rest of his favorites in the closet.
Quiksilver Kids Shirt, Boys Graphic Tee Shirt
Price: $14.40
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