Plaid for the win! He'll look relaxed yet stylish in this button-down Tommy Hilfiger plaid shirt.
Tommy Hilfiger Boys Shirt, Boys Long-Sleeved Plaid Shirt
Price: $23.70
A little rough-and-tumble, a little preppy. A plaid shirt from Epic Threads shows he has more than one side to his personality.
Epic Threads Kids Shirt, Boys Plaid Long Sleeved Shirt
Price: $22.49
Whether it's school or just out-and-about, this plaid shirt from Tommy Hilfiger will keep him comfortable and looking great.
Tommy Hilfiger Kids Shirt, Boys Long Sleeve Plaid Shirt
Price: $31.60
Give him structure. Add some artistic appeal to his closet with this modern graphic tee shirt from O'Neill.
O'Neill Kids Shirt, Boys Chaos Graphic Tee
Price: $14.40
Put some prep in his step with one of these Sean John short-sleeved polos.
Sean John Kids Shirt, Boys Garrison Polo
Price: $22.50
As bold as your boy. This solid, vibrant pique polo from Nautica adds plenty of comfort and versatility to his everyday lineup. It's also a great staple for uniforms.
Nautica Kids Shirt, Boys Solid Pique Polo
Price: $19.99
Fashion victim? Hardly; more like fashion victor; these boldly stylish Ash sneakers feature over-the-top studs and styling that will take basic looks above and beyond.
Ash High Top Sneakers - Victim
Price: $225.00
A squared logo plate lends a 60s feel to Tory Burch's retro-inspired Julian pumps, dressed up with patent piping.
Tory Burch Pumps - Julian High Heel
Price: $325.00
Style stays simple with these Quiksilver board shorts so the only things that stand out are his swimming skills.
Quiksilver Kids Swimwear, Boys Board Short
Price: $11.24
Surfs up! He'll have no worries, and you won't either, as he rushes the water in this rash guard from iXtreme.
iXtreme Kids Swimwear, Little Boys Surfer Rashguard
Price: $10.99
He'll never have to try too hard in one of these long-sleeved polo shirts Tommy Hilfiger that will make him a natural at style.
Tommy Hilfiger Kids Shirt, Boys Long-Sleeved Polo Shirt
Price: $21.25
In the paint. He'll score casual style points with this colorful tee shirt from Hurley.
Hurley Kids Shirt, Boys Drip Logo Tee
Price: $13.50
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