A look that's skilled at the art of cool: the 511 skinny jean from Levi's.
Levi's Kids Pant, Boys Regular Student 511 Skinny Jean
Price: $26.99
Narrow down the choices with these slim fit, straight leg jeans from Levi's that always wear well.
Levi's Boys Slim 514 Slim Straight Jean
Price: $26.99
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Levi's Kids 511 Jeans, Boy Skinny Fit Husky Jeans
Price: $28.99
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
Cool weather calls for cooler layers and these pieced tees from Industry 9 are just what fits.
Industry 9 Kids Shirt, Boys Long Sleeve Layered Thermal
Price: $14.99
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
Catch the wave! He'll be ready to run full-force into the water with these comfy, drawstring swim trunks from Nike.
Nike Boys Shorts, Tidal Wave Splice Swim Trunks
Price: $21.99
Surf style for you beach boy. This casual tee from O'Neill is sand-tastic.
O'Neill Kids Shirt, Boys Graphic Tee Shirt
Price: $13.50
Combining the preppy look of of a plaid woven with the skater style of a hoodie makes this a combination from Timberland you'll both love.
Timberland Kids Shirt, Boys Hooded Woven Shirt
Price: $33.00
When he wants casual style that pops, turn to this preppy polo from Guess.
Guess Kids Shirt, Boys Short Sleeved Polo
Price: $32.50
A husky take on the easy-wearing, stylishly slim 514 jeans from Levi's.
Levi's Kids Jeans, Boys Vintage Husky 514 Slim Straight Jeans
Price: $27.99
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