Rugged enough for the playground and cool enough for the classroom, these washed Levi's jeans are as comfortable as they are laid-back.
Levi's Boys Husky 505 Straight Fit Jean
Price: $22.99
Classic sports style in this polo shirt from Guess will pull his outfit together and keep him comfortable all day.
Guess Kids Shirt, Boys Crown Jersey Polo Shirt
Price: $32.50
Time to salute! He'll be proud to show off his patriotic side in these stars-and-stripes swim trunks from Tommy Hilfiger.
Tommy Hilfiger Boys Swimwear, Stars and Stripes Swim Trunks
Price: $35.60
Bundle him up with this classic preppy peacoat from Weatherproof.
Weatherproof Kids Jacket, Little Boys Double Breasted Peacoat
Price: $25.99
The jeans make the look.   Sandblasting adds a cool vintage look to these jeans from Tommy Hilfiger.
Tommy Hilfiger Kids Jeans, Boys Revolution Jean
Price: $34.50
Playful in plaid. Get him ready for the day in these stylish and comfortable flat-front shorts from Nautica.
Nautica Kids Short, Boys Flat Front Plaid Shorts
Price: $25.50
This jacket from DKNY has plenty of pop for his layered look.
DKNY Kids Jacket, Boys Hudson Jacket
Price: $44.62
Worn off the shoulders or cowl neck-style, this slouchy HELMUT shirt is a no-fail choice to pair with moleskin leggings or love-worn denim come fall weekends.
HELMUT Shirt - Slouchy
Price: $125.00
Sharpen up his summer style with a pair of plaid cargo shorts from Tommy Hilfiger.
Tommy Hilfiger Kids Shorts, Boys Darren Cargo Short
Price: $33.37
Give your wrist a shot of golden glamour with Michele's luxe new season straps.
Michele Golden Leather Strap
Price: $120.00
The ever-classic yet always stylish sailor pant channels breezy, summery appeal with a flowy, wide-leg silhouette of lightweight cotton twill.
Lauren Ralph Lauren Nicklaus Cotton Twill Sailor Pants
Price: $69.65
Pop some preppy plaid into his warm-weather wardrobe with this short-sleeved woven shirt from Nike.
Nike 6.0 Kids Shirt, Boys Plaid Shirt
Price: $22.80
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