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
Size 'em up! Elastic at the sides of the waist will make these Epic Threads cargo shorts fit perfectly and keep him looking good all day long.
Epic Threads Kids Shorts, Boys Plaid Cargo Shorts
Price: $14.99
These platform pumps are double the fun, with a layered sole that elevates them to new heights. Plaid uppers are perfect for Anglophiles; from Cole Haan.
Cole Haan Platform Pumps - Chelsea High Heel
Price: $428.00
Way to be flexible! This long-sleeved shirt from Tommy Hilfiger can be dressed up or down for effortless style and comfort on any occasion.
Tommy Hilfiger Boys Shirt, Wahler End On End Shirt
Price: $31.60
Those three stripes mean quality. Get him a a pair of comfy adidas pants and know you're getting the best.
adidas Boys Tricot Pants
Price: $24.00
He won't be singing the blues with these jeans from Akademiks.  A matching belt completes his cool denim look.
Akademiks Kids Jeans, Boys Relaxed Fit Jeans
Price: $31.20
Walk the line. He'll have no problem feeling confident and stepping up in one of these take-notice striped shirts from Tommy Hilfiger.
Tommy Hilfiger Boys Shirt, Short Sleeve Wayne Stripe Tee
Price: $19.60
Pop some plaid in to his daily rotation with this roll-tab sleeve woven shirt from DKNY
DKNY Kids Shirt, Boys Sheridan Roll-Up
Price: $28.12
Freshen up his warm-weather wardrobe with a pair of these airy-feeling plaid shorts and matching belt from Guess.
Guess Kids Shorts, Boys Tariff Belted Plaid Shorts
Price: $46.50
Plaid shows just how rad his style is with this tee shirt from Hurley.
Hurley Kids Shirt, Boys Plaid Tee Shirt
Price: $14.00
These Puma tricot track pants are ideal for warm-ups, cool downs and everything in-between.
Puma Kids Pants, Boys Tricot Pants
Price: $27.00
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