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Boys of all ages should get miles out of eye-catching sneakers that blend seamlessly with a wardrobe full of trusty basics. To find the hottest kicks and trendiest clothes, we scoured the racks at area stores to find back-to-school clothes that’ll impress on the first day and continue to work well into fall. Check below for age-appropriate outfit suggestions, shopping advice, and tips on how to wear new gear when the cold weather hits.

Elementary School

The shoe: Nike ‘Encore Jr.’ sneaker, $50, Nordstrom

The rest:
• Junk Food Transformer Graphic T-shirt, $22.50, Gap Kids
• Multitask Aztec Gold Backpack, $39.50, Lands End
• Rangeley Chinos, $24.50, L.L. Bean

This sneak’s gray base will keep recess kickball dirt from showing, and the multiple accent colors (blues! green! reds!) are guaranteed to go with the shirts and pants already in his closet. A Transformers-character T-shirt—dressed up with a vintage wash and controlled colored palette—will appease his action-figure appetite without looking cheap, and classic khakis can be worn to school and for more formal occasions. To top it all off, we picked a yellow padded backpack. The bright choice will make him easy to spot in kiss-and-drive line.

>> Next page: Middle school fashion

Middle School

The shoe: Lakai All-Weather Telford Skater Shoe, $72.95, Tactics.com

The rest:
• Hurley Blue Collar Brown Backpack, $32.50, PacSun
• Heather Carbon Merino Vest, $45, J.Crew
• Classic Navy Chino, $39.50, American Eagle
• Latham Pond White Button-down, $39.50, Abercrombie Kids

You can never go wrong with the sweater-vest/collared-shirt combo, but you can come off too stuffy. If he objects to dressing up for the first day, the unexpected color mash-up of these high-tops will give him a funky skater edge without ruining his good impression. Navy chinos are an equally versatile alternative to jeans, with the added bonus of meeting dress-code approval if denim doesn’t make the cut at his school. And we dare you to find a shirt that won’t work with this understated brown backpack. Its classic shape and boy-friendly neutral tone will take him well into high school.

>> Next page: High school fashion

High School

The shoe: Tretorn ‘Krona Mesh’ Sneaker, $69.95, Nordstrom

The rest:
• Eagle Marching Green Buffalo Check Shirt, $39.50, American Eagle
• Old Navy Regular Fit Jeans, $29.50, Old Navy
• AE Trek Backpack, $79.50, American Eagle

Teach him about understated design before he heads off to independent university life. Green buffalo plaid—a key trend for fall—will help him stand out while still looking smart, and the unexpected texture of this casual sneaker makes a goes-with-everything basic that’s worthy of a second look. In the halls, he’ll break from the Northface and Jansport standard with a leather-accented trekking bag, roomy enough for his lacrosse cleats and calculus books. When it comes to jeans, we recommend avoiding “loose fit” labels—the baggy shape will balloon from under the slim cut of the button-down, leading to an upside-down lightbulb silhouette. To maintain the natural line of the body, seek out tags with descriptions such as “classic fit,” “standard,” and “regular cut” instead.