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