There’s something about late August and early September that makes you want to get your act together. Maybe it’s years of conditioning from freshly sharpened pencils and brand-new notebooks, but even when you haven’t seen the inside of a classroom in decades, back-to-school season still feels like a chance to reset. And that applies to your wardrobe, too. Fall is coming, layers will soon be possible again and suddenly getting dressed feels interesting after months of shorts and T-shirts.

So we’re borrowing a few things from the old school uniform and giving them a decidedly grown-up upgrade. Think a slightly boxy oxford under a collegiate cotton crewneck, relaxed chinos or cords and substantial loafers instead of beat-up sneakers. Add a handsome watch and a slouchy leather tote for a look that’s nostalgic without feeling like you’re headed to homeroom. It’s a little Ivy, a little prep and a lot more sophisticated than what you wore the first time around.