Your debonair tot can still be smooth as silk in raingear. Or not! But you can still have your fantasy. If you promise you’ll let him splash in puddles, you’re sure to get your way when you want to dress him up like Fred Astaire. Good thing he has no clue who Fred Astaire is! : ) This rainy-day outfit is an instant classic: crisp, casual, with a splash of prep and just dapper enough.

J.Crew’s unfussy button-down ($49.50) (nothing too formal) looks all grown up, especially with a pair of Ralph Lauren’s well-fitting cotton chinos ($39.50), and it sets an un-sloppy mood for a quintessential piece of raingear, the bright-yellow slicker ($64.95), like Hatley’s outdoorsy number. Add a striped silk tie for some polish – and a hint of irony snobs old and young will appreciate – and a quirky umbrella for his sake (playful umbrellas make wet days so much more fun), like Western Chief’s Monster umbrella ($15.95), and he might even just burst into song.