I love little man in plaid shorts. My mom got these Gymboree Shark Alert ones super-cheap last winter. I paired it with a Carter's Rocket tee and Circo seersucker shoes.
Tillie's wearing a Matilda Jane Bobbi Jo dress and Polkie Flare leggings. She's worn this before, but I think it might have been layered every time it's been on the blog.