A whimsical illustration depicts a red-haired girl with fair skin, wearing a black and white striped coat dress, black tights, and black shoes, walking a polka-dotted dog on a leash in a strong autumn breeze. Her long, fiery red hair blows to the left, as does her striped scarf and the dog. She struggles to hold onto a red polka-dotted umbrella, which is inverted by the wind. Her eyes are wide and focused to the upper left. The dog, a white creature with black spots and a red collar, is mid-air, its black ears flapping. Autumnal red and orange leaves are being swept by the wind from a tall, thin tree with a white trunk and delicate branches on the left side of the frame. In the background, a town with colorful houses, some with illuminated windows, lines the horizon next to a body of water with a ship. The sky is streaked with light blue and peach hues, suggesting either dawn or dusk. A street lamp on the right is also lit. The ground is dry and textured, with a few scattered leaves. The overall style is illustrative with a hand-drawn quality, featuring fine lines and textured shading.