Gustave Caillebotte’s Paris “Street: A Rainy Day” portrays the urban and historical intersection between high fashion and the brutal urban regeneration of late-nineteenth century capitalism. As the artist lived and matured in his work all around him were felt the upheavals of Baron von Haussmann’s urban regeneration of Paris. Indeed, it was the destruction of the medieval alleyways and ancient settlements that drove the Impressionist cohort to create their rural idyll. The result of the unprecedented urban renewal was the boulevards that characterize contemporary Paris. Paris “Street: A Rainy Day”, painted in 1877 captures the precise moment when the urban world changed, incorporating convenient train travel, city-fashion, street photography, and urban modernity. Although unrecognizable today from Caillebotte’s canvas, the Place de Dublin was once a hub of couples walking down the newly carved streets. To late-nineteenth century eyes the painting would have been a stunning vision of an almost-futuristic environment. The stark, geometric lines, the fashionable threads and English-style umbrellas that the strollers hold with pride, and the photo-realistic framing of the painting, all stand as a testament to the changing tastes of a culture propelling itself towards mass-production and modernity. Lingering in the edges of the frame are hints of scaffolding and with it the potential of further regeneration, increased dispossession, and an ever-widening gulf between rich and poor. Indeed, Caillebotte’s protagonists are explicitly the bourgeoisies, yet what is more interesting is that they are very likely the rural bourgeoisies. Beside the Place de Dublin was the newly constructed train station, the Gare Saint Lazare that took the rich residents of the country estates into Paris for a day trip of strolling through the new urban space built for their enjoyment.