The Balenciaga City bag, originally known as the Motorcycle bag, is the cornerstone of the brand's modern handbag legacy. Designed by Nicolas Ghesquière in 2001, its slouchy, unstructured silhouette and tough hardware were a radical departure from the rigid, ladylike bags of the era. Rejected by executives for its distressed look, only 25 prototypes were made before Kate Moss famously claimed one and made it an icon. Today, the City bag remains a symbol of early 2000s grunge and is more coveted than ever.

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