The phrase refers to attire designed to resemble the stereotypical clothing associated with pimps, often worn for celebratory events occurring on or around October 31st. These ensembles typically include flamboyant and exaggerated elements such as brightly colored suits, faux fur coats, large hats, and ostentatious jewelry. An example would be an individual sporting a purple velvet suit with leopard print accents, paired with a cane and a wide-brimmed hat adorned with feathers.
The adoption of such costuming, especially for Halloween, raises questions about cultural appropriation and the perpetuation of harmful stereotypes. While some view it as harmless fun, others see it as trivializing the exploitation and suffering connected to the sex industry. The history of these stereotypical representations often stems from media portrayals and can lack sensitivity towards the realities of those affected by pimping and sex trafficking.