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1.
A type of shoe most commonly worn by punks, ska punks, goths, rockabillies, and pyschobillies. Brothel Creepers can often be seen on the feet of psychobilly bands. Brothel Creepers have a distinct crepe sole which can either be short and discreet or a platform-style.

Traditional Brothel Creepers are usually suede although they are now made of leather, fur, and other materials. Creepers can be styled to look like different types of shoes but maintain the distinct sole.
Stu Arkoff's Brothel Creepers are tough as hell.
by Hey There Guy June 07, 2011
 
2.
Footwear, generally of a formal design, that is donned prior to a night of debauchery (often in Amsterdam) ending in the bludgeoning of a pro. Can also describe any type of smart shoe, irrespective of afore mentioned bludgeon.
With a set brothel creepers on my feet and lust in my heart I took on the streets of the Amster-damager
by The Muck Miester General September 22, 2005