A configurable audio system for use in a plurality of different settings includes a set of speaker assemblies that can be attached, detached and reattached to a plurality of different accessories configured for use in specific settings (e.g., ski goggles, or conventional headphones). In one implementation, each accessory comprises a set of engagement assemblies for detachably receiving the set of speaker assemblies. For example, a strap on a pair of goggles can comprise a set of engagement assemblies affixed in-line with the strap. By contrast, a traditional headphone band can comprise a pair of engagement assemblies that extend from each opposing end of the traditional headphone band. In either case, each engagement assembly of the goggle strap or the traditional headphone band is configured in size and shape to attach to, and detach from, each speaker assembly, as desired.