Conventional portable audio systems often include a pair of headphones that are connected to a media player (e.g., by one or more wires or by wireless technology). It is increasingly common for users to use portable audio systems when engaging in outdoor activities. While the media player in any given portable audio system can be used in a variety of settings, it is often the case that the headphones employed are not as versatile. For example, in-ear headphones may provide for portability, but such headphones may provide poor audio quality, be uncomfortable, or both. Where multiple wires are used to connect the headphone speakers to the media player, each additional connection (e.g., each connection between male and female audio jacks) may further degrade audio quality. While larger, over-the-ear headphones may be more comfortable, they may be awkward to wear with outdoor gear, such as goggles. For example, it is increasingly common for outdoor enthusiasts, such as skiers and snowboarders, to use portable audio systems when engaging in outdoor activities, such as skiing and snowboarding. In most cases, skiers and snowboarders favor smaller, in-ear style headphones because helmets, ski goggles, ear protectors, hoods, and headbands can more easily be worn over such headphones.