A market-based labeling system and method provides tools to assist a user in accurately generating labels. The system includes a processor-based device, such as a computer, that has associated input/output devices, such as a keyboard and a display. The processor-based device also includes a user-friendly labeling application, which may be implemented as a set of instructions to be executed by the processor. The labeling application may guide the user through a series of steps to produce a set of labels. The labeling application preferably generates the user interfaces and a file that may be viewed, edited, saved and/or printed on an associated printer. The labeling application may include one or more modules, each module being geared toward labels for a particular market. This labeling application tool may run on a general purpose processor, such as a computer, and may interface with general purpose labeling software. Alternatively, the labeling application tool may be embedded in a labeling device, such as a portable hand-held printer. Also, methods are provided for quickly and accurately generating labels by adapting a labeling application tool to the user and the user's market. For example, one method allows a user to select between a guided, interview-type process for identifying labeling requirements and a user-directed process for identifying labeling requirements. The methods may be implemented in software.