Depends on my ear capabilities. If I don't need noises from outside clearly or sensitive to higher dB (big speakers or TOA speakers), IEM would be choices. But for home job both multimedia and radio hunting, headphone is always the best (the wired one, not the portable).

IEM.

Aside from the obvious sound quality on its price, Certain modules like cables, or even the speaker itself is actually replacable. Also it's easy to put it on pocket / bag too.