We happen to think Jays' q-Jays are probably the most comfortable earphones we've ever worn. Their tiny enclosures and super-soft silicon tips make them almost completely unnoticeable, with nothing physically there to even risk causing discomfort. They're also excellent earphones to boot, with twin drivers in each ear.
Sennheiser's CX 500s also boast small enclosures and silicon tips, which contribute to their comfort. Nearly as ear-friendly as the Jays, they have the advantage of being much more affordable to the casual music fan and more substantial for those people repeatedly finding themselves breaking things they own.
Enclosure-wise, Etymotic's ER-6i earphones are exceptionally small, and their terrific triple flange silicon tips are as soft as a kitten's underbelly. While extremely comfortable, some people may find the tips intrusive, but they're worth persevering with if you want accurate sound and lightweight comfort.
Finally, Creative's Zen Aurvana -- nice, lightweight earphones and decent sound, decent price and comfortable silicon tips to boot. They're great all-rounders in many respects, though sonically they're inferior to the Etymotic or Jays alternatives. Their larger enclosures are particularly good for people with larger ears.
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