Sennheiser PX100 continues to be my preferred portable headphone. The PX100 is sort of like like a cheap, portable Grado SR225.
Full-size open cans: Sennheiser HD595 when low impedance is required or HD580 when it's not. Some say the HD595 is the Grado of the Sennheiser range. It is not. If you love Grado, you probably won't like the HD595 any more than any other Sennheiser product. It is really not much like a Grado at all, although I do agree the soundstage seems a bit closer than with other Senns, so in that aspect it is vaguely Grado-like. If you're after a really good all-rounder that is comfortable, non-fatiguing, and tolerant of a wide variety of consumer sources and headphone outputs, the 595 is a great way to go. But you gotta let it burn in. A lot.
FWIW, I've owned a variety of Senns, AKGs, and Grados.
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