In general, the optimum length of wire is going to be significantly longer than 1/4 wavelength. The system ends up being an OCF dipole-ish structure with typically your hand acting as an inadequate counterpoise.
Antennas for hand-helds are (or at least should be) designed with this in mind, which is why the "tiger tails" as often do nothing or even degrade performance by detuning, as often as they may help.
Some of the crappy chinese replacement antennas I once checked out apparently didn't understand this issue, and were tuned to the HT's operating frequency (some were even higher up into the business bands above the ham bands) - when they should have been tuned somewhat lower. That was why they had poorer link performance than even the shorter (but correctly tuned) stock unit that came with the radio.