Look at monitors the size you are considering in a store. Consider how far away you'll be sitting from the monitor and what feels comfortable for you. 27" may be fine for you, but it might also seem a little too wide, at least at first.
On the other hand, if you're going from a 20" squarish monitor to a 24" widescreen, you may miss the vertical space of the 20" even though you have more horizontal space. So you just have to look at the monitors and judge for yourself.