Well Chucktx is right that there will be some transfer of heat through convection and there may be a slight drop in the temp. That said that same heat that can transfer through the fin while sitting, can also pick up radiant heat from the surrounding areas if such is higher. So you would not want to mount the cooler too close to say the exhaust. Generally though with most coolers, the slight decrease in temp while sitting still will not be enough to keep the oil from overheating if you do not move anymore than without.
Now while moving, they will drop the temp and 30 plus is not uncommon with a good cooler and sufficient air flowing. For most situation though it is not needed for these engines are designed to run at extreme oil temp with no problems. Key is to keep good oil to prevent a thermal break down and as well as adequate flow of the air.
There may be some areas of the country that an oil cooler would not be a bad idea, particularly the SW where summer temps keep easily exceed 100 plus routinely. For the vast majority it is not needed and even out west there are many that routinely go across the great deserts without oil coolers and have no issues.
Like mentioned before, it will not hurt and they do look cool (well some do), but I have seen more people have issues with them and especially when the temps are low than what they gain for the decrease in temp on the hotter days.
If one gets one, just keep in mind the low temps as well as the high. Get down around the 50's and it is a good chance the cooler is hurting you more than helping unless you regulate it via the a thermostat, a by-pass valve or like my good friend Chacha does, with a cover.
Now if one is like some and will not ride when the temps are in the low 50's, 40's or below, than you should not have that issues to be concerned with, then again you may miss the best ride out there!