Good point. He didn't mention if he wants a bassier headphone and iem or if his preference is for something neutral. If $40 is the limit, and you want a closed headphone that is bassy, the JVCHAS600($30) is decent. The $10 JVC HAS160 is better balanced than the HAS600 with much better highs but not as much bass.
If you wany an open headphone, the Sennheiser PX100-ii(or ever better the original PX100 if you can find it) for $41. It is on the warm side, but has nice sound and good bass for an open headphone. The Koss Sportapro($25) is also warm sounding, however its bass is more muddy than the PX100-ii and it doesn't have as much detail. The Sportapro sounds almost the same as the Portapro, but loks different and is around half the price.
I can see why someone would want an iem and an open headphone or earphone, as isolation is not appropriate for all circumstances.