We should be skeptical of a belief given by common presuppositions in the case that they can be explained by some reason other than their veracity. If we can explain how a habit forms (say, the belief in external objects, that historical events are actual, or within a given religious context that certain dispositions are sinful and that we have an innate conscience) and give an adequate account of how it comes to be, why do we need to assume that it also gives us a direct window on reality? Belief in external objects comes about in early stages of development as we learn to deal with the bloomin' buzz and confusion around us, to organize it so that we can make sense of it. It it a very practical habit to believe that our blankie is still existent when it is put behind the pillow, even though we cannot see it.
Reality is such that the belief is practical. But this does not mean that reality is as the belief holds. I see a green leaf; the leaf itself is not green (at least while I'm taking off my idealist hat for a moment and speaking from the perspective of the realist), but is a physical object that reflects the light of a given wavelength such that it hits my eye, where due to a complex interaction of rods and cones and processing in the LGN followed by assimilation in the visual cortex I experience the qualitative experience of green on a leaf shape. The belief that the leaf is green is not caused by the leaf's actually being green, though the reality is such to produce that belief, produce it regularly, and make it a helpful belief for navigating the world. Similarly, belief in external objects can be caused by some feature of the world that is not the actual existence of external objects.
But if this is the case, why believe that there are actually external objects? I have explained why there is a wide-spread habit pertaining to them (and there is the experimental data to further substantiate my claims), and there does not appear to me at this point to be anything left unexplained. So why do we assume some mystical sense which gives us real knowledge of the way things are? There is no facet of our experience otherwise unexplained which needs such a faculty. Therefore, positing such a faculty is arbitrary, merely a means of allowing us to hold to the same things we have always held instead of actually trying to think through them and explain them. There is as little reason to assume that faculties of this sort exist, as that a misargued mathematical theorem gives us probable mathematical knowledge. But if such a belief only arises from practical engagement in the world, then it is hard to see without further argument how it could even possibly have metaphysical value unless as merely a different dimension of the same world.
There is a positive side to this, though. While it seems utterly arbitrary to multiply entities beyond what is needed for explanation (not that the simplest theory must be true, but that whatever is posited must play some explanatory role not otherwise accounted for in order to have any meaning), if we avoid doing such, then typical skeptical arguments melt away. Take Hume, for instance: Hume doubts causation, as to whether it is anything more than constant conjunction, but then returns to billiards where natural impulses make him believe in causation again. On my view (which likely is a repetition of the work of others who have explored this much more deeply), Hume isn't merely caused by natural impulses to believe in causation and so engage in self-deception. The language of causation is rooted in empirical life as a way of organizing it. Talk of one billiard ball causing another to move is perfectly legitimate; when we are talking about causation in billiards, we are not referring to features such as necessity, or universality, or quantum mechanics. We are explaining that aspect of our experience which involves the balls hitting each other regularly, enabling us to play the game, without thought of what might be causing this; there is continuity in practical discussions of causation even as philosophy and science radically change our understanding of it. To self-reflectively talk about causation is to enter into another context, and in this context causation as a general principle may be doubted, and may even be meaningless, but this self-reflection is not a feature of most everyday accounts of causation. This philosophical context is not illegitimate, but its concerns are not the concerns of the billiard player, and its accounts of causation get at something else. Now, for the philosophical billiard player, these two accounts may be entangled, or one may take priority; it depends on the specific context and the specific person, but there is nothing that says that different language games are hermetically sealed from each other.
Let us take Descartes as well. Descartes postulates an evil genius which could be messing with his mind. On my view, this is irrelevant. Concepts are taken from experience and explain experience. If that experience is of an evil genius messing with us, whether we know it or not, then these concepts explain that experience of human-nature-being-messed-with. They are concepts forged from inconsistent memories or other tricks which are thrown our way, but this does not make them false; they merely describe a rockier terrain than one in which we would have perfect memories and veridical habits. Similarly, if we were in the Matrix, our concepts would describe the world of the Matrix, again whether we would realize we were in it or not. It would be the world of our experience, and thus what concepts would arise from and refer to.
I do not mean by our "experience" merely the world of sense-data, but absolutely anything experienced. Consciousness, imagination, and our conceptual life seem to be legitimate realms of experience as well. If there is some Agent Intellect beaming intelligibles into our minds, then this is a part of our experience. The worlds of the poet are just as much experienced, even in the wildest cases. Skepticism isn't about strictly rationing our intellectual diet; it is about clearing away sedimentations and ossifications which obstruct living.