The trouble with maxims, aphorisms and proverbs is that they often sound convincing, but it turns out that you can't rely on them in real life.

Even the Book Of Proverbs, which had the advantage of being not only produced by that byword for wisdom, King Solomon, but divinely inspired to boot, falls into this trap. "Pride goeth before destruction," it assures us in Chapter 16, "and an haughty spirit before a fall." If so, why are the corridors of power filled with bumptious mediocrities? Ecclesiastes is even worse, assuring us that the race is not to the swift, not the battle to the strong. Betting shops are full of poor people getting poorer as they test this contention, while bookmakers drive Bentleys.

This is particularly true of axioms warning us not to be misled by appearances. Beauty may be only skin deep, but most people's skin is still better looking than their intestines. Whether we ought to judge by appearances or not, the truth is that most of us do.

Politics, which has been described as showbusiness for ugly people (an aphorism which seems to have been devised by the Texan political lobbyist Bill Miller), is a sphere in which appearance and reality vie for dominance. But it's an unfair battle in which, pace Ecclesiastes, appearances are much stronger than convictions, arguments, ideologies and – all-too often – facts.

For all the analysis by political commentators and psephologists of the Government's current woes, this is the most pressing problem facing the Prime Minister. The recent series of blunders – mostly springing from the Budget, but also including the phantom fuel crisis and the mishandling of the NHS reforms in England – have damaged the Government's standing. But it is not just these measures in themselves which have led to the Conservatives' poor showing in the polls, but the fact that they reinforce a public perception. And that perception is easily summed up: most voters don't like the look of them.

Those who don't like the Tories don't like them, of course, because they look like Tories. At the same time, Tories don't like them because they aren't, in fact, doing many of the things that Conservative voters regard as priorities. At first sight, this looks contradictory, but both positions can be reconciled by observing that the leading members of the Government look out of touch.

Conservative voters may favour low taxes and a reduction of the state, but most of them are not millionaires themselves. When they look at David Cameron and George Osborne, they do not recognise people who share their problems or, more dangerously, their concerns.

There's not much the Prime Minister and the Chancellor can do about the first; it is hardly their fault that they happen to be much more privileged and rich than the vast majority of the population. But their failure to concentrate on the second – indeed, the impression which they give that they do not really understand the concerns of these voters – is a serious flaw.

The blame for this lies, for the most part, with Mr Osborne. It must be said that his looks and his manner are unfortunate; he has an air not only of entitlement but complacency about him. That may be terribly unfair (and no doubt we could all benefit from looking in the mirror ourselves), but the same cannot be said of his decisions, which appear even more damaging.

He is, after all, supposedly in charge not only of the Treasury, but of the electoral strategy of the Conservative Party. Some constraints have been imposed by the Liberal Democrats' involvement in the Coalition; it may account for the Tories' reluctance to address issues about the EU which are a central concern for many of their supporters. But most of Mr Osborne's choices have been his own, and even where they have been right – or at least defensible – they have too often looked out of touch.

Reducing the top rate of tax and freezing the additional tax allowances for pensioners may have been the right things to do, but it was grotesque to do them both at the same time, and through an inept attempt at subterfuge at that. The plans for removing child benefit have been slightly improved, but it made little sense to choose a 5% reduction in the top rate over further concessions there – especially when the basic rate threshold was actually altered, bringing millions more middle earners into the 40% bracket.

Capping tax relief on charitable donations is an absurd thing for any Conservative to suggest, particularly one in a Government which had as its big idea the "Big Society". Meanwhile, the Government has been too ready to back down on some measures (such as cutting free school milk and selling off forests) which would have caused little electoral damage.

The reality is that Mr Osborne's roles as principal strategist and chief tin-rattler for the Exchequer are fundamentally incompatible. And the electoral lunacy of some of his policies indicates that it is the second of those jobs which is guiding his decisions. The Treasury works on the basic assumption that government is about maximising revenue from tax, and that any money citizens manage to hang on to is somehow "lost" income.

Most voters, and certainly most potential Conservative voters, on the other hand, want to hang on to as much of their income as possible, because there isn't much of it to begin with, and because almost everything they buy – petrol, pasties, beer, stamps, houses – is taxed to the hilt as it is. In that sense, they don't differ greatly from the millionaires who try to minimise the amount they pay in tax, as Mr Osborne was "shocked" to discover last week.

In the important sense, however, they do – because the reduction in their income means that they have real difficulty in feeding, clothing and housing their families. Mr Osborne's strategy may be keeping the markets onside, and that is a real achievement, but unless he can show that he understands voters like these, he stands no chance of holding on to their support at the ballot box. As I've said before, it doesn't look good.