IT has twice won the "Plook on a Plinth" award for terrible architecture, as well as the public vote in the Channel 4 series Demolition, which advocated flattening the entire town centre, describing it as the worst building in Britain.

The Book of Crap Towns lists it (after Hull) as the second-worst in the UK, but Craig Ferguson, who grew up there and now presents a chat show in America, thinks it's worse than John Prescott's stamping ground. What's it called? Cumbernauld.

You'd only have to be old enough to remember when Mr Ferguson was better known under the name Bing Hitler to recall this as the irritating slogan from advertisements for the place. But you would now have to be fairly old to remember when Cumbernauld was first designated a "new town" in the late 1950s, though most of the development, including the entirely enclosed town centre, came in the following decade.

In fairness to Cumbernauld, it is hardly alone amongst new towns in being regarded by many people as unlovely. Stevenage, East Kilbride, Irvine, Peterborough, Livingston, Basildon, Corby; none would be recommended as must-see destinations for a visitor to these islands. The very name of Milton Keynes, the design of which was much influenced by the theories of the Brutalist architects Anne and Peter Smithson, is a sort of shorthand joke for everything wrong with post-war architecture and planning, while the film-maker Stanley Kubrick selected Thamesmead, south-east of London, as the perfect setting for urban dystopia in A Clockwork Orange.

The future is rather more optimistically painted in Robin Crichton's 1970 film Cumbernauld: Town for Tomorrow, which celebrates the town on the basis of how meticulously it has been planned, down to the centralised crèche like something out of Moisei Ginzburg's Narkomfin building in Moscow. Yet it is precisely those carefully planned schemes which are at the root of what is wrong, not only with Cumbernauld, but dozens of other towns and cities.

Intoxicated by their brilliant separation of pedestrians from motor cars, it does not occur to the planners that the underpasses scattered around the town will become the natural habitat of drug dealers, muggers and rapists. As they plan the luxury penthouses which will rise above the shopping centre, they do not pause to ask whether anyone will dream of living in them. Or whether, like the characters in Gregory's Girl (filmed in Cumbernauld) they might instead fantasise about emigrating to Caracas.

Dazzled by the nakedly socialist principles of Brutalism, the planners and architects of post-war Britain merrily bulldozed tenements and terraces (the natural, human-scale, form of urban architecture), ran motorways through city centres and shoved arthritic pensioners and young mothers with prams up to the 28th floor.

Unfortunately, many of these exciting new buildings proved not to be very well built. To take one extreme example, Sir Basil Spence's tower blocks at Hutchesontown, an attempt to recreate Le Corbusier's glamorous, sun-drenched apartments from the south of France in the unpromising setting of the Gorbals, rapidly fell into disrepair and lasted less than three decades before being torn down.

Of course, there need be nothing necessarily or intrinsically awful about tower blocks or modern architecture in themselves. Some Brutalist buildings (Centrepoint and the Barbican in London, for instance) have wormed their way into the public's affections; the Park Hill estate in Sheffield is the largest listed building in Europe. But the poor reputation and state of repair of too many of these developments is, in fact, the product of their having been planned centrally, often by the state or local authorities.

The paradox of order is that it is much more likely to arise spontaneously than as the result of central planning and, as any evolutionary biologist will point out, millions of minor, random changes are more likely to result in perfectly successful adaptations, beauty and variety. The result of 70 years of careful planning in the Soviet Union after 1917 was a bankrupt state with a population enslaved (and routinely murdered) by their despotic overlords.

Not coincidentally, the Warsaw Pact countries also produced quite staggeringly ugly buildings. In fact, it is impossible not to see them as having been deliberately designed to be horrible, as a means of reminding their citizens of the contempt in which their rulers held them, to maximise their sense of oppression, and in order to amplify the misery of their everyday existence. If you go to Bratislava and stand outside the castle on the hill, you see, on one side of the Danube, the old town with its charming Mittel-European houses and cafés, its winding streets, its handsome cathedral. On the other bank, as far as the eye can see, there is a forest of hideous Stalinist concrete blocks.

One part of the city is the result of thousands of individual decisions by builders, architects, homeowners and shop-keepers. The other is the result of planning. And it is precisely because it is an indisputable fact about human beings that we make mistakes and cannot know everything that order and harmony are more likely to emerge without a centralised grand design.

Any centrally designed scheme may work, but human fallibility being what it is, it is more likely that it will not. But when many different ideas are presented, the competition between them is more likely to lead to a successful outcome. This is the basis on which scientific knowledge advances; it is the means by which free societies evolve; it is the principle which guarantees each member of society liberty and autonomy.

A Cumbernauld which had grown spontaneously from the decisions of those who lived in it would almost certainly be a less homogeneous place. It would probably have quite a few bad buildings and oddities in its layout. But it would also have many more things to delight and enrich its citizens.

It wouldn't be a new town, of course; it would just be a town. But it's because the planners of the new towns set out to create exemplary towns that most people prefer to live in towns and cities that were planned – to the extent they were planned at all – over centuries, by their residents.