A lesson in what not to wear when you're on holiday

Successful women are forever judged on their appearance. So why shouldn't men suffer the same fate, asks Harriet Walker

There aren't many scenarios in which middle class, middle-aged white men come under scrutiny for their wardrobe choices; we're normally more interested in the skeletons they're keeping in there than the clothes. But come holiday season the doors are flung open and the contents exposed to global ridicule. And why not, given that their female counterparts put up with it every day?

Christine Lagarde was recently described at as the "world's sexiest woman" before anyone considered whether she might also be the most-powerful, and the likes of MPs Gloria del Piero and Luciana Berger have been dubbed "the Milibabes" by the tabloid press. Cheryl Cole's trials and tribulations this year have been measured by her haircuts, rather than her output, while Simon Cowell's quest for world domination goes ahead regardless of how high his waistband creeps.

So it seems only fair to haul David Cameron and George Osborne over the coals as they debut their holiday looks this week.

First up: Mr Osborne, whose excuses about the economic shortfall are so manifold it looks like he had to go buy some extra-roomy trousers to keep them all in. His loose-fitting, low-slung jeans are not quite the type that Barack Obama railed against (that belt below the buttocks, resembling nothing so much as a sling with two eggs in it) but they're certainly more "rad" than a man in his position should admit to being.

Clearly aware of the dangers of being seen to be too street, Osborne has tried to up the formality by teaming these with a blazer and shirt. Like a child surreptitiously peeing in a swimming pool, he thinks that if the top half looks nonchalant, no one will notice what's going on below. But those hybrid trainer-shoes are nothing short of remarkable – they're the footwear equivalent of the Third Way: a practical and directional sole smothered by traditional uppers that will keep the masses happy.

And his bag! Is it a rucksack stolen from a child? For a man so happy wielding the fiscal razor against the nation's bared throat, it looks a bit, well, namby.

At least the ever-suave Prime Minister hasn't made any mistakes. How admiring everyone was when he wore Boden on the beach and Gordon wore a suit. What could be more indicative that he was in touch not only with the common man, but also with his feminine side? How we loved him for it. That was before he stiffed just about everyone apart from Rupert Murdoch, so it behoves us these days to point out that he's wearing no socks. And that makes him a weirdo.

There's a time and a place for "mankles", fashion's latest neologism, and Cameron has got them both right. What he has failed to realise is that it's just not the same when the loafers look like ones your uncle might own and the trousers are the ones you wear to work. He looks like he's stolen someone else's clothes, and voters might readily believe he had, but for the blue shirt which accompanies the Camerons on every holiday they take.But the nadir of the "white man on holiday wardrobe" is, without doubt, Peter Stringfellow's eponymous beach-garb – it was a string for his fellows. But while we may mock the attempts by politicians to normalise through casualwear, there's something to be said for the flauntings that the likes of Stringfellow, Simon Cowell and retail magnate Sir Philip Green engage in. It's the opposite of a Samson complex: these tycoons are so successful that their physique just doesn't matter, and neither does clothing it.