If the cap fits, wear it. But not if your name is William Hague

While fashion felons may find themselves regularly hauled up in front of the Style Council for their crimes, it isn't usually for a repeat offence. But William Hague's ill-judged flirtation with yet another baseball cap made for a sartorial trial, as pictures emerged of him wearing the accessory that famously lost him not only his street cred but also an election.

A 1997 publicity stunt, when Hague wore a similar hat emblazoned with his name while riding the log flume, was generally credited as destroying any chance he had of leading the Tories back into government. Now they're in power again and pictures have emerged of Hague once more sailing perilously close to ridicule. What was he doing, roaming Central London in such apparel? Perhaps he's one of those neurotic hand-wringers who get anxious when things are going too well.

But he doesn't look fazed by his choice of headgear, does he? William Hague is practically glowing in this Italian Riviera ensemble. From the loosely belted and low-slung jeans (in faded black, rather than a more modish indigo) to the long-sleeved T-shirt that he has carefully tucked in (summoning memories of his predecessor John Major's supposed penchant for firmly anchoring his shirts into his underpants), he is every inch the urbane modern gentleman – and just the sort that belongs in Casual Cameron's Cabinet.

Except Hague doesn't quite pull it off. It's obvious what he's done here: seen the Prime Minister in similar a laidback, louche outfit and thought, 'I can do that; I'm too hot in this suit, and I can do off-duty as well as the next man.' What he failed to realise is that relaxed leisurewear only looks good if you're posh. Just as he failed to look as chic as Princess Di on the flume, so he has fallen in the wake of shirtsleeves Dave and his Eton brand of sports casual.

Pundits will point out that the cap itself is a little tight-fitting, following too closely the lines of Hague's signature glabrous head. Pedants will note that he has plumped for one that looks like it might have come free with a car-valeting kit. (Rule of thumb: if a logo must be involved, at least opt for the most bling.) Purists may flag up the fact that Hague has hand-bent his cap's peak, like we all used to in the late Nineties to give it that worn look; the baseball cap kings of today leave theirs straight as a dye and let the item sit atop their heads rather than ramming it on, as if it might blow away at any minute. Nonchalant, innit.

But style quibbles aside, this hat speaks of classical tragedy. Hague's hamartia if you will – his fatal flaw – is his inexorable draw to the baseball cap. He narrowly escaped the wrath of the gods once before, but it's bare-faced hubris to wheel one out again. Will it be the source of his downfall?

Let that be a lesson for...

Conrad Black

When the former media magnate dressed as power-hungry Renaissance wheeler-dealer Cardinal Richelieu for Freddie Windsor's birthday in 2000, some cracked jokes at the apposite nature of his costume. After a stint in jail for fraud, Black would do better styling himself after The Man in the Iron Mask.

Elton John

Nothing screams excess like impersonating the Sun King on your 50th birthday. It wasn't enough for the singer, though, who also added a five-foot pompadour to the mix. His costume was so large he had to travel to his own party in the back of a removal van.

Andrew Neil

If life is already too Versailles for your own liking, why not try a bit of downwards convergence in the now-infamous manner of Neil. The only reason he gets away with a baseball cap (if you're reading, William) is because the vest diverts attention from it.