Ever since I was a little boy I have loved hats. A hat is an easy way to quickly change one’s appearance. Imagine you wear a three piece suit of mid gray Donegal tweed, a light blue check shirt, a wine wool tie and dark brown brogues and a stone coloured trench on top. The choice of headwear will give this basic combo very different meanings.

The most obvious hat to wear is some sort of soft brown trilby. This would the gentleman’s traditional choice. Formal with a relaxed air. A tweed hat would add an academic accent. Think of Harrison Ford in Indiana Jones. A black bowler hat is one of the more eccentric options and probably not a serious one for the majority of men. It would work though. How about a black beret as worn by the Basques? More arty than academic and even more unusual. But why not? Ernest Hemingway wore it during the civil war in Spain and he looked great in it.

How about a flat tweed cap? Or an eight piece cap? Each hat creates a different look. It can make you look adventurous, elegant, overdressed, ordinary and occasionally cool.

The result depends on the style you pick but also and probably more on the attitude of the wearer. A man must wear the hat, the hat shouldn’t wear the man. Some have no talent for this, they always look strange, no matter what hat they don. Others look great even with a tea cosy on their head. (This is not to say I recommend wear a tea cosy…)

Winston Churchill. He knew how to wear hats and caps. Barack Obama is less of a hat man while George W. Bush knew how to give a hat just the right angle. This is crucial. A hat has to have the right angle. Dean Martin was a master of expressing moods by giving his hat different angles.

If you love classic hats you’re probably not a winter guy. It’s impossible to find headgear that looks acceptable and keeps the ears warm at the same time. A man with his ears covered looks like a little boy who’s mother doesn’t want him to catch a cold.

That’s why I always keep the flaps of my fur cap up even if my ears turn to ice. Beauty is pain. Knitted caps are taboo for a gentleman too, unless he wants to become the butt of a fashion faux pas joke. Even the most handsome and debonair man will look stupid with a knitted wool cap on his head. And please don’t use the hood of your anorak or duffle coat, it would have a similar effect like a beanie. David Beckham may have a different opinion on the subject…but really, who cares?