My hair is thinning (some would put that in the past tense). On a cold day, I need a hat.
Plus, wearing a hat is a much more practical way of keeping off the rain than an umbrella. Take a look at any 1930s Hollywood film that features rain and you will find almost all men sheltering by turning up the collar of their coat. A waterproof coat with a high collar, combined with a hat, is very good at keeping out the rain. You don’t need to carry around a cumbersome brolly and your shoes are drier.
Modern man has an irrational aversion to getting anything wet, even if it is a coat designed for that purpose. Take a hat out next time it’s raining, rather than an umbrella.
So I need a hat, and hats are good. But what are my options? A Fedora, Trilby or other rimmed hat is terribly hard to pull off, particularly when you are on the young side of 40. I think it comes after cigars but before pocket watches in the order of accessories you can get away with as you get older. A beanie makes me look like a teenager. And a baseball cap makes me look like an American freshman.
(I think this lack of reasonable headgear is one reason for the huge turnover in umbrellas. People buy disposable umbrellas because they don’t really want one that is bulky to carry around, or they are afraid of losing. But they have no alternative against the rain because they feel silly in a hat. So we’re doomed to drown in crap brollies.)
A flat cap is the only realistic headgear for those between 21 and 40. It was this necessity that first persuaded me to buy one. But over time I have also learnt lessons about their suitability and propriety. Here, material is key.
A flat cap need not necessarily look like country headgear. It does if it is made of tweed or thick wool in hound’s tooth – even more so if it has large checks on it in bright patterns. As Winston rightly points out, Lock & Co does some marvellous caps, but they are deliberately items of countrywear: they are casual option for a man that already wears a Fedora or other rimmed hat for work. They are deliberately sporty to contrast with the formal brims of the working week.
We are not in that position, and do not need checks or tweed as a result. Instead, I recommend going for corduroy or felt. Both look smoother and smarter. Plus, ape the colours and (lack of) patterns seen on formal headwear: black, grey and occasionally brown.
If you wear a tweed flat cap with a suit you look like an Irish farmer on his way into town. If you wear a smart, black felt hat with a suit (and black shoes, obviously) it is merely your take on a staple formal headwear.