The hat is arguably the most potent accessory in a well-dressed man’s arsenal – it can make a persuasive or a regrettable impression. So, it’s important to get it right. Though the hat covers a man’s head, it also reveals his character. It should be worn with confidence. Wear it reluctantly or ambivalently and there’s the danger that the hat will wear you. Don’t be timid. The dressing landscape has evolved and there’s nothing to fear about striking out in the world in a hat that suits you.

The challenge, really, is to make the hat yours. Like velvet jackets and leather bags, a good hat looks better with age. Wear it in, wear it often and wear it until people associate you with it. Remember: wear something once and it’s novel, the second time it’s familiar, the third time it’s your signature.

Also consider your proportions. It won’t surprise you that big hats look better on big heads. As a devoted hat wearer, I prefer large, straight brims – they frame the face in a flattering way, drawing focus to the eyes.  

Don’t be afraid of idiosyncrasy, either – a good hat looks personal. My ragged Panama is missing its band, which makes the crown appear taller, and suits my rather large head. I wore the same beaten-up baseball hat every time I went fly-fishing for 10 years. It was there through triumphs and ones that got away. When I lost it in Yellowstone National Park, I was forlorn and convinced that it was responsible for me going fish-less the next two days. Yes, hats are powerful.

So let’s consider some classic hats and what they say about their wearers.

A natty hat, the fedora evokes classic style with a slight sense of raffishness. Traditionally, the brim turns gently down in the front and slightly up at the back. It’s survived some disagreeable associations with boy bands in T-shirts (we’re looking at you *NSYNC), and has remained a mark of distinction throughout the 20th century. Yes, the fedora endures – take it from no less an authority than pioneering journalist and author Mr Gay Talese. “I have been wearing fedoras since boyhood,” he says. “My father was a very stylish custom tailor, and he told me once: ‘No man is fully dressed without a hat’.” Mr Talese learnt this lesson well, and owns about 40 hats. He wears his fedoras with a suit and tie, and you would do well to follow his lead. Go forth with fortitude. As Mr Talese says, “Hats enhance one’s appearance. They add to (never detract from) one’s individual sense of style.”

Most men have worn a baseball cap at some time in their lives. Their ubiquity is hard to overlook, so when it comes to wearing one well, the safest upgrade to a baseball cap a man can make is to choose a woollen one. Lending it a slightly more sophisticated and, let’s face it, expensive feel, a wool cap (or a wool-flannel cap, which you’ll come across most often) is both suave and sporty, the smartening up of a classic. Wear it with a tailored wool coat or a knitted sweater in neutral, wintry colours like brown, navy and beige to keep it cosy-yet-collected.

The trapper hat has grown in popularity in recent seasons, and is recognisable by the way its flaps cover and warm the ears, making it a sensible choice for the chillier months. Originally inspired by the ushanka hats with fur flaps, a popular staple throughout Slavic fashion history (and perhaps most recognisably so when issued by the armed forces of the Soviet Union), the trapper hat is a more casual, less politically-charged version that looks rather up to date today. Trapper hats have been a key theme in Prada’s recent seasons, and channel a charmingly outdoorsy vibe that is versatile enough to pair nicely with, well, pretty much anything.

The beanie is a rugged, masculine hat, worn in the Navy, on the docks and by Mr Frank Serpico. In more recent times, you’ll find beanies in more elegant fabrics than their woolly predecessors, such as the cashmere offered by LA’s The Elder Statesman, and they remain popular even among those who’ve never wrestled with anything more demanding than the keyboard of a MacBook. And for good reason – it’s a hat that is as comforting as it is practical. “I started to wear a beanie when I was around eight, and red has always been my favourite colour,” says Mr Alexandre Mattiussi, the designer behind Paris-based brand AMI. A wool beanie is a versatile option: wear it with a cardigan or an unconstructed blazer.

The tweed flat cap once carried English hunting overtones, but it has migrated out of the country and looks good in nearly any setting. It has been worn by everybody from American newsboys (successfully) to the Norwegian curling team at the 2014 Winter Olympics (less so), as well as by men as diverse as Prince Charles and Mr Dennis Hopper. Men respond to the flat cap because it’s an elegant take on a sporting look, more elevated than a baseball cap but less formal than a fedora. London-based tailor Mr Shaka Maidoh of sartorial blog Art Comes First, a man of many hats, has been wearing flat caps since he was seven. “The first hat I ever remember owning as a kid was a flat cap my father got for me that I had to choose,” he recalls.

The trilby is a hat that has been around since the late 19th century and so has a classic element to it. Sir Sean Connery’s James Bond wore one with his Savile Row suits, and he looked dashing with a hint of playfulness. A more contemporary example of someone who wears it well is London hatmaker Mr Anthony La Touche, who is known as Mr Hat. He inherited both his first hat – a black rabbit fur-felt trilby – and then his love of hats generally from his grandfather. “He was never seen without a hat and now neither am I,” says Mr La Touche. A trilby leaves an impression, particularly with sharp, well-tailored jackets – this is the first port of call for those looking to add a hat to their formal or working wardrobe. A Larose grey trilby in particular would look perfect with a white linen suit jacket.