How to wear a hat (without looking like an idiot)

lots of hats in different colours

There’s a hat for everyone out there somewhere.
Image source: Joshua Coleman

It’s not quite the heyday of the 1950s, when hats were just as common as coats and good manners, but those classic hat styles are becoming increasingly popular with today’s fashion-conscious men.

Whether you’ve always been a hat man or you’re a little nervous about doing the hat thing, read on, as this blog will clue you up on a few hat-wearing tips. Hint, it’s all about choosing a hat that suits you and wearing it with confidence.

Suits you, Sir

man in hat tying strawberries

The key is to find the right hat for you.
Image source: Anna Jurkovska

Straight up, some people look awkward wearing a hat. And that’s usually because it’s the wrong type of hat for the man. Every man has a hat that suits him, and the key to your personal hat happiness is finding the right type of hat to suit your facial structure. The Art of Manliness blog explains:

“All hats make a man look more dapper. But picking a hat that is right for your face shape will increase your attractiveness and give you a sharper appearance.”

Check out our complete guide to hats to find out what suits your face shape and more.

Know thy hat!

man by fountain wearing a hat

A well chosen hat can be the crowning glory of an outfit.
Image source: Samuel Windsor

Hat anatomy: Know your crown from your rim from your pinch and get familiar with the anatomy of a hat by visiting the He Spoke Style blog. As blogger Brian says, “no accessory has the ability to change up a look or silhouette quite like a hat,” so it’s worth learning how to make it work for you and your mug!

Material: Proper good quality hats like fedoras, homburgs and the other usual suspects are generally made from felt with a silk lining. Felt hats are normally winter hats and will keep your head dry and warm in the winter. Summer hats like the Panama and boater are traditionally made from straw and, depending on the weave, can be either floppy and flexible or hard and firm.

Fitting: Hats come in all manner of shapes and sizes so make sure yours fits well, with the brim resting on your ears. It should sit firmly on your head and be able to resist a gust of wind, but it shouldn’t stop the blood circulation to your brain! Hat sizes are either measured in S/M/L or traditionally as numbers, so it helps if you have an idea of your head size beforehand, unless you’re buying from a hat shop where they will measure you up good and proper.

How to choose a hat

Straw is for summer and felt is for winter, but really it’s about the look. The Fashion Beans blog says, “Just wear your hat with confidence, that’s the real key,” and fires off some of the most popular hat styles for the summer, so feel free to browse their suggestions. Let’s look at some of the most popular styles.

Trilby & fedoras

mon in rusty car that clearly doesn't work wearing a trilby hat

A good quality trilby is a trendy option if worn well.
Featured product: Trilby in Biscuit

Popular styles that have been around since the 1890s. Both have remained popular, especially the trilby, which has adorned iconic figures such as Frank Sinatra, Indiana Jones and mob gangsters. But do be careful with the trilby, as it has become over-popularised and can sometimes come across as tacky, especially if it’s a cheap version. Noah Brand writes on The Good Men project:

“Trilbies, using less material and being more forgiving of poor fabric, are cheap to make and thus have become widely available. So on one level, a guy in a cheap trilby is saying “I wanted a hat so I just grabbed the first one I saw and considered that sufficient.” Worse, though, the simple fact is that trilbies look like c**p on most men. They’re unflattering and unattractive.”

On that note, the fedora is perhaps the better choice.

Flat cap

man by car in hat

A flat cap is a good option for country walks.
Image source: Samuel Windsor

The flat cap is a safe bet. Historically associated with the working classes, “variations of the flat cap date back centuries, when wool was the backbone of the English economy,” as discussed in the Not Yet Published blog post dedicated to the history of the hat. The peak can be arched and vary in size, and the area at the top of the head can be tight-fitting or looser; both styles are popular and this hat can work well with a range of informal outfits.

Bowler hat

man hold hat

You’ll need confidence to pull off this classic look.
Image source: LoloStock

Fans of James Bond will remember the menacing Oddjob and his deadly bowler hat. The classic bowler hat is sturdy with real character, and it carries true prestige in the hat kingdom. It can be tricky to pull off (both physically and aesthetically) so it requires confidence, but it can look great if it suits your face shape and you feel comfortable wearing it.

Pork pie hat

pork pie hat

Pick a pork pie for a distinctive look.
Image source: KDS444

Though it bears little resemblance to its culinary namesake, it’s a stylish option for a stylish gent. It’s practical and distinctive and has gained in popularity after being the hat of choice for Heisenberg of Breaking Bad.

Panama hat

Panama hat rum and ashtray

The Panama hat is the perfect summer style for any gentleman.
Image source: Shutterstock

A popular choice with the mature gentleman. It’s soft, durable and flexible, yet light and breathable, which is why it’s a perfect hat for the summer. And, for the record, the Panama hat wasn’t actually invented or even made in Panama, but rather in Ecuador. The name ‘Panama’ was adopted because that was the country to which most of these hats were exported. Finish off the sophisticated look with a relaxed linen suit, ideally on your own private yacht.

Building your confidence

Find the hat that suits you and that you like and then go for it! If you’re still a little unsure about venturing out, a brilliant way to build your confidence is to attend hat-friendly events (where everybody is wearing them). Think weddings, fancy dress parties, race meets and so forth.

Hungry for more hat knowledge? Take a look at our visual guide to men’s hats here.

Posted in How To - Style.