How to wear men’s hats

With a few simple rules, finding the right hat is easier than you think

With a few simple rules, finding the right hat is easier than you think
Image source: Aleksandra Belinskaya

Looking great in a hat is actually very simple. Not sure how to choose one that suits you? Here’s our advice for getting the best style of hat for your face shape, stature and features.

Which hat suits me best?

Navy blue cotton Ambassador hat from Samuel Windsor

A well chosen hat can be practical and stylish
Image source: Navy blue cotton Ambassador hat from Samuel Windsor

A few quick and easy rules will help narrow the field:

  • Large men with big heads look best in taller peaks and wider brims.
  • A downturned brim suits a tall man, while an upturned brim is better for the shorter man.
  • If you’re slim, avoid very wide brims.
  • Very tall? Avoid hats with very high peaks.
  • A wider brim suits men with larger facial features because it balances your proportions.
  • Angular features? A similarly sharp trilby is the way to go.

Here’s everything you need to know about the different hats available, and how to wear them.

How to wear a trilby

This summer-weight trilby from Samuel Windsor is made from the finest linen

This summer-weight trilby is made from the finest linen
Image source: Trilby hats from Samuel Windsor

For winter wear, pair your trilby with a casual tweed blazer, shirt and cords. Or dress it down with straight cut jeans, a t-shirt and bomber jacket. This hat suits all but the biggest guys, but it looks particularly good on those of medium height with fairly regular features. The trilby has never quite lost its hip two tone/ska connotations and also looks great with smart trousers, jeans or chinos.

During the summer months, try a trilby in Irish linen rather than wool. This version is ideal for providing shade from the sun while simultaneously allowing the air to circulate. A pair of summer weight chinos, a striped polo shirt and classic wayfarer sunglasses completes the look.

How to wear a pork pie hat

The top of a pork pie hat resembles that of the famous Melton Mowbray pie

The top of a pork pie hat resembles that of the famous Melton Mowbray pie
Image source: Cornelius Krishna

Wear a pork pie hat with a smart blazer, a preppy button-down collar shirt, and chinos. Or for a more casual take, wear it with straight cut jeans, t-shirt, and a casual cardigan. And don’t forget your shoes – for smart casual occasions, this hat deserves a decent pair of wingtip brogues at the very least, or, for a true taste of dapper, go for tasselled loafers. Dressing down? A pair of suede brogues is all you need.

With its narrow round brim and short “telescopic” peak, a pork pie hat is one to avoid if you have a round or short face – in which case you need a hat with a higher peak and wider brim – a fedora perhaps. Otherwise, this hat is a great way to make a statement.

How to wear a bowler hat

A bowler hat is a smart option for the man about town

A smart hat for the man about town
Image source: John Gomez

Think of your bowler hat as an alternative to a trilby or fedora and wear it with a blazer, or in the colder months, your covert or cashmere coat. A smart hat for the busy man about town, your bowler is an understated asset which, by virtue of the fact that not that many men care to wear one these days, will see you stand out from the crowd for your elegance and sophistication.

The bowler hat is a versatile piece of headgear that suits men with a range of face shapes – the only guys who should probably avoid them are those with particularly round faces. If that’s you, you’ll look better sporting a fedora.

How to wear a flat cap

Flat caps from Samuel Windsor are available in tweed, cotton, linen and cool microfibre depending on the season

Flat caps are available in tweed, cotton, linen and cool microfibre depending on the season
Image source: Flat caps from Samuel Windsor

Wear your flat cap with jeans, a plain t-shirt and Harrington jacket with a smart pair of brogues or Chelsea boots on your feet. Want to take it up a notch? Moleskins, Tattersall shirt, summer weight tweed jacket and a flat cap makes for an excellent smart casual ensemble.

Flat caps suit most men as long as your head isn’t too narrow, or too large, in which case you need either something rounder or something a little better proportioned – perhaps a fedora which, if you also have quite a round face, will help give your shape some angles.

Did you think flat caps were just for winter? While winter weight tweed might indeed bake your head on a hot summer day, try the same style in lightweight microfibre or linen and you’re onto a winner.

Why everyone can wear a Panama hat

Handmade Genuine Panama hat from Samuel Windsor

The Panama hat can be folded and snapped back into shape for ease of travel
Image source: Handmade Genuine Panama hat from Samuel Windsor

Wear your Panama hat with brogues, chinos, and a long sleeve cashmere polo, or slip on an unstructured jacket to bring the look into the evening. Equally at home with a summer wedding suit or a pair of simple chino shorts, a Panama hat is a smart option whenever the sun comes out to play.

A genuine Panama hat handwoven in Ecuador is a fine thing indeed. Not only does its foldability make it the ideal companion for holidays and cruises, it’s one of the most stylish and versatile hats a man can own. A medium peak and brim make this hat suitable for all builds, face shapes and statures. The all-rounder of men’s summer hats – reach for yours whenever it’s hot enough to crack out your linen jacket.

What is an Ambassador hat?

An Ambassador hat from Samuel Windsor beautifully complements a linen suit

An Ambassador hat beautifully complements a linen suit
Image source: Hats from Samuel Windsor

While Jerome Bowes was British ambassador to Russia in 1583, Czar Ivan IV punished the French ambassador for failing to remove his hat in his presence by having the hat nailed to the poor man’s head. Faced with the same threat, Bowes told the Russian to get lost because the invincible Queen of England bares her head to nobody.

Who knows whether Ambassador Bowes was the diplomat who inspired the hat, but regardless, this piece of summer headgear is certainly worthy of his title. Featuring a downturned brim, an ambassador hat is ideal if you’re on the tall side, and you’ll also be delighted to hear that it comes in a range of colours, all offset by a snazzy contrasting ribbon. Wear your Ambassador hat as per the Panama.

How to wear an adventurer hat

A Linen Safari hat from Samuel Windsor is ideal for hot weather

A linen safari hat is perfect for very hot weather
Image source: Linen Safari hat from Samuel Windsor

Wear your adventurer hat with moleskins and a check shirt for a casual look that’s suitable for most occasions. Outdoorsy? This is the hat for you. Made from 100% wool – an excellent insulator – this wide brimmed adventurer hat keeps the sun out of your eyes, and protects your ears and the back of your neck. Ideal if you love angling, walking or gardening, this is a practical and stylish hat designed for those who like to keep active.

Venturing to warmer climes? A linen safari hat gives you the same look but keeps your head cooler. Add chinos or linen trousers, slip on a summer print shirt and you’re ready for any eventuality.

How best to wear a straw boater

Always wear a straw boater hat at a jaunty angle

Always wear a straw boater hat at a jaunty angle
Image source: PiercarloAbate

A specialist hat for special occasions, a straw boater hat is the perfect apparel for those sunny summer regattas – if you’re going to wear a boating blazer, you’ll need the straw boater hat to complete the look.

Fashion historian Colin McDowell describes the boater as “a jaunty, cheeky upstart of a style, never to be taken too seriously” in his book Hats: style, status and glamour (1992). But how do you wear it? According to McDowell, a boater hat should definitely be worn at a rakish angle.”

If you’re planning to punt your partner along the river or attend the annual village fete this summer, a straw boater is the perfect way to make a splash and have a bit of fun.

What’s your favourite hat? We’d love to hear from you. Leave a comment below or pop over to our Facebook page. 

Posted in How To - Style.