Men’s hats are a surprisingly challenging conundrum even for the most fashion-forward fella. Indeed, while peripheral areas like shoes and watches offer a variety of acceptable options, it’s usually a mere hat or two that can fashionably top off a given outfit. There are so many to choose from, you might find yourself spoilt for choice. The key is knowing which caps for men go with each outfit, something easier said than done. Are we being a little hyperbolic? Perhaps. On the other hand, we’d rather you proceed with caution than rock the wrong style of men’s hat and look the fool.

We’ve compiled a guide to wearing different types of men’s hats. Including a breakdown of the anatomy of a hat. Discover how a cool hat can perfectly enhance your style with our guide to the 13 Types of Men’s Hats for Any Occasion

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The Anatomy of a Hat
Every part of a hat has its purpose. This purpose could be solely for aesthetic reasons, comfort, or pure function. One thing is for sure, who would’ve thought you could get this up close and personal with a hat? The thing is, buying a lid is like telling your barber how to cut your hair. It can be a scary experience at first, but once you understand the general idea it becomes a walk in the park. Understanding the anatomy of the hat is the first step. We’ve got a list of key hat terms and illustrations as provided by Stetson to help make that first purchase as smooth as the silk.



Essentially the body of the hat. The crown is the central dome which extends upward from the outside brim. The crown surrounds the wearers head primarily for the purpose of style.



The brim is defined as the protruding horizontal edge of the hat. It makes its way around the bottom edge of the crown and extends outwards on a horizontal axis. In a similar way to the crown, you will find there are many different styles of brim to choose from. You will find cowboy-style curved brims from the brands like Stetson, and brims that are both long and short. The brim is a combination of both style and function, it is mainly used for sun protection.

Pinch or Dents

Pinch/ Dents

The pinch points or dents are part of the design of the crown. While they’re primarily for style purposes today, their origin lies in function. The pinch point makes taking the hat on and off much cleaner and easier. If you’re the ultimate gentleman, the pinch point will make tipping your fedora even easier.

Liner Tipping

Liner Tipping

The interior fabric of the hat. This is a trademark feature of many hats, including high-quality examples from the likes of Stetson. The liner tipping is found on the inside of the crown, and sometimes features the brand’s logo or a pop of colour.

Edge Binding

Edge Binding

The edge binding is the trim that surrounds the brim. The binding is usually made out of quality material for either style or functional purposes depending on the type of hat.



This part of the hat anatomy is like a pinch on top of the crown. As such, the crease is used for the same reasons as the pinch. This means, its used for style reasons but primarily functional purposes.

Sweat Band

Sweat Band

Exactly what you think it is. The sweatband can be made out of multiple different materials depending on the style of hat you’re wearing. For example, a dad hat will most likely carry a sweat-absorbent material such as cotton. On the other hand, a quality men’s wide brim will have a leather sweat repellent material.



The flange is right there with the brim and crown when it comes to defining the style of the hat. This part of the anatomy defines the overall shape and flow from the front of the brim to the back. The flange also denotes the side-to-side portion of the hat and this can define the lid itself. For example, a cowboy hat will have a very pronounced upward sweeping flange profile.

Obama Dad Hat

13 Types of Men’s Hats for Any Occasion
Now you understand the ins-and-outs of the game you’re ready to select your hat. The hat game is a tough one to get into, but once you’re in, you won’t truly feel dressed without one. The beauty of hats is there is one for every occasion. There are hats for the beach, for formal occasions, for cycling, and for keeping your head warm. Choosing the right one might be a challenge, we suggest you read our list on the 13 Types of Men’s Hats for Any Occasion and choose a couple.

stylish panama hat

  1. Panama
    Typically light in both weight and colour, a stylish Panama hat is your best warm-weather friend and a beacon of fun-loving vibes. Originally hailing from Ecuador, Panama’s are often made using the plaited leaves of a toquilla palm plant (which is technically not a palm but close enough to it). As a result, the hat is sturdy in construction and highly breathable. How to wear Panama? Being a summer and spring-time accessory, the Panama hat blends nicely with seasonal wear like crisp linen from the likes of Uniqlo or Polo Ralph Lauren.

Crown: High
Brim: Short/ Medium
Material: Panama hats are often made using the plaited leaves of a toquilla palm plant.
Dress code: Casual
Features: Typically bound with a coloured cloth accent.

Prada Bucket Hat

  1. Bucket
    The bucket hat is has made its triumphant return. This is one of the best hats for men who look to take their casual attire up a level. The bucket hat is exactly what its name suggests, a bucket in the form of a hat. This stylish accessory can be dressed up or down. This usually depends on the brand of bucket you wish to flaunt. A bucket with designer branding is a strong statement for the fashion conscience as much as a VB or XXXX bucket hat is for the footy fan. The sloping downward motion of the brim lends itself to those with paler skin tones and the heavy-duty construction means you won’t have to worry about it at music festivals.

Crown: Single round panel
Brim: Short
Material: Nylon/ Cotton
Dress code: Casual
Features: Provides 360-degree sun protection, branded version are a good fashion accessory.

pork pie hat

  1. Pork Pie
    A deserving addition to the list of cool hats for men has to be the pork pie hat. Worn by the likes of Buster Keaton and Walter White (aka Heisenberg), the Pork pie hat derived its name by loosely resembling British pork pie. As a close cousin to the fedora, these small and round men’s hats host flat crowns, creases along the inside top edge, and brims that curl slightly upward. When it comes to pork pie hats and suit combos, it usually finds its place within the smart casual dress code. Picture a navy blue blazer, a button-down shirt, khaki pants, a pocket square and a felt pork pie hat and you’re heading in the right direction.

Crown: Medium/ High
Brim: Short and slightly curved
Material: Wool/ Felt
Dress code: Casual/ Semi-formal
Features: Looks like an English meat pie.

Boonie Hat

  1. Boonie
    The Boonie hat (or booney) is a version of the traditional slouch hat. These lids originated from military use, particularly those who served in hot tropical and desert environments. The Boonie and bucket are similar in construction, however, this hat has a few extra tricks up its sleeves. This one is for men that have completely run out of space. With the Boonie hat, you can store anything that hangs from the comfort of your own melon. This is thanks to the Boonie hats webbing that surrounds the crown area and sometimes extended to the brim itself.

Crown: Single panel/ webbing sometimes attached for added function
Brim: Short
Material: Cotton and wind-resistant poplin
Dress code: Casual
Features: The Aussie version of the Boonie is sometimes referred to as the ‘Giggle Hat’.

trilby hat

  1. Trilby
    Sporting a low angle brim and pure retro vibe, the trilby occupies its own tiny corner in the men’s hat arena. Arguably, the most stylish hat for men, you might recognise it as the hat Inspector Clouseau wore in the Pink Panther films, as well as multiple appearances atop the crown of Mr. Bruno Mars. And although you might think trying to pull of the trilby is venturing into dangerous territory, the trilby has become one of the coolest hats for men and one of the more socially acceptable pieces of headwear. When you find a trilby with the right shape, fit and proportions, it looks pretty damn fine.

Crown: Medium/ High
Brim: Short/ Medium
Material: Tweed/ Rabbit hair felt
Dress code: Casual/ Semi Formal
Features: Looks like an English meat pie.
Features: A short brim angled down in front and turned slightly back

Baseball Hat

  1. Baseball
    Ahh the old faithful baseball cap. This is one of the best caps for men and has stood the test of time thanks to its ability to be worn with just about anything. The softly rounded crown and stiff front won’t conform to your head as comfortably as the dad cap but for some styles, that is exactly what we ask for. The baseball cap is typically worn as part of the uniform for major and minor league baseball players. Traditionally the front panel houses the team’s logo.

Crown: 6 panel
Brim: Front-facing medium length
Material: Traditionally made with wool, more recently, polyester.
Dress code: Casual
Features: Worn by major and minor league baseball players.

derby hat

  1. Derby
    Like the trilby, men’s derby hats (or bowler hats) are definitely an acquired taste. Commonly made of hard felt, this men’s formal hat features a short brim and rounded crown. Historically, these men’s dress hats have been associated with blue-collar and bourgeois alike. Nowadays, the derby is often viewed as a somewhat humorous accessory emanating with antiquated charm. Should you wear one, you’ll want to be supremely confident with how to wear a hat. Pair it with a classic three-piece suit and maybe a cane and you’ll certainly draw some eyeballs. Just be sure to tip it kindly when any high society Victorian women pass by. A guide of hats to wear with suits could never dare omit the derby hat.
Musician, Country Song, Banjo, Guitar

Crown: Medium
Brim: Short/ rolled
Material: Woolen felt
Dress code: Formal
Features: Hard felt, short brim, rounded crown

  1. Dad
    A must-have for many hat wearers, the dad hat has shot up in popularity thanks to its relaxed fit. Technically speaking, the dad hat might have copied all its homework from the baseball cap, but what it missed out on is what makes it special. The dad cap has an ever so slightly shorter brim, and the fit itself is more relaxed thanks to the use of softer materials. The dad hat has a longer pull cord at the back and the logo on the front is usually worn as an act of irony. Forget flat brims and snapbacks, the dad hat is where it’s at now.

Crown: 6 panel
Brim: Short/ medium
Material: Canvas/ cotton
Dress code: Casual
Features: The dad hat has a shorter brim than the standard baseball cap and a more relaxed fit.

fedora hat

  1. Fedora
    A fedora with a suit was once a mainstay of the business world. However, the fedora hat has broadened in appeal over the course of its long tenure. To spot these occasionally popular men’s dress hats, look for the indented crown with a lengthwise crease pinched near the front on both sides, along with a soft brim of about 2.5 inches or more. An appealing aspect of the Fedora is its versatility as a men’s fashion hat. Although, if you’re pairing it with a smart casual outfit, a kung fu grip on personal style is pretty much mandatory. If your reflection in the mirror is reminiscent of an early 2000s Justin Timberlake, then it’s best to remove it.

Crown: Medium/ High
Brim: Short/ Medium
Material: Felt
Dress code: Casual/ Semi formal
Features: Fedora hats and suits used to come in one package.

Straw Hat

  1. Straw
    There’s not much to say about the straw hat that hasn’t already been said. Straw hats come in a multitude of different sizes and style variations. This can range from the Bunnings straw hat you see in the crowd at your local cricket game, all the way to Fedora style straw hats that you see on the paddock at Flemington. Straw hats are synonymous as extra-wide brim hats for men and women that can be worn as a stylish statement and a sun-protecting piece of armour.

Crown: Medium
Brim: Wide/Very wide
Material: Straw
Dress code: Casual
Features: The straw hat is one of the cheapest hats for extreme levels of sun protection.

Nike Visor

  1. Visor
    There was a time when the visor was forced into retirement at the local tennis court. Today, visors are making a return to the mainstream thanks to an uptick in trendy athleisure and activewear. The visor is all function and very little style. If you’re feeling a bit overheated during your workout, grab a visor and find out why this men’s hat is the perfect hat for working out.

Crown: Non-existent
Brim: Short/ Medium
Material: Canvas/ cotton/ plastic
Dress code: Casual
Features: The visor is making a comeback. Once left for the tennis court, it’s now welcome for style.

flat cap

  1. Flat Cap
    Similar to a newsboy hat, the flat cap hosts a rounded top and a small, hard brim up front. These men’s hats are typically made of tweed, though other fabric variations do exist. In spite of the flat cap’s history among working-class types, it’s recently emerged as dressy weekend wear for younger men. Pair it with a tweed jacket, a handsome sweater or maybe a nice blazer with khakis, and go have a nice picnic in the countryside. Or you can just do brunch–whatever works for you. If a man is to ever wear a suit with a cap, the flat cap should be his first preference.

Crown: Classic 6 or 8-quarter panel crown
Brim: Short
Material: Wool/ tweed/ linen
Dress code: Casual/ Semi-formal/ Formal
Features: Rounded front brim

newsboy hat

  1. Newsboy
    Wildly popular at the turn of the 20th century, the newsboy hat is embraced by both male and female tastemakers. The newsboy hat is defined by a curved brim, eight panels and a top button. Thanks to the use of materials like wool, the hat makes for functional and fashionable cold-weather wear. There’s no need to go too fancy with this one–pair it with a smart casual or straight casual outfit and you’re ready to rock. If it’s cool enough for David Beckham, it’s certainly good enough for you. Just don’t overdo it on size.