Just like before when we talked about dress shoes and knowing a little bit more about what you are wearing I thought this would be another good and informative read. As sartorial menswear continue to rise, we see how certain classic items being revived and made to look cool and complement a modern gentleman’s look. These classic hats have revolutionized men’s wardrobes and continues to reign. I can testify and say I have worn hats and didn’t know what style hat it was. I remember back in the days growing up, people used to call any classic hat a “DOBBS” and I also continued calling them that. It was until I went into a store in town which stocked American and English brands and I saw different hat styles, surprisingly all those hats were branded with the name “DOBBS”. It was then when it clicked that “DOBBS” was a brand and not a type/style of a hat. As much as we know by now that style is personal and often differs from gentleman to gentleman, below we look at classic hats that men should at least know and perhaps own one or two.



This is arguably one of the iconic of all classic hats, many regard this one as the gangster’s hat. The likes of Al Capone, (famous American mobster) wore a Fedora and even the gangs of Kofifi Era in Sophiatown embraced it. It is traditionally made of felt material and has a flat and flexible brim that one can bend upwards or down on either side depending on the wearer’s style. It has a lengthwise crease down the crown and has two dents on both sides in the front.



The classier version of the Fedora, the Homburg is or rather was mostly worn by business men and politicians back then. It’s either made of felt or straw but the brim is slightly stiffer than the Fedora and its always turned upwards all the way round.



The shorter (smaller) version of the Fedora, because of its shorter brim. The front of the brim is slightly tilted down and the back is turned upward. It also has the two dents on each side in front and creased on the crown. Some hats such as this one here are not necessarily for the sun shade but just to complete and compliment a gentleman’s ensemble.



This particular hat is familiar with hipsters and jazz musicians. Like the Homburg, it also has a rolled up brim all around the hat. It has a flat circular crown with no crease but has the two dents on both sides in front just to have that triangular shape.



Although both the names mean the same thing, this hat is well known as the Bowler and it is one of Britain’s iconic hats. Some may recognize this hat from the famous English comic film actor, Sir Charles Spencer “Charlie” Chaplin who rose to fame during the era of silent film. Just like the Porkpie, also has a rolled up brim all round. Its distinct look is captured by the round, dome-looking crown with no crease nor dents.



Another classy hat for formal and prestige “suit-&-tie” occasions. The Boater is also made of straw but the whole hat has a stiffer-to-hard feel. Both the crown and the brim are flat and can’t be bent nor pinched, but the most attractive part of this particular hat is the colourful or striped bond or ribbon. A boater is a summer hat that was worn back then for sailing or boating, that’s why is called the Boater. 




 Another summer hat, but for casual relaxed occasions. Confusingly so, it originates from Ecuador but then were made and shipped to Panama for the workers at the Panama Canal. It is woven out of leaves of a palm-like plant and it is one hat that can be squashed and twisted and would still retain its shape.



This is the recently popular and trendier hat for the modern gentleman. I can call this the modern Fedora because of its creased lengthwise crown and the two dents on both sides in front. The only distinct difference with this particular one is the (wide) brim, exactly how the name came about. These modern style hats differ with brims, some are stiff and cannot be tilted and some can be tilted right round.


Also known as the “newsboy” it’s another legendary head gear world-wide. It was also common in North America and the European countries, worn by boys and all the working class men in the 20th centuries. Most commonly these tweed woven hats were popular on the golf course in the then era of the likes of Walter Hagen and Ben Hogan.


Some would agree that hats are becoming like sun glasses worn by celebrities, come rain or darkness the shades are always on. We’ve seen these hats being worn through-out the year and substituting each other through seasons and wardrobe change. We can all agree that hats are not just for the shade from the sun but a classic and timeless accessory to keep us looking as stylish as ever. However as gentlemen, we may gladly wear our hats in the dark but let’s not do so in the house unless it’s a public space.*wink*


Until next time, stay stylish…

Suitably Yours

Brian Lehang




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  1. Now I know classic hats that I didn’t know before…Thanks for the info my brother….

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