The Hat

A Quick Guide To Men’s Hats

The men’s hat, once a purely optional accessory that was oftentimes seen as unnecessary in the latter portion of the twentieth century, is slowly but steadily making a comeback in the earliest part of the twenty first century. Though it’s not quite like it was in the 1950s when men rarely left their homes without a hat, hats are becoming more popular among well dressed men. There are a range of hats currently in fashion, the most prevalent of which are listed below.

Baseball Hat

The standard sportsman’s fare is a poor choice for formal occasions, but in more casual, relaxed occasions, a baseball cap is a fine choice for any man looking to wear a hat. Sporting events are where these are worn most commonly. However, a typical baseball cap is less than perfect for a man wishing to appear more mature and level headed. A worn in cotton baseball cap without insignia is growing more popular.

Chris Pine wearing New York Yankees Baseball hat


Widely associated with the gangsters and detectives of the earliest motion pictures, the fedora eventually became a near ubiquitous item in the wardrobes of many men before suffering a decline. Unlike baseball caps, fedoras are intended for more professional occasions and as such should ideally be custom fitted to each wearer. One should also be weary of combining a professional fedora with a casual outfit as this generally a recipe for disaster, particularly when one does not have a very fashionable casual wardrobe.

Donald Draper wearing a brown suit with a brown fedora hat


A beanie is a far more casual hat than the fedora and about on the level of the baseball cap. These hats are oftentimes worn during the coldest winter months in the parts of the world where cold is a serious factor in one’s fashion decisions. A number of fashion houses do manufacture beanies of varying styles and sizes. However, one should get a properly sized beanie, as a beanie that is too small will have an unfortunate tendency to slip off one’s head.

Hand-crafted blue beanie hat


The cabbie hat, also known as the taxi driver hat, is another more casual hat that can also bleed into one’s professional life if one is careful. Like the fedora, it is associated with days long past and those with a taste for the old fashioned may find a cabbie hat more to their liking then a fedora. It ultimately does come down to personal choice.

Male wearing black cabbie hat and grey scarf


This more formal hat is none the less likewise associated with the bootleggers and private investigators of the earliest movies and is a solid if somewhat less formal alternative to the fedora. Most people associate the bowler with the stuffier British culture, but others consider it less formal than the fedora or its cousin the homburg. Consider the occasion before choosing the hat.

1960's male wearing a suit and tie with a bowler hat.

Cowboy Hat

The cowboy hat is always a controversial hat, which is a bit unusual considering there are a wide range of hats that could be considered cowboy hats. While many regions of the American southwest consider the cowboy hat perfectly formal, most other regions of the world consider it either a curious eccentricity (and not always in a good way) or a costume accessory.

Man wearing a tan cowboy hat, white t-shirt and blue jean jacket holding a gun over his shoulders