When it comes to most occasions, a hat can be the perfect accessory. Who knew that there were so many different types, and not all are suitable for specific events or venues? From men’s winter dress hats to casual ones, we bring you a selection of styles. Continue reading for our guide to seven men’s hats and how to wear them well.

Seven Men's Hats and How to Wear Them Well - men, hat, fashion

1.Pork Pie

First donned by women in the 19th century, the pork pie became a staple in men’s wardrobes in the 1920s. This surge in popularity was due to Buster Keaton creating a signature look with one. In the mid 20th century, the pork pie hat became associated with African American music, such as jazz. In the present day, many fashionable men opt to wear this. It is the perfect accessory to wear alongside a stylish, clean suit.


This narrow-brimmed hat was once renowned for being a rich man’s hat, popular at horse racing events. The trilby hat became more commonly worn in the ’60s when American cars began to allow less headroom and previous favorites were too large. Nowadays, trilbies are made from various materials, making them suitable for all budgets and occasions. You can pair them with a smart suit or with more casual attire, such as a blazer and jeans combo.


The fedora is a hat with a soft, wide brim and an indented crown. Another which was initially far more popular with women, it became the ideal accessory for men during the 20th century after Edward, the Prince of Wales, was spotted donning one. Originally available in black, gray and brown, the fedora can now be found in a wealth of colors, meaning that you will be able to match one to your outfit.


Created by London felt hat makers, Thomas and William Bowler, the bowler hat was said to have originally been designed in order to protect gamekeepers from low hanging branches while riding their horse, the bowler hat is a close-fitting style. This hat was hugely popular with the working class in the United Kingdom, Ireland and the United States during the second half of the 19th century. It later became an essential accessory for the middle and upper classes. The bowler hat is a symbol associated with many businessmen in the 20th century, particularly those working in the financial areas of London. Also associated with silent movie actor, Charlie Chaplin, it became a bit of a joke for a while. However, it is now firmly planted as a fashion statement, with many men choosing to wear one alongside a dapper suit.

5.Top Hat

Certainly the most eccentric of all the hats in our overview, the top hat makes a powerful statement. Traditionally worn in formal circles alongside a morning suit in Western culture, it was widely worn until the 1960s when its popularity waned somewhat. The top hat was mainly associated with the upper classes. In fact, it is still an item that many men choose to wear when attending larger horse racing gatherings, such as the Royal Ascot in England. However, these days, the top hat has evolved somewhat, and it is anyone’s fashion accessory. Whether you are attending a festival or a wedding, donning a top hat can make you stand out from the crowd. In fact, you may even be seen as a trend setter. For an even bigger entrance, choose a bright color which complements your outfit.


The first of our two more casual offerings, the beanie hat was once associated with scruffy, grungey teenagers for ease of wear rather than a fashion accessory. However, it has evolved and can now work well for most ages. You could opt for a brightly colored version with a monochrome outfit to add a bit of interest. Alternatively, opt for a camel or gray to wear with a patterned get-up. Of course, it wouldn’t be suitable for wearing to a wedding, and most people would remove them when entering a building, but they can be a perfect accessory for winter dates and strolls in the park.

7.Baseball Cap

Our second and final casual suggestion, the baseball cap has been around for years and shows no signs of lessening in popularity. Forwards, backwards or off to the side, there is no right or wrong way to wear one. However, avoid wearing a red one backwards unless you are hoping to replicate Fred Durst’s signature look from the early 2000s. Still an informal hat, a baseball cap can be worn whether you are heading to the gym or for a dog walk, to visit the beach or while you spectate at a baseball game (its namesake!).