Men’s Dress Hat Styles Guide

Men's dress hat styleBellissimo Hats provides high-end hats for any style and any occasion. Whether you are out on the golf course with business associates or attending a party with friends, a well-made dress hat is a great way to stand out from the crowd. In fact, choosing the right men’s dress hat can ensure that you exude the kind of qualities that best reflect your personality and style.

Are you a person who likes to retain a sense of mystery and intrigue? Do you want to exude confidence and masculinity wherever you go? Or do you want to update your style by taking elements from both the past and present? No matter what you are looking for, Bellissimo Hats has something for you!

However, picking the perfect hat for your personality, style, and look is not an easy task. You will have to analyze yourself and your current style to see what — if anything — you would like to change about it. In any case, Bellissimo Hats offers a wide range of quality dress hats for men. So, let’s take a closer look at all of our hat styles to find the perfect fit for you!


The Fedora is a dress hat that has been around for years and will never go out of style. Though it is often associated with men’s dress wear of the 1930s, 40s, and 50s, it still retains the classic style and masculinity as it did nearly a century ago. Today, there are even more styles, colors, and varieties to choose from!

For example, the classic Panama hat is one of the most popular Fedoras in our collection. The Panama hat originated in Central America, though its exact story is something of a mystery. Some historians claim that this famous hat dates all the way back to the Incan Empire! Perhaps due to its longevity, the Panama hat is instantly recognizable the world over. Typically made from straw or similar material, Panama hats are the perfect accessory for a sunny day at the beach or a pleasant stroll through the park.

If you’re looking for a more classic Fedora look, we have plenty of options in a variety of styles and colors. You can get a wide brim Fedora that is both stylish and a great way to keep your head and face protected from the sun. Regardless of the brim size, you can also get your Fedora flat-brimmed or with a turn-down brim. Either style is great for both formal and informal settings. In short, there is a Fedora for just about any look or occasion you can imagine!


Though not as well known as the Fedora, the Trilby hat is another classic dress hat that dates back to the 19th century. Many people confuse the Trilby and Fedora hats because they have similar designs. Both hats feature prominent crowns, colored bands, and brims in a variety of shapes and sizes.

However, the Trilby is differentiated by its relatively stiff, stingy brim that is permanently turned down in the front and up in the back. While a Fedora is distinguished by a somewhat malleable brim, the trilby brim is fixed in place. This means that the brim will look the same on day one as it does three years after you buy it. Moreover, Fedora brims tend to be much wider and flatter by comparison. If you still need a frame of reference to tell them apart, Frank Sinatra was well-known for wearing the Trilby style, while the character of Indiana Jones is synonymous with the traditional Fedora!


The Homburg hat combines the old-school appeal of a dress hat with the modern style of the 21st-century man. In fact, the Homburg style reflects a mixture of many different styles, with elements from both the standard Fedora and the Derby hat of years past. If you’re unfamiliar with the Homburg, it might help to know that the style was made famous and popular by Winston Churchill. Today, the Homburg is a great choice for weddings, black-tie events, and photoshoots. While it may not be as common to see in casual settings, you can still pull it off with the right attire and swagger!

The Homburg can come in varied styles and colors, but it is most distinguishable by two distinct features: the crown and brim. The crown is noticeably more round than the Trilby or Fedora. Additionally, the brim is turned upward on all sides. This ensures that, with proper care, the Homburg hat can keep its shape and luster for years to come!

Pork Pie

In recent years, the Pork Pie hat became the signature style of Walter White (played by Bryan Cranston), the central protagonist and antihero of the popular television series, Breaking Bad. However, the hat has been around since the mid-19th century and has gained newfound popularity in recent years. Though it may not be as formal as the Fedora or Tribly, the Pork Pie hat is a great option for those who want to look stylish in any kind of setting.

Pork Pie hats have a flat-top crown and stingy, upturned brim. High-quality Pork Pie hats are generally made with a fur-felt material. Though colors can vary, the Pork Pie hat usually comes in darker shades, like grey or black. For this reason, you can easily pair the Pork Pie with formal attire (like a dark suit) or even informal attire. That said, most of our hats (including the Pork Pie) usually look best with a nice sports jacket!

Derby or Bowler

The Derby hat (also known as the Billycock or Bowler hat) became popular with the British and American working classes of the 19th century. Moving into the 20th and 21st centuries, the material and durability of the Derby hat lent itself to be worn in both formal and semiformal environments. Today, the men’s Derby hat is a great accompaniment to matching suits and tuxedos.

While the Homburg still retains some crown designs like that of the Fedora, the Derby hat has a completely rounded crown. This ensures a comfortable fit, regardless of your size specifications. The brim is stingy and turned upwards on all sides. Some designs also feature a flared brim that is raised on the sides and flat on the front and back.

Open Crown

If you’d like to explore your more adventurous side, the Open Crown hat is a great option. Based on the stylings of the traditional cowboy hat, the Open Crown felt hat takes the same principle design and adapts it to a dressier design. So, while the Open Crown may have a more “country” look, it is suitable for both formal and informal occasions.

The Open Crown hat typically has a round, tall crown that is decorated with a band of a matching color. The brim can vary in both length and style. Wide-brimmed hats are typically flat and provide greater protection from the sun, while smaller hats often feature a stingy, upturned brim. In either case, the Open Crown is a classic design that will not go out of style any time soon!

We hope you enjoyed our style guide on Men’s Dress Hats! If you’d like to acquire a high-quality dress hat for men, be sure to check out Bellissimo Hats today!