A Visual Guide to Men’s Dress Hats

The 10 caps that will instantly make a statement

Written by Meghan Salgado

When looking for some protection from the weather, one of the first things most of us reach for is a hat. Whether it’s a baseball cap for summer or a knitted beanie in the colder months, your casual staples may seem like enough. However, there’s a whole world of men’s accessories that have taken the back seat in recent decades.

Whether you have an affinity for vintage style or just want to stand out, adding a dress hat to your ensemble is a seamless way to make a statement. Not sure what’s out there? Check out our guide to learn more.

The Bowler

Thomas and William Bowler invented the bowler hat in London in the late 19th century. Also known as a derby hat in the United States, Charlie Chaplin made it famous.

Today the bowler hat will add an eccentric touch to your formal get-up. We recommend choosing a different hat if you have a rounder face, as this silhouette is more flattering when paired with an angular jaw.

The Flat Cap 

The Flat Cap is known by more names than we care to count — some of the most common alternatives being the ivy cap, cabbie cap, or driving cap. This style is categorized by a rounded cap that sits close to the head and the short, stiff brim. It’s usually made from cold-weather fabrics such as wool, tweed, and cotton.

This style is a step up from the baseball hat but can still be worn with your casual wardrobe.

We suggest you choose a fabric that’s different from your overcoat —matching isn’t always a good thing. For an updated look, go for the same shape in a suede or herringbone fabric. This little change goes a long way.

The Ascot

The ascot cap looks like a cousin to the flat cap. However, instead of being made from a soft material that sits closer to the head, the ascot is made from a hard round felt material.

This style looks good with both casual and more formal attire. If you’re wearing a suit in an unconventional fabric or like tweed or plaid, consider adding an ascot for a vintage touch.

The Fedora

The fedora is probably the best-known hat on this list, but not always for the right reasons.

A fedora is a brimmed hat with an indented crown. The biggest variations in this style come from the fabric its made from and the size of the brim.  A particularly polarizing style, the fedora is notoriously difficult to pull off.

For an updated look that’s more fashion-forward than dad on vacation, we recommend a felt or wool style. If you’re serious about looking good in one of these, go to a hatmaker and get sized.

Like with most articles of clothing, you can’t go wrong with quality materials and good fit.

The Boater

The boater hat is a summer style characterized by its straw weave and wide, round brim. It has Ivy-Leaguer connotations and is most recognizable as the style worn by barbershop quartets. Today they’re still worn at major boating or horse races. 

More recently its become more popular as a way to dress down a more formal look in the summer months. However tread lightly — with its wide brim, this hat certainly makes a bold statement.

The Trilby

This hat is similar in shape and make to the fedora, but is characterized by a narrower brim and shorter crown design. The 1960s style was popular as a driving hat when men were looking for something with a shallower top to deal with the shorter ceilings of American vehicles.

This style hasn’t seen much of a resurgence — most people favor the fedora.

However, if you have a smaller face, this hat could be right for you. It won’t overpower your features with its shorter brim. 

The Pork Pie

The pork pie hat has gone through several revamps to get to the style that’s worn today. Made of both straw and felt, this hat has a shorter round crown, narrow brim, and associations with the jazz and blues culture.

This hat is easy to pull off and worn year-round — opt for felt in the winter months and straw when it’s warmer out. This style doesn’t have to look dated if you pair it with updated classics.

The Panama

The Panama hat is a wide-brimmed, straw style. It’s sometimes worn with a ribbon around the crown and has roots in South America.

Try out this style in the summer months. They look great when they’re paired with light-colored or linen suits or other summer styles.

The Homburg

The homburg is a formal hat with a tall, indented crown and wide brim. Less recognizable than the top hat, the Homburg was worn throughout the 20th century but has seen a dip in popularity in recent years.

The larger proportions of the hat lends itself well to bold statement, but this isn’t a style you’ll see too often.

The Top Hat

If you’ve ever played Monopoly, you’re familiar with the top hat. This classic dress hat is categorized by its tall, flat crown and wide brim. You’ve probably seen it worn by historical figures from Abraham Lincoln to Winston Churchill.

This may be the dressiest of the hats listed here and today they are a touch too formal for most events. Unless you’re going to a royal wedding, we suggest leaving this style to the board game.

Top it Off

Rocking a dress hat may seem like a lofty style goal. But, if you do it with confidence, you’ll be getting those double-takes for the right reasons.

Ease into it with an easy-to-wear hat like the trilby or flat cap. Once you’re comfortable with those, the bolder styles won’t seem so daunting.

Photo of Meghan Salgado

Meghan Salgado

SOURCE: THE GENTLEMANUAL