A Man's Guide to Wearing Hats

This is a guest post written by Style Crew ambassador, Eric Rodriguez

When we think of hats, many of us, especially those in my age bracket, think of Cary Grant and Indiana Jones in their famous fedoras, Michael Corleone from “The Godfather” in his stylish Homburg and, most recently, Thomas Shelby from “Peaky Blinders” in his newsboy cap. Hats were very commonplace in the late 19th Century to the end of the 1920s. But sadly, nowadays hats are rarely seen (with the exception of a baseball cap).

That being said, of all the accessories a man can wear, a hat is by far the most stylish. A hat adds a touch of mystery, class, and sophistication to any outfit. It’s also a very suave way to finish off an outfit. Here are my three favorite hat styles and how I wear them.

Fedora & Trilby

The word fedora comes from an 1882 play where the heroine wore a center creased, soft brimmed hat. After Prince Edward started wearing them in 1924, it became popular for its stylishness and its ability to protect the wearer’s head from the wind and weather. In 1920, it was associated with Prohibition and gangsters. In the 1940s and 1950s, noir films popularized it even more. It wasn’t until the late 1950s when informal attire became widespread that the fedora became less commonplace.

The fedora, with its lengthwise crease down the crown and its ‘pinch’ on either side of the front, comes in various felt fabrics such as beaver, rabbit, wool, and straw (aka Panama, which is worn primarily in warmer climates). It also comes in various crown and brim sizes. It can be worn with the brim down for a classic, traditional look or the brim up for a more modern, youthful look. The classic look works best with more formal attire such as a suit or sports jacket. The more modern, turned-up brim, works well with jeans, khakis, and boots. Personally, I think it gives off that rock and roll vibe. In warmer weather, a Panama hat is the best option. It works great with a summer suit or linen pants and a polo shirt. My favorite fedoras are the Stratoliner and Whippet.

Like the fedora, the trilby also has its roots in the theater. The hat was first popularized in a stage adaptation of George du Maurier’s novel “Trilby”. It was initially worn as a “rich man's” hat in the early part of the 20th century and mostly only in Britain. The hat all but disappeared and didn't resurface until the late 70s as part of the retro scene and then disappeared again. The trilby is best known as the hat of choice by “Old Blue Eyes” Frank Sinatra. The trilby, sometimes referred to as a “stingy brim”, is similar to the fedora, but it has a smaller crown and brim.

Cowboy/Western Hat

If there’s one hat that is considered the most recognizable throughout the world it’s the cowboy hat. Recognized for its high crown and wide brim it is the defining piece of the North American cowboy. The first cowboy hat was designed by John B. Stetson in 1865 and was made popular by movie icons like John Wayne and Clint Eastwood. Nowadays everyone from cowpunchers to rock stars wears a cowboy hat. Unlike other hat styles, a cowboy hat takes a bit more confidence to wear especially if you live in a place like New York City where cowboys aren’t as common. One of my favorite—and most complimented—cowboy hat to wear is the classic Open Road. With its three indentations in its high crown, it gives an air of class and business.

Newsboy Hat/Flat Cap

The newsboy cap gets its name from its wide popularity with newsboys or “newsies”. Although it’s thought of as a boy’s cap, it was popular with men of all ages during the late 19th and early 20th centuries. Extremely popular with the working class, it wasn't limited to them. The upper class often wore them to more leisure activities such as golf or driving. The newsboy cap, also referred to as a Gatsby, paperboy, or applejack (as the wider, more floppy version is known as) is typically a 6 or 8 paneled cap with a front peak often made of wool or leather and lighter materials such as linen or cotton for warmer weather. The flat cap, sometimes known as a scally, is a rounded cap with a small stiff brim. Although these two styles of caps are often confused, the main distinction is that the newsboy cap is baggier and floppier than the flat cap.

Purchasing a Hat

If you’re purchasing your first hat it’s always best to skip the mall and department store and go to a quality hatmaker/dealer. These are the people who really know hats and can explain the difference between a quality $200 beaver felt fur fedora and a $20 wool-blend fedora. My first hat was a beaver felt Homburg which cost me $250. I instantly fell in love with the hat but wasn’t sure about the price. Once I was able to see and feel the differences between a quality hat and a cheap hat I was able to understand the reason for the price tag. Now I’m not suggesting that your first hat should cost you $200, but it’s always best to know and see the differences. A quality fur felt hat will retain its shape and color over time. Specialists, like Stetson, Borsalino and Akubra for example, focus on quality and design and not on trends.

Choosing a Style and Color

When choosing a hat style think of what your personal style is and what you want the hat to say. Since a fedora or cowboy hat is not something everyone is wearing it will get attention. For example, walk down the street in an Open Road hat and you will be noticed. A newsboy or flat cap is probably the easiest choice to ease yourself into wearing a hat. Its casual and unassuming style is easy to pull off and not as “attention-grabbing” as a fedora or cowboy hat. Color and texture are just as important. A neutral color like tan, brown or grey is the easiest to style with your outfits. Unless you’re looking for that “stand out piece, I’d avoid colors like red, yellow and multi-colors as well as large patterns.

So if you’re looking for something to add to your wardrobe that will make you stand out from the rest, give a hat a try.

Eric Rodriguez is a content creator based out of Brooklyn, NY focused on men’s style. He enjoys food, watches and fashion and is an up-and-coming model, having been featured in several campaigns for various brands. Currently, he is an ambassador for Ash & Erie as well as Beckett Simonon, the shoe company.

Check out his page here: @ericrnycstyle