A Modern Guide to Men’s Hat Styles by American Hat Makers


A Modern Guide to Men’s Hat Styles

How and When to Wear These Classic Men’s Hat Styles

There’s something iconic and illustrious about a man in a hat, yet knowing the what and when it’s appropriate to wear a particular style can be daunting. Not every occasion will feel like a prompt to showcase a fedora like Humphrey Bogart, nor will the silent act of walking into a speakeasy give everyone the urge to tilt their pork pie hat like Buster Keaton (if you don’t know who that is, picture Walter White from “Breaking Bad”). In fact, the centuries of social, cultural, and environmental influence that helped shape today’s full gamut of fashionable hats only add to the confusion since “trending dress codes” are always evolving. 

So how do everyday hat wearers know when it’s right to add a suave touch to their get up or cover the fact it’s been days, maybe even weeks, since they last washed their hair? How do they know what types of hats will protect their head against nature’s elements in a cooling or warming atmosphere, while also airing a tinge of fashion? They refer to our Modern Style Guide to learn what types of hats suit certain occasions so they can effortlessly add this versatile men’s accessory with confidence.  

Victorian and Steampunk Top Hats

As a symbol of urban respectability in the 19th century, there has never been a more sophisticated and dominating hat in fashion than the top hat. When first worn in 1797 by the man credited as its inventor, haberdasher John Hetherington, it was documented that “a passersby panicked at the sight, several women fainted, children screamed, dogs yelped, and an errand boy’s arm was broken when he was trampled by the mob.” With such a response it makes sense that The Penguin, The “Mad Hatter” and rock star Alice Cooper opted to sport modern day versions of the Victorian-inspired hat. 

Although the Victorian wide brimmed, tall crowned men’s top hat was historically made from felted beaver skin, today’s styles include brown, black, gold or even white leather and mesh. To add even more character and personality to the attention-grabbing accessory, a subcategory of Steampunk top hats was created. Steampunk top hats embody the truest essence of fantasy and creative exploration with their limitless usage of color, material, and hat band decor or trinkets. 

If you want to make the ultimate impression that causes an uproar of attention, then the Victorian or Steampunk top hats are the way to go. Festivals, special occasions, costume parties, and themed events may be the primary places to wear this style. However, if wearing it makes you feel like Robert Downey Jr. in the World of Superheroes, then everyday and every occasion is an opportunity to wear a top hat. 

Wide-Brimmed Fedoras

The fedora first hit the fashion scene in 1882 when the famous actress Sarah Bernhardt wore one in the play “Fédora.” In the 1920s, Prince Edward of Britain showed men that they too could style the iconic handmade hats. The fedora hat has since become associated with late night activity of gangsters, musicians, actors and models. It has an edgy yet sophisticated and elegant look, which is precisely why you’ll see Justine Timerlake, The Blues Brothers and Johnny Depp wearing them.  

If you’re looking for the ultimate gentleman’s style, then choose to wear the wide-brimmed fedora. The wool and felt versions are perfect for the fall and winter, whereby the straw fedoras offer a lighter more breathable option for the summer. All in all, the aesthetic is often paired with a collar and is perfect for any upscale occasion, business event, or event that requires you to make a favorable impression.

Trilby Fedoras

Just as all fashions evolve over time, the wide-brim fedora has been modified into a narrower brimmed version called the trilby. Worn in the first production of the novel Trilby in 1894, the hat regained popularity in the 60s, 80s, and once again the 21st century as a retro trend. 

The trilby has a compact but taller crown, which often highlights high-set shallow indents for a stylish, tear drop shape. The brim is curled on the edges and the hat is worn slightly farther back on the head so that it sits at an angle. It’s a great option for the carefree and fun individual looking to accessorize his pair of stylish jeans. Wear it throughout the day and seamlessly transition into a formal dinner downtown then a late night jazz club with class.

Cowboy or Western Hats

The first American Cowboy Hat was designed by John Batterson Stetson in 1865 and he called it the “Boss of the Plains.” The straight-sided crown with rounded corners provided insulation for the top of head, whereby the wide stiff brim provided shelter for the face, neck and shoulders from both the sun and precipitation. The durable, lightweight and waterproof option was made from the highest-quality materials. It quickly became regarded as an investment for the working cowboy, a statement of success for the city dweller, and the universal image of the American West. 

In this day and age, cowboy and western hats are no longer reserved for the rodeo bronc riders! Instead, the Stetson-inspired designs have been turned into a variety of styles that represent both the allure of the Wild West and the comfort of a ball cap. There are small brim cowboy hats that will make you feel like Billy the Kid, gambler hats that remind us all of Gone with Wind, and more traditional wool, felt, straw or leather cowboy hats that will complement your favorite pair of boots. 

There aren’t many stipulations as to when and where to sport your favorite western hat style, however there is an unspoken requirement to act like a gentleman with proper etiquette when doing so. Take your hat off at the table (some would say when you walk indoors), and always remove it during the National Anthem. 

Panama Hats

Despite their name, these hats originated in Ecuador and became popular during the historic Gold Rush when prospectors traveled from Panama to California. When admired by the masses, travelers told people they bought them in Panama, and the name stuck. From the 19th century to the 1950s, everyone wore Panama hats as a part of their wardrobe. Today the light-colored, lightweight hats are gaining just as much popularity. David Beckham, Mick Jagger and JFK have all worn this style with pride. 

Panama hats (also known as tequila straw hats) are similar to fedoras, however they have a central dent in the crown that’s pinched at the front and are made from a variety of straw weaves. Designed in a variety of shapes to match different face sizes, the Panama hat can be worn with just about anything. Embrace a sophisticated Riviera style or spruce up your outfit for your friend’s summer bbq, it doesn’t matter because these hats are meant to look great day or night.   

Outback Hats

The Australian Outback can be a harsh environment requiring durable yet hardy protection and rugged but supple gear for survival. With these specific needs, the outback hat was designed to ward off the weather and fold up into very small spaces while retaining its original shape. In 1874 the Keir family began manufacturing the original outback hats, called Akubra hats in New South Wales. “The Man from Snowy River” wore an Akubra in the well-known movie and has been an icon of mystery, romance, and western allure ever since. 

Similar to cowboy hats the felt, straw, canvas, and leather outback hats add a tinge of excitement and practicality to any get up. They represent adventure and are perfect for hiking, camping, travel, riding horses or anything that involves rooming the territories outside the city. Wear it for functionality and be seen as a rugged symbol of fun. Just be ready to say what Indiana Jones once said, “Jock! Start the Engine!” because you are sure to be on a ride. 

Pork Pie Hats

Pork pie hats, also called English pastry hats, first came about in Britain around the late 19th century, but became popular in the 1920s after silent film star Buster Keaton wore them in several of his movies. The classic small round hats with a narrow curled-up brim, slightly domed crown, and band fastened around the crease were more recently given attention after Walter White’s alter ego ‘Heisenberg’ wore one in Breaking Bad. To add to the limelight, fashion writer Glenn O'Brien of GQ magazine once said pork pie hats are, "the mark of the determined hipster, the kind of cat you might see hanging around a jazz club or pool hall... a Tom Waits, Johnny Thunders kind of hat." 

It is suggested that anyone with a long, short or oval shaped face will look good in pork pie hats. Their slightly squatty appearance and colorful bands make the hats a more casual option for sporting events or jazz clubs. The style suits events that emanate culture, such as horse-racing, golf, or art showings. 

The Ultimate Truth Behind This Guide

Whether the reasoning is ornamental or practical, men have been accessorizing with stylized head coverings since the Egyptians wore conical straw hats in 3200 BC. Since style will forever be evolving, and what was once deemed trendy and all the rage today may be seen as classic or even out-dated tomorrow, we want to mention one more important fact. 

The ultimate truth behind this guide is that every hat can suit every occasion, IF, and only IF,  the head under the material wears it with confidence and class. Yes, there are several styles that fit certain circumstances for practical and/or functional reasons. However, we believe that style refers to a person’s particular way of expressing themselves and we encourage everyone to do precisely that.