Q. You wrote recently about not overdoing cowboy boots and other regional styles, and I was wondering about hats. Are there hats that are accepted everywhere in the country, others that are local, and some that are completely out of style?  I have a mix of fedoras, cowboy hats with and without bands, and some Kangol, bowler, and other styles and don’t want to wear the wrong items when travelling.

A. Hats are an enduring, go-to accessory that are dear to the hearts of stylish men. Choosing a style depends on several factors including the occasion, the season, and what else you are wearing. 

Hats allow a man to make a fashion statement without being flashy or flamboyant. From baseball caps to fedoras, from bucket hats to cowboy hats, they are a versatile, functional, and stylish addition to any man’s look. Practical and suitable for any season, rain or shine, a hat will keep you warm (or cool), dry, and protected from the sun, all while looking great. A hat can finish off any dressy or casual combination with a bit of a flourish. Of course, you do not want to be wearing a winter wool hat on a sunny summer day, nor do you want to be sporting a baseball cap to a cocktail party, but there are other less obvious choices that are wrong (and right). 

Here are a few men’s hat styles you might see today and when and where to wear them.

Fedora

The fedora has stood the test of time. The most versatile of men’s hat styles, it continues to be popular in both the fashion and non-fashion worlds, and remains a great addition to a man’s wardrobe. The rather formal fedora has a “snap brim,” that can be worn either up or down to create a different look. It is seasonally available in wool felt or straw. There is no end to the looks you can create. Although the fedora comes in different colors, it is best to stay with those in neutral shades and medium width brims.  While you would not wear a fedora (or, I hope, any non-religious head-covering) indoors, there is scarcely an occasion when it is wrong outdoors.

Trilby

Despite often being confused with a fedora, a trilby is a slightly different type of hat. Also made in either wool felt or straw, it features a smaller brim and taller crown than the fedora, and has a more everyman look than the more stylish fedora. It is a shade less formal and, therefore, better suited to the man who likes to look good, but is not comfortable with anything that suggests he is overly interested in “fashion.” The brim is fixed, and cannot be snapped up or down. You would not generally wear a Trilby with a very dressy suit or, beyond that, with black tie. 

Bucket Hat

A casual cotton hat that keeps the wearer warm and comfortable, it does not go well with high-style clothes or fashion-forward looks. 

Cowboy Hat

The cowboy hat is an accessory with vintage-inspired style, but that is still modern. Certainly, it is a wardrobe basic in the Southwest, but I cannot think of anywhere in the U.S. where it would raise eyebrows, as long as the occasion is not too formal. So, do wear it at family gatherings, but not at important company meetings. 

Baseball Cap  

Today, the baseball cap is as much a fashion item as it is a piece of sportswear. Its simple design is an essential part of street style, making it immensely popular. Unfortunately, many men think of it as a go-everywhere item, when it really should be worn more selectively. And though it works for many casual situations, it is not an appropriate style for everyone. There is also a significant difference between wearing a ragged old team cap with dress clothes vs. wearing a company cap when visiting the warehouse or worksite; and a vintage cap might be perfect at a picnic, but be taken as an argument opener when visiting the towns of competing teams.

Straw Hats

Straw hats are summer essentials most suitable for warm weather and tropical destinations. They range from the popular fedora-shaped Panama hat (which actually hails from Ecuador) to old-fashioned flat skimmer hats (also known as boaters). Though the flat straw skimmer with a colorful silk ribbon around its crown, was a nice alternative to the Panama, it is much too dated and seldom seen today. It would look like you were in a costume. Many straw hats are breathable, foldable, and packable. They are great for summertime travels. 

Newsboy Cap

Similar to flat caps, newsboys consist of a stiff peak and a round body. They are usually lightweight wool. Worn by fashion-conscious men for hundreds of years, they’ve long remained popular, but are not for everyone. If you’re visiting people and locations where others might be surprised by the choice, you should consider to what extent you want to stand out.

Hat types that are out of style and seldom, if ever, seen these days include: bowlers, derbies, pork pies, top hats, berets, and skimmers.

Time was when all men wore hats. We can all remember seeing old photographs of a sea of men wearing hats at something as casual as a baseball game. Men’s hats will never entirely come back to the level of popularity that they once had, but, for those who enjoy clothes and setting themselves apart from the crowd, they are a great choice.

The two most intriguing quotes I have heard about men’s hats are quite telling: “The function of a hat is threefold: to shock, mystify, and delight any and all observers.” And “Historically, men wore hats to fit in; today, men wear hats to stand out.”

Please send your men’s dress and grooming questions and comments to: MALE CALL: Lois.Fenton@prodigy.net