Style Statement: Hats

For the stylish man, we sometimes revisit the trends and customs of old in order to reaffirm and reinvent who we are today. One of the most fascinating and distinctive accessories in men’s style, which has boldly reintroduced itself into the world of men’s couture: The Hat! The right hat, paired with the right outfit is what we aim to achieve. When a man is building his individual style, he must be careful not to complicate things by trying too hard. When we try too hard, it often comes across that way. Since style is about individuality, we must find the simplest way of expressing who we are in the pieces we couple together.



In the world of fashion etiquette, there has been a circulating argument about whether the hat is to be categorized as an article of clothing or an accessory. Until the 1960s, most men would not leave their homes without wearing a hat. During that time, wearing a hat was just as imperative as wearing a shirt or pants. The hat symbolized dignity and a man’s respect for others as well as himself. With the shift from men’s formal wear to more casual wear, the hat began to lose its significance in menswear and became more of an accessory than a necessity. The same holds true today. One should not depend on the hat alone when putting together an outfit. Rather, think out the details of the entire ensemble with the hat as the complimentary piece.


Be it the Fedora, Top Hat, Bowler, Trilby, Homburg, Pork Pie, Ascot, Panama, Beret or the Beanie, hats make for an amazing addition to any wardrobe and offer a certain pizzazz to the overall look. My personal favorite is the Bowler hat aka the “Coke” or the “Derby” (the term more commonly used in the US). This hat is typically snug fitting to prevent it from easily falling off the head. It is made of sturdy felt, a narrow brim and a rounded crown. It was designed to protect riders from low hanging tree branches. Fast forward into the 21st century, we seldom see men wear hats such as the Bowler apart from the Royal Family while on their official duties, or perhaps the more daring modern-classic man who would like to spice up his outfit for a night out on the town.

The Fedora Look


Classic hats when coupled with a suit can enhance the man’s style as well as gain him the respect of other serious-minded people.  There are many exceptions to the rules of hat wearing and accessorizing. Below are a few practical pointers to assist you on your new journey:

  1. First, take time to try on various hats, particularly the more unconventional ones. Try hats on while wearing one of your favorite outfits. I would also recommend that you take photos with these hats mentioned in this article to see which one would be your staple look.
  2. Since the hat frames your face, the general rule is to choose a color that would complement the shape and complexion of your face and/or hair color. Generally the darker you are, the brighter the color you can accessorize with. This is one that you have to play with to see what works best for you.
  3. In order for the hat to fit properly, it is important to get an accurate measurement of your head size prior to choosing the hat. Use a measuring tape by circling it around your head just slightly above your ears and eyebrows for the proper measurements. It is advised to measure several times and notate your results to find the most accurate size. As a rule of thumb, any hat-measuring chart that includes both U.S. and European sizes is ideal to reference.
  4. To the youth, I would suggest to not shy away from wearing a more mature, classic hat simply because of your age. When done right, a younger man wearing a classic hat tends to come across as more appealing and distinguished than it would on an older gentleman.
  5. When determining whether or not to wear a specific hat for a specific occasion, remember that you are the one wearing the hat and not the hat wearing you. Again, the hat is an accessory which should only compliment the rest of your ensemble. The idea is for the whole outfit to be commended including the hat as the topper.
  6. Lastly, have fun with this journey. These are simply tips to guide you subject to your individual preference and interpretation.

If you are in New York City, for a dapper hat experience, stop by the famed Flamekeepers Hat Club.

Brian Hampton

Brian Hampton, the Founder of Dress Like a Gent an online journal created to help gents develop their own personal style. Brian is a bilingual professional in French and English, style instructor, men's style blogger, as well as a minister. He is currently based out of Atlanta, Georgia.​ Instagram: DressLikeAGent Twitter: _DressLikeAGent


  • Reply April 30, 2015

    Sheila Anderson

    What an articulate and very exciting article about a HAT!! This short history lesson brought much needed awareness to helping young men and old add the cherry on top of a proverbial sundae. Mr. Hampton’s passion and knowledge of every aspect of current haberdashery makes him my “go-to GURU”, hands down.

    Hats off to you, Sir Hampton!

  • Reply May 1, 2015

    Rev. Michael Clinkscales

    Excellent article and very informative!

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