Staple #24: The Hat

This is bound to be a polarizing post. There are few articles of clothing that lead to judgment and categorization as quickly as a hat. If I say “ten gallon” there’s an immediate image in your head. Same goes with “bowler”, “flat-brimmed snapback”, “fedora”, or “three corner.”

Up until JFK started changing the tide, a man would never be caught dead out in public without a hat. It protected him from the elements, shaded his face (before the advent of sunglasses), and was considered a modest aspect of polite society.

While a hat used to be commonplace, it’s now considered a statement piece. You don’t see hats on the majority of men with whom you interact daily, so a headpiece tends to draw attention and make the man wearing it both more memorable and more recognizable.

Even if you don’t wear a hat nine days out of ten, there are still the occasions that call for one. You may have jumped out of bed with no time to shower or comb your hair, it may be so cold that you need every layer of protection available to you, or you may be wanting an extra piece to add to your outfit as a way to avoid looking too average. Whatever your motivation, every man will find himself in need of a hat at some point.

There are as many hat choices as there are individual styles, so the purpose of this post is not intended as an expose on what’s good and bad amongst them. It’s just as possible for an old ball cap to look good as a fedora. Of course, both can just as easily look terrible.

For the sake of versatility, I do believe there is one hat type that rises above everything else – the flat cap.


Flat caps can be traced back to 14th century England. During the 19th century they were worn almost universally by working-class men and were also considered acceptable country attire for the upper classes.

They are characterized by their round shape and small, stiff brim up front.



While we may lament the death of tradition and formality in modern attire, trying to revive it by wearing items such as tailcoats, spats, and top hats comes across as overly affected and/or unrealistically nostalgic. Therefore, it’s much better to nod to tradition by adopting styles that were worn by the working-class or were considered part of the casual attire of the dreaded ilk of the aristocracy and¬†bourgeoisie.

Because of its origins, the flat cap is acceptable in every environment except the most formal.

By now you should know the way the rules apply to these hats(it’s the largely the same as all other Staple items):

Wool for the cooler months with linen and cotton for better seasons.

Larger patterns and bolder colors will make the cap appear more casual and darker colors with minimal or no patterns will be more formal.

Fit is still king, and – while it’s possible to wear a hat that’s so big it falls off your head or so small it won’t fit around your skull – the more common fit error is choosing something that’s just a bit too small. You don’t want a cap that gives you a headache after more than a couple of hours of wear.

As I said above, it’s more imperative you own a hat that is consistent with your style. So if a ball cap, military hat, or even a trilby is more up your alley, go with it.

However, if you want an option that will have the largest range of flexibility while not being too obviously attention-seeking, then a flat cap is the way to go.

Meet The Author

Tanner is the founder and primary author of Masculine Style. He lives in Salt Lake City, Utah with his wife and two kids, and helps run Beckett & Robb - a men's clothing company built around custom suits and shirts.


Jonathan Szeto

Also, since it’s been largely forgotten, some basic hat etiquette:
1) Hats are outerwear, so take them off when you go inside. Do you wear your overcoat inside the office?
2) Take off your hat as a sign of respect, when the occasion calls for it (e.g., playing the national anthem, when passing a funeral procession, etc.)

Peregrine John

Some will say, in absolute self-assuredness, that every man should always wear a hat. Others (with equal hubris) will declare that no man who is a man will ever wear a hat. I consider each to be entirely useless, not to mention stupid.

This article, on the other hand, is a lovely overview.

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