How to Wear Hats

Most stylish men secretly wish they’d been born in an era when hats were standard attire. If you’ve never donned a proper hat like a fedora or pork pie hat we can tell you that the feeling it bestows is similar to wearing a tuxedo or a military dress uniform. You simply feel more masculine.

Although the days when all men wore hats are not likely to return, it’s all the better for daring types who relish the opportunity to showcase a little individuality.

So, if you’ve ever been tempted to bust out a hat but are concerned that it might be too ostentatious, here are a few tips on how to put one on — and pull it off.

The easiest hat to wear (besides the baseball cap variety) is a tweed newsboy cap. Because they’re less formal, they’ve managed to remain more common and will not convey an overly retro vibe. Wool for fall and winter, linen or cotton for spring or summer, they’re super versatile and pair with a polo shirt or sweater just as well as with a jacket and tie.

For proper hats like panamas and fedoras, it helps to remember that every feature of men’s clothing was developed for a utilitarian purpose (like bellowed pockets on tweed hunting jackets, which made it easier to carry shotgun shells). So with hats, start by realizing that their primary function is to protect the head from the elements. Wearing a fedora in the wind, cold, and falling snowflakes will greatly reduce any self-consciousness you might feel, since your hat is actually serving its purpose. Ditto for donning a panama, which makes perfect sense if you’re in the sun all day.

Finally a word on hat etiquette. Tipping your brim at every passing lady would be anachronism overload. As for removing it indoors, this only applies to intimate environments like someone’s home, or a meeting in a private office. You don’t need to remove your hat in the lobby of a theater, though you probably should when you take your seat. The folks behind will thank you.


  1. thank you for explaining male hat etiquette

  2. You are very welcome, Lois! We are glad to hear that you found this post to be helpful!

  3. I love wearing hats,particularly in winter. The problem I have is getting them cleaned and blocked. That is an old tradition that few establishments offer.

  4. I really enjoy wearing my cowboy hat. Lots of compliments. Wish more hats were worn these days.

  5. Thank you for sharing your thoughts with us, Ben!

  6. I like standing out in a crowd and wearing my hats help me to do that especially the ones from Paul Frederick

  7. Thanks for sharing, Nathaniel! We are glad that we are able to help you stand out in the crowd!

  8. Thank you for your comment, Larry!

    One of the few places that still clean and reshape hats are Tack Shops and western stores. Keep in mind that reshaping is typically reserved for Fur Felt and stiffened wool hats. They are able to do this by heating the shellac in the hat until it is soft and reshaping by hand. Not all hats use shellac as stiffening and therefore are not all reshapable.

    Most of our felt hats are Lite Felt and are a lot more resilient than a traditional felt hat. The following are tips you can follow to care for your hat yourself:

    – Never put the brim of a hat on a flat surface. It can flatten the brim. Keep hat upside down on its crown. Store on a clean surface or in a hat box.
    – Try to avoid handling your hat by it’s crown to avoid soiling. You can pick up and adjust your hat using the brim.
    – Do not leave you hat in the car or extremely hot areas. The hat can start to loose shape and even shrink in the heat.
    – Remove surface dirt from a straw hat with a clean damp cloth. Lightly Spot clean.
    – Remove surface dirt from a fur felt hat, with a soft brush.

    I hope this information is helpful. If you have any other questions, please let us know!

  9. Hey now! I heard of your shop on Pandora. You’re right, men do want to wear hats but most of us don’t have a clue as to the difference between a trilby and a fedora. Thank you for your illustrations.

    I have a more basic problem. I have a huge melon. Size 8 (at least), so I have difficulty (a)finding a reasonable selection and (b) some idea whether a particular type of chapeau looks good or stupid on my head.

    Know of a good “big head” hat shop? Thanks.

    Jack L – Phoenix

  10. can you please explain the hat called trilby,how did this hat get the name.

  11. Thanks for the question, Alfred! When compared to a fedora, a trilby hat has a narrower brim, which is snapped down at the front and slightly turned up at the back. It also has a shorter crown.

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