Editor’s note: As an etiquette guide, this article is based on opinion. It’s goal is to create a standard.
When we look at the manliest men in history, many of them wore hats. Teddy Roosevelt, Wyatt Earp, and Frank Sinatra all wore hats frequently. Why then have hats fallen out of favour? I can’t give you an answer because there’s no good reason for it. So let’s put our hats back on and exude the class the fashion world has been trying to extinguish and start wearing outfits that look well thought out and finished.
It’s not always appropriate for a gentleman to wear a hat. He must never wear one when in an office, home, or church, when eating a meal, or for prayer. When coming or going, or in any other indoor space, it’s at his discretion. A gentleman can also use his hat in greeting, but I’ll talk about that in other article. Most importantly, a man should always wear a hat if it’s appropriate.
Like all men’s fashion, subtlety rules in hats. A man’s hat should be mostly neutral colours. A colourful accent piece is fine so long as it doesn’t clash with the rest of his outfit. More colourful and elaborate hats should be kept to casual outfits, where the distinction between men’s and ladies’ hats begins to blur.
Some good hats for a gentleman to have in his wardrobe are fedoras, homburgs, top hats, bowlers, and flat caps or anything along those lines. Trilbys have become associated with some pretty unmanly boys and and classless women, so they’re best avoided.
Ladies’ hats can be far more flamboyant than men’s, just don’t start looking like the Chiquita Banana lady. When it comes to colour, a lady’s hat should at least complement, if not, match the dominant colour in her outfit. Pill box hats and sun hats are good go tos, although sun hats are fairly casual. Fascinators, although not technically hats, are also a great option to go with more formal outfits. Unlike gentlemen, ladies generally only remove large hats when coming indoors, and can wear their hat all day, but wearing a more arranged hairstyle in place of a hat is also acceptable.
When we get into casual hats it becomes acceptable for men and ladies to wear the same hats. Large or flamboyant hats should be reserved for ladies. Baseball caps are very popular casual hats but they should actually be reserved for athletic contexts. Flat caps should be reserved for men and what’s formal for one gender is not casual for the other. Western hats should be reserved for western themed events and activities like ranching and horseback riding, unless you live somewhere like Texas, Arizona, or Alberta. One thing that’s crucial to remember, any branding beyond a maker’s mark expresses a strong association or affinity, so don’t wear any logo simply because it’s fashionable.
Cultural & Uniform Headdress
If you come from a culture with a strong association with a specific style of headwear then go ahead and wear it in accordance with its traditional etiquette, even if it conflicts with typical etiquette. If you’re authorised to wear a uniform that includes headdress, then do it in accordance with regulations, but never wear obviously uniform headwear if you shouldn’t wear the whole uniform.
You may be wondering what hats I wear, and when I wear what. So, here’s what I have and what I plan to get.
What I Have
US Army surplus camouflage patrol cap (street clothes)
Charcoal grey flat cap (casual)
Black fedora (informal)
What I Want
Grey homburg (evening semi-formal)
Black bowler (daytime semi-formal)
Black top hat (formal)
Grey fedora (casual)
Royal Canadian Navy uniform headdress
Black and brown cowboy hats (practical attire, specifically riding)