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A guide to wearing gentleman’s hats

The art of wearing a gentleman’s hat is one that men should be familiar with. There was, after all, a time when a gentleman wouldn’t leave his home without one, but this rather staid convention is well and truly behind us. Nowadays, modern gentlemen wear a hat through choice rather than necessity and as a result, the etiquette that was once second nature to these men has deteriorated.

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We have, in recent times, seen a mini hat renaissance within menswear. This can largely be attributed to popular TV programs Mad Men and Boardwalk Empire, and men are beginning to appreciate the added gravitas a gentleman’s hat can provide. If you too are thinking of enlisting in the oft-intimidating world of hats then you may want to consider some of the following tips.


Before reading up on the rules of hat-wearing, you should first know your trilbys from your fedoras. Here are some hat styles to consider.


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This is the style you’ll see Mr Draper donning in Mad Men. Perhaps the most wearable today, the trilby features a short brim which curves subtly up and around towards the rear, and points slightly down at the front to shield the eyes from sunlight.

Lock & Co Madison Trilby, £225 from Lock & Co


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Typically paired with a sharp suit in the city, the fedora is slightly more formal than the trilby. It features a wider brim and is slightly taller, giving it a more dominating appearance. The fedora is often associated with the mob scene as it was favoured by Al Capone, Charlie ‘Lucky’ Luciano and Meyer Lansky, among others.

Bates J-L Fedora, £450 from Bates Gentlemen’s Hatters


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The bowler (or coke hat) is a traditional style originally designed by William Coke in 1849. It’s a hard hat with a short, rolled brim and a thin grosgrain band.

Bates Bowler, £295 from Bates Gentlemen’s Hatters


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Favoured by none other than Sir Winston Churchill himself, the Homburg is a strictly formal hat, best worn with evening wear.

Lock & Co Homburg, £265 from Lock & Co


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On the other end of the spectrum, the flat cap is one of the least formal of traditional men’s hats. Usually made with a hard-wearing yet soft fabric such as tweed, the flat cap is as versatile as it is practical.

Lock & Co Tweed Flat Cap, £95 from Mr Porter


Like many things in life, hat-wearing comes with its own set of specific rules. We are not saying you should religiously stick to these on every occasion, however if you’re attending a more formal event then you will be expected to abide by them.


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It’s generally accepted that a gentleman should remove his hat when indoors. There are few exceptions to this rule, unless you’re in a pub or lunch-time cafe in which case you can get away with it.

Outdoors is when things get more complicated though. A gentleman should remove his hat when he is being introduced to someone, or when he is saying goodbye to a lady. These notions have been in place for decades and your grandfathers and their grandfathers would have followed them, so you’d be rude not to.


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When wearing a hat was essential practice, tipping it was important business. It was and still is a way of displaying thanks or acknowledgment, and is therefore considered very polite, although it is usually only done to a woman. A gentleman should tip his hat when a lady thanks him or in an instance when a subtle apology is needed.


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This is not a rule so much as a necessity. If you don’t wear your hat with confidence then you simply won’t be able to pull it off and it won’t look good. Look to the black and white films of the ‘40s and ‘50s for your inspiration and if in doubt, just pretend you’re Cary Grant.

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