Fashion advice for men: Summer hats and winter hats, and hat etiquette.

When Should a Gentleman Doff His Cap?

When Should a Gentleman Doff His Cap?

Answers for modern men.
June 5 2013 1:38 PM

On Lid-Flipping

When should a gentleman doff his hat? And on what date should he switch straw for felt?

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Dear Gentleman Scholar,

One of your colleagues, Justin Peters, has recently brought to my attention a horrendous crime wave that swept New York City in the 1920s, involving hooligan youth destroying straw hats on the premise of punishing those who wore them late into the fall season. Peters seeks to assure his readership that with the passing of wide-brim hats as a popular fashion, so passes the threat of wild youths vandalizing hats, but I still harbor concerns. As someone who can often be found wearing a woven trilby in warmer summer months, I wonder if there is any current rule regarding the wearing of such hats. Does the Sept. 15th cutoff still apply? Are there other unwritten but possibly thuggishly enforced rules regarding when certain hat colors, materials, or even styles should and shouldn't be worn?


Worried, but not yet mad, Hatter

Thank you for the question, with its invitation to consider whether those hooligans were, in their capacity as fashion critics, more or less tough than Cathy Horyn on Hedi Slimane.

The most established custom sets Straw Hat Day on May 15 and Felt Hat Day on Sept. 15. A rival early-1900s tradition—one closely associated with baseball—ordained that straw-hat season ran from Decoration Day (now called Memorial Day) to Labor Day, when sometimes, after the last out in a doubleheader, the men in the crowd would sail their hats onto the field. I would not chastise a dapper Dan for dusting off his straw hat as early as the Easter Parade, provided he did the dusting with a soft-bristled brush. Nor will I accept chastisement for having worn a straw hat as late as Columbus Day as far north as the Gulf of Maine, to ward of the wilting sun.


It seems to me that the rules of good usage should allow you a good deal of latitude about when to wear a straw hat, taking into account factors such as latitude and global warming and personal steez. If it’s warm enough to wear straw, then do so with my blessing. This column condemns as thugs those who violently enforce arbitrary rules of the style calendar: Excuse me, are those Bugle Boy jackboots you’re wearing?

Is there ever an excuse for violence against headwear? No. Well, maybe. One does sometimes feel the urge to flick a trucker’s hat from a foolish head. But, hey, you never know, maybe the wearer isn’t a poser but an actual long-haul trucker. It isn’t worth the risk. The hat, protecting the seat of knowledge, topping the body like a beacon, is an intimate item in its own high-profile way. It is poor form to ask to try on another guy’s hat. And though I have no qualms about messing with Texas, I would never dream of touching a Texan’s Stetson.

Hats are tricky. Your choice of a straw trilby is à la mode, judging by the early evidence presented on the streets this season. But the trilby, with its narrow brim, does not offer as much shade as one wants when hanging out all day at a music festival. The boater is on that count superior, but it is not so much an everyday piece of headgear as a costume element. Unless a gentleman is possessed of a certain casual balance of dignity and self-irony, he should avoid wearing a boater unless the occasion directly involves the Harvard Eight or Dixieland jazz—but if you want to give it a shot, match it with a blue blazer. The Panama hat, named after the city to which Ecuador importantly exported it, is more relaxed in mood and more convenient to stow: A man can plan to roll up many a Panama. But there is a high degree of difficulty in carrying off the look unless you’re at least 50 years old. It might help if you grow a bushy moustache, or wear it only while going about town with a lady friend who is also wearing a sunhat and perhaps a drop-waist skirt.

The Gentleman Scholar himself favors a straw hat woven elsewhere in the Andes, a Bolivian number that happened onto his head six summers ago. This hat is racking up a stellar performance review on two levels: 1) It earns a lot of compliments; 2) I haven’t gotten heatstroke. I’d suggest that everyone with shoulders broad enough to support a wide-brimmed hat investigate Latin American options, buy an indigenous hat, and spend a lot of time in front of the mirror personalizing the item— preferably tilting its brim for strategic dipping below one eye.