Gentleman Scholar

On Lid-Flipping

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

Troy Patterson.

Troy Patterson

Photo by Christina Paige

Please send your questions for publication to (Questions may be edited.)

Dear Gentleman Scholar,

Hats, thankfully, are back in, and I have an ever-growing collection of various styles and sizes (many vintage). When should one remove one’s hat, and why?


All Agog in Amsterdam

Dank u wel, dear reader, and check out this coincidence: The Gentleman Scholar last purchased a vintage hat while visiting your fair—or, OK—your partly cloudy city. It was a black rabbit-fur ushanka with the symbol of the Soviet Army stitched into its lining. He found it on the afternoon of Dec. 31, 2002, and lost it later that night not far from the Oude Kerk, after a purse-snatching gang decided to diversify its efforts. So here is one answer to your question: Remove your hat whenever walking through a red-light district on a night of ritual mayhem. Consider it a show of respect for local traditions of scoundrelism.

The most complete elaborations of hat-removal etiquette are, like a Louis XIV tortoiseshell-veneer clock case, antique and baroque. The established protocol of doffing and tipping is largely obsolete. Consider, for instance, the directive (h/t Glenn O’Brien) to remove your hat when stopping on the sidewalk to talk to a female friend: What if you’re wearing sunglasses? It is clearly more important and most respectful to lower the shades than to lift the lid, and to attempt both maneuvers at once while administering a bise and trying to do something about your hat head is manifestly ridiculous. Moreover, the old guides tend to waste ink on the nuances of removing a hat to acknowledge a superior. Now, that kind of thing might suit the temperament of our letter writer, who may feel obliged by accident of birth to bow before his king, but it looks like a load of haberdashery balderdash here in America, where the whole idea is that we pretend to be an egalitarian society. I have Friends who’ll back me up on this: Thy need not defer to hierarchal ideas of “hat honor.”

The best reason to remove your hat while out of doors is to show reverence for the symbols of a country that guarantees its citizens the freedom to look down on anyone at any time. Americans should always remove their hats for the playing of the national anthem and for ritualized displays of the flag.

The best reason to remove your hat while indoors is that you are indoors, duh. The general rule is that you should take your hat off while you are inhabiting any room designed for people to sit comfortably and stay a while. Off the top of my head, I can conceive of 10 major elaborations on this principle.

  1. You should remove your hat when at a dining table, especially in a private home or while being waited upon.
  2. You may disregard rule No. 1 if you are a college undergraduate, particularly if the hat in question is a dirty white baseball cap worn backward, and most especially if the hat advertises the school’s lacrosse team.
  3. You may disregard rule No. 1 if you are seated outside at brunch, but only after giving careful consideration to the temperament of your companions, the tone of the establishment, the angle of the sun’s glare, the size of your bald spot, and the intensity of your hangover.
  4. You should note that rule No. 1 regards sitting at a table. If you are seated at a diner counter or at a bar, standards are looser.
  5. You may leave your hat on while seated at any indoors athletic event, but use discretion in choosing the right style for the occasion. A porkpie hat suits a boxing match well; a beer helmet at a gymnastics meet, less so.
  6. You should remove your hat while seated for an evening of theater, or any other entertainment, such as a political debate or town-hall forum.
  7. You may leave your hat on in a nightclub, especially if you are kind of a douchebag.
  8. You may leave your hat on whenever you like if it is an immaculately clean Stetson in very good condition, but only if you know how to rope a calf.
  9. You may not wear a yachting cap inside of a yacht club unless the commodore of the club temporarily designates a portion of the indoors as “outdoors” for the express limited purpose of effecting a ceremonial exchange of salutes.
  10.  You may disregard rule 9 if you are not wearing a shirt, but only on a Village People theme night.

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.