October 1995 SpinSheet column on Mt. Gay red hats reads like a time capsule.
As we celebrate 30 years of publishing SpinSheet, we dug into our archives.
Early readers may remember the “Ask the Spin Doctor” column. Here, in an entry from our second issue in October 1995, the Spin Doctor opines on Mt. Gay red hat etiquette:

Dear Spin Doctor, I am relatively new to the sailboat racing scene, and I received my very first Mt. Gay Rum hat at Mt. Gay/Yachting Annapolis Race Week last month. I would like to know more about the care and feeding of a Mt. Gay hat. I am also curious about any etiquette concerning the hats. Now that I have one, I don’t want to look like I don’t know what I’m doing. ~ Hatful of Questions
Dear Hatful, Congratulations on passing one of the first unofficial initiation rites of sailboat racing. Mt. Gay hats are increasingly difficult to come by, and that only serves to increase their value. Regarding care and feeding: in their quest for the perfect broken-in and faded red hat, many sailors have resorted to artificial means far too hideous to discuss in the hallowed pages of this magazine. The Spin Doctor only respects those who break in their hat naturally. Dip in the Bay and then begin wearing it everywhere. Leving the hat (in a safe place) outdoors for several months or years is also an option. Skip the bleach or any of the cheesy home “speedy break-in” methods that will, undoubtedly, be forced upon you wherever sailors gather.
The question of etiquette is a difficult one, but I have a few simple rules which, if we follow, will make life much easier. First, never, ever, under any circumstances steal another’s Mt. Gay hat. Stealing another sailor’s hat is not only illegal and unethical, but it often leads to the breaking of rule #2 which is: don’t wear a Mt. Gay hat from a regatta you didn’t do. It’s okay if you did the delivery or served as “shore support,” but if you were at your cousin’s wedding during 1991 Block Island Race Week, forget the hat. Getting busted on bogus hats is very uncool.
The Spin Doctor himself has a shelf in his closet loaded with crisp Mt. Gay hats from his younger days. I am planning to break out those hats in, oh, about 25 years or so. Today 1994 Solomons Race Week hats are as common as St. Mary’s College alumni at Marmaduke's but in 2020... way cool.
Note from 2025 SpinSheet editor to the 1995 Spin Doctor—the time has come to break out the hats!