What A Riot! That Guy Is Still Wearing His Straw Hat

By Marilyn May
Milford History

A poster for Straw Hat Day.

Almost everyone knows about the fashion faux pas of weaing white after Labor Day, but breaking that tradition never caused a riot. There was a time 100 years ago, however, when men wearing straw hats after Labor Day actually did cause riots.

Sometime in the late 1800s, seasonal fashion rules demanded that Straw Hat Day was May 15, the first day to don your new straw hat. You did not wear your straw hat before that day, but more importantly, you had better take it off when straw hat season ended. Hats had to go – go in the trash, get stomped on, be torn apart, thrown to the pigs for food or any other creative way you could think of to get rid of them.

In 1900, the day to throw the old chapeau out the door was Sept. 15. Later, the last straw for wearing straw hats became Labor Day, the day when that season’s old hats just could not be worn.

Then the fun began. An article in the Sept. 16, 1900 edition of the New York Times recounted what happened at the stock exchange: “Just because it was Sept. 15 some of the brokers on the Stock Exchange wore their straw hats once more in order to get them smashed, and they were not disappointed. The ostracized hats lasted about fifteen minutes after the opening of the Exchange.”

It was common for teens to ridicule men who wore straw hats “out of season.” That led to a tolerated tradition that allowed teen boys on the streets to knock off someone’s hat and stomp on it. It was one thing when a bunch of stockbroker colleagues purposely wore straw hats to work knowing that fun would ensue, but it was quite another case when unsuspecting men just walking down the street had their hats knocked off and smashed. One year this prank escalated into violence.

Then the riot began. There came a day in September in New York City when newspapers reported on the “The Straw Hat Riot of 1922.”

A New York Tribune headline read: “Straw Hat Smashing Orgy Bares Heads from Battery to Bronx.” The paper also reported: “Stores do thriving business, but many youthful marauders are arrested and seven are spanked at station by irate parents.” They were spanked by order of the lieutenant at the police station desk.

The riot was really a series of riots that lasted eight days. It started when some youthful hat-checkers stomped on the hats of dock workers who started to fight back. A brawl broke out that held up traffic on the Manhattan Bridge. Police arrested many, but fights broke out again the next night when gangs started snatching hats along Amsterdam Avenue and in many other parts of Manhattan.

Some men wearing hats who resisted were beaten and many were hospitalized. Reports cited that 1,000 “hoodlums” were involved, but because most were under age 15 they were not arrested.

In some years, newspapers would print warnings two days ahead of time to remind men when straw hat season ended, and to suggest they switch to felt or silk hats.

How Straw Hat Day started and how the specific dates of its season were chosen is not known, but it is suspected that hatmakers started promoting the idea to sell more hats. Most shops just happened to be stocked with felt hats that fashion dictated should be worn the day after Labor Day. Haberdashers stayed open late for the sudden rush on hats. Come spring, there would be advertisements reminding men to get their new straw hats by May 15, and on it went.

These were the days when no man conscious of class would even think of stepping out of doors without a hat. According to fashion writers, the practice of always wearing hats began to decline after World War II, when men were tired of military uniform hats and steel combat helmets. Today, however, ads can be found for Straw Hat Day 2022 – isn’t that a riot?

At one time, manufacturing straw hats was big business in Milford. In 1852, Elisha Flagg and Nathan A. Baldwin opened a straw hat factory on Factory Lane. It was touted as one of the first of its kind in the country. At its peak it employed 700 laborers who made “thousands of dozens” of hats working with straw in rooms lit by daylight and candlelight.

In 1866, the company came under the management of the Milford Straw-Sewing Machine Company with Baldwin as manager and treasurer. Then in 1880 Nathaniel S.W. Vanderhoef, who at that time was making most of the straw hats in New York, leased the Milford factory. By 1888, workers were making straw matting under the name of the Mitchell Manufacturing Co. Inc. and Baldwin continued his work as treasurer. He retired in 1892 and spent his last years traveling abroad.

The Works Progress Administration book, “The History of Milford, Connecticut” tells us that “Straw hats were made in Milford until after the World War (I).” In 1920, the Croft & Knapp Company purchased the Factory Lane building, but in 1925 moved its straw hat business to Norwalk and its felt hat business to New York City. Then the company returned to Milford in 1927 citing poor labor conditions elsewhere.

Imagine how many thousands and thousands of hats were made in Milford and then destroyed after Labor Day. That practice is probably one reason why the Milford Historical Society has yet to acquire even one straw hat that was made in Milford, a town that certainly knew about May 15, Straw Hat Day, and Sept. 15 when it was time to take those hats off.

Marilyn May is a lifelong resident of Milford and is on the board of the Milford Historical Society.

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