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Today, it is considered borderline heresy to suggest the Yankees make any sort of changes to their uniforms. Other than on Player’s Weekend, you probably will not see the team wear anything drastically different than the pinstriped home jerseys and the gray away jerseys.
However, the Yankees did not have pinstripes on their uniforms until 1912, and the change did not become permanent until 1920. The plain road grays didn’t become normal until a few years after that.
The story of why the Yankees decided to wear pinstripes isn’t actually that interesting. In fact, the (eventually permanent switch) to the navy blue pinstripes in 1915 was the least interesting thing to do with the change.
One theory that gained some traction through the years was that pinstripes are slimming, and the Yankees got them to help Babe Ruth look fitter. That’s not true, as Ruth didn’t become a Yankee until 1920, which as you can figure out if you read the first couple paragraphs, was after the addition of pinstripes.
The real answer is just that they were a fad in baseball at the time. The Giants had begun wearing them, and the Cubs had started the trend a few years before. The Yankees debuted the pinstripes in black in 1912, but they went away after that year. The Yankees brought them back in navy blue in 1915, and they’ve been there ever since.
Pinstripes were also introduced on the road uniforms in 1915, but, uh, those did not stand the test of time.
Here is the description of them from the reputable SportsLogos.Net:
NY in blue interlocked on a grey jersey with red, green, and blue pinstripes.
No seriously, that is what they wore.
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Not much information on exactly why this choice was made is available. Shockingly, the multi-colored pinstripes lasted just one season. They were replaced by more understandable navy blue pinstripes on the gray uniforms. Eventually, the pinstripes were dropped, and the road grays have just had “New York” or “Yankees” on them in various fonts ever since.
Now onto the other weird thing about the 1915 uniform change.
Nowadays, a ton of the uniforms used end up getting sold. I’m sure if you look hard enough, you can buy a game-worn Pete Kozma Yankees jersey somewhere. However, the sports collection industry then wouldn’t have even been close to as big of a thing as it is now, if it even existed.
So, what would you do with old jerseys in 1914-15? Naturally, send them to prison.
According to New York Times articles from then, the jerseys were packed up and sent to Sing Sing prison so they could be work in an inmates league. There is something very 1910s about an inmates baseball league. Something tells me, sending old uniforms to prisoners is not a regular occurrence today.
The Yankees have worn pinstripes since before any of us were born. (Apologies if there are any 103 year olds reading Pinstripe Alley.) They have become classics and aren’t going to change.
There is also a small part in all of us that probably wishes the Yankees still had red and green pinstriped road uniforms though.
Sources
https://www.snopes.com/fact-check/babe-ruth-pinstripes/
http://www.sportslogos.net/logos/list_by_team/68/New_York_Yankees
https://www.toddradom.com/blog/the-1914-yankees-uniforms-were-sentenced-to-sing-sing-prison