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When Did Footballers Stop Tucking There Shirts In?

I think the change happened when the tighter fitted shirts incorporated lycra/elastin type materials in them about 15 years or so ago. My old Everton shirts from the early to late 90's all feel like they are made from 100% polyester & would survive 20,000 years buried in a hole. They also feel like you're wearing a green house.
The current breed are far more breathable, thinner but stretchier which also emphasises a shirt being pulled which is probably a deliberate design feature.
 

Some referees in my local league used to enforce the tuck. You knew you weren't getting away with any shenanigans in those matches.

To answer the OP, I'll put a date of November 23rd 2004 as the date that untucks first exceeded 50%
Yeah it was a booking or fine otherwise in the Bexley C division.
 
Maybe it's an age thing, but in the 1980s the "style" was the opposite: shirt flopping outside the shorts in the maverick fashion. That's why FIFA brought in their silly "tuck in your shirt" rule for Mexico'86:

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