Shitty Flag Thread - "Lets add a Palm-Tree riding a horse on our city flag!"

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The flags themselves aren't really that dumb granted. However, during multiple Chinese civil wars throughout history, the various warring factions had a tendency to always want to use yellow flags in order to model themselves after Shi Huangdi. This would often times cause confusion on Chinese battlefields, as the difference between your army's banner, and the enemy banner might be just a slight difference in text.

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Original flag of West Virginia was double sided with the seal on the back and a pretty bushel of mountain laurel on the front. It's very nontraditional and impractical in the real world because it was hard to print and the symbols bled through on each side, but I kinda like the design tbqh.

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A proposed flag for India from 1904, as seen in an Anglo-Indian weekly. The dark blue band represented Hindus and Buddhists, the green band represented Muslims, and the light blue band represented Christians. The vertical purple band on the left side contained the stars from the Orion constellation, which represented the provinces and states. The surrounding red border symbolised India being kept united and whole by British rule.[13]
1920px-Proposed_flag_of_India_(1904).svg.png
 
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