How about something a little atypical: a history of the flags of a fictional micronation
Having been a concept/idea of some kind ever since I was in elementary school, in 6th grade or so I established "Peytonia," a sprawling nation, population 1, with territories including my bedroom at my parents' house, the spare room in that same house, an unofficial claim of Marie Byrd Land in Antarctica, and a similarly unofficial claim of a swath of land on Mars north of Valles Marineris. I've passively on-and-off stuck with it ever since, even if more of an idea than a physical entity. That includes drawing up flags and symbolism!
There used to be MS Paint files of all of the early flags and symbols, but those have been lost to the sands of time, so the 2010-11 and 2013-14 are crudely drawn approximations. The 2012 one is actually someone made for me in high school which I still have, so I dug it out and took a picture. As a basic rundown of each:
2010-11: My family refers to me as "Bug" which is a nickname nobody has any idea where it came from, and nobody outside my immediate family calls me by. So I decided to use the bug (specifically an abstracted beetle kind of one?) as my first concrete national symbol. Like I said, the original of this flag is long gone, so I recreated it from memory. It drove my crazy trying to remember whether I had a black bug or a gray or gold bug, and the black and red may be reversed, but you get the idea. Imagine the crude thrown-together approximation here, but even crappier and more compressed and you get the idea. At this point, Peytonia was no particular government, but best described as a monarchy. Perhaps the strong black and red coupled with self-referential icon of its founder reflect that.
2012-2014: at this time, Peytonia was a "Constitutional Monarchy" and I decided to revitalize the flag accordingly. Yellow was introduced as a national color, and the bug went to the wayside, replaced with the "Giraffe" seal (giraffes are one of my favorite animals, though sadly no giraffes are native to Peytonia), with the checkerboard royal shield, flanked by branch and sword, representing growth and power. The flag shown here was by a high school friend based on my design, she definitely idealized the branch from its original idea whereas I genuinely just imagined it representing the weeds that grow outside in the yard of the house (really). The old English lettering spells "Peytonia" and while hard to see that's supposed to be roman numerals representing the year I was born (not telling that, but I absolutely butchered the numbering and had no idea how it worked so its wrong and barely readable anyway).
2013-2014: I got into the Beatles, became quite an idealistic Micronation leader, and the flag transitioned accordingly. While the previous flag still hung up on my bedroom wall, I designed a totally different kind of flag and symbol. The giraffe was eventually retired as a symbol. Light blue canton coupled with the plain white field symbolized peace. I also began writing music at this time, so the new symbol reflected it: a music note coupled with a peace sign. In all a very weird time symbolism wise for Peytonia, which became a Republic and is still to this day (I even wrote a two-page constitution in 2014).
2017: after shelving my duties as leader and sole citizen of Peytonia for a while, I decided to revisit it once again and give it a simple, clean, unique flag. I reincorporated red and yellow, and the yellow and blue stripes have thinner/more spread out dimensions than most tricolors (I based it off of the flag of Crimea). Early variations had no "~P~" at all, but I decided to add it later to fill the white which looked emptier than a normal tricolor since the top and bottom stripes are wider apart. Blue still represents peace as well as good will, and the gold now represents good and fruitful living.
As a bonus, I included an updated sketch of the national seal that I did during some downtime at work the other day. Since the flag is simplified, I decided to incorporate the classic symbols of Peytonia back into the national identity by way of its seal. The bug is stamped at the bottom, while the shield is flanked by the giraffes. The same "~P~" appears here for continuity with the flag. The proper roman numeral "MMX" appears as well in the banners reading "Est." and "MMX" to represent the proper naming and founding of Peytonia in 2010.