I decided to try another one of my idea as it might just be a better way of capturing the essence of my chosen cities and it's people - not focusing on any particular aesthetic styles yet - just placing elements down and playing around with different compositions to see which would make more sense and look more visually appealing:
I tried to think about and use simple shapes in these, but I'm still not sure if I'm putting too much information in. If I'm being too detailed and/or complicated with them.
Because I'm still not used to Illustrator and still not that confident with the pen tool, I can't predict how easy or quick it'll be to turn something like this into a fully finished, vector image - Not sure if i should just play it safe and go really simple, or take a risk and leave it like this..
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