I think the best kind of a simplicity is the kind that honors beauty. I think if you had a Venn diagram you could have one circle that says "Simplicity" and the other says "Beauty" and there may or may not be a lot of overlap.
For instance, two examples:
Example #1:
I LOVE the kinds of micro-homes that Tumbleweed sells, or like the kind bae posted on.
But I've also seen micro-homes that are shacks.
Both simple, but I'd live in one, and would no way live in the other.
Example #2:
In my permaculture class we saw a video of a community space that a group had turned into organic vegetable beds. Awesome, right? It was.. but one of the class members, who had more of a "gardening" orientation, commented that it was great, but wasn't very beautiful. It was kind of scrappy, and random. (I guess a "beautiful" community garden would be designed with more aesthetics in mind--with neat gravel pathways, orderly raised beds, etc.) The permaculture teacher's response was "Permaculture asks you to see beauty in a different way."
So, what does your Venn diagram look like?
When do you sacrifice beauty for simplicity? Simplicity for beauty?
And when do the two intersect?
What examples can you think of that are in the overlap?
And as my permaculture teacher suggested, has your personal aesthetic changed in your simple living journey?