The majority of this topic is largely based upon the musings of David Pye, creator of the bowl at left and author of The nature and aesthetics of design. I'll pull some quotes from the book and just ramble on about what they mean to me; all while I wait anxiously to hear what they mean to you. Hopefully we won't go off the deep end!
I'm probably not the first nor the last to stand on Pye's shoulders and expand on his philosophy, but I'll do it anyways. I just hope you get as much of a good kick out of the book as I do.