For me, wearing heels evolved in different stages. From an early age (early teens) i was fascinated with heels, loved the shape and appearance. I cant remember when i tried on a pair of heels for the first time but the furtherest memory i have is in the early 90's, trying a pair of heels my friend (she) had lying about. I was lucky as i have small feet so the fit was almost right. I purchased my first pair in my late 20s (late 90's) when i lived on my own. I accumulated a small collection of heels and boots which i wore occasionally when opportunities arose.
Leaping forward til about 6 years ago, wearing heels is basically a daily event for me. The styles have changed a lot over the years, and have a mixed array of styles and colours, but now comfort is the foundation of any pair i add to my collection.