Whenever I get a new pair of shoes, I immediately break them in by stepping on the left shoe with my right foot, and the right shoe with my left foot.
It's similar to getting a hair cut, and wanting to get over that odd, uncomfortable feeling.
I wear them on rainy days, while washing the car, an in any situation in a carefree manner and even when they get dirty it's not a big deal to me. I'll brush the uppers from time to time or change up the laces, and before long the leather begins to soften, and naturally mold to my feet.
The more you use something, the more you see it becoming a reflection of your own character, and you begin to feel an inexplicable fondness for the object. The fact you own something like this brings you happiness, and I am drawn to these kind of objects.
When I design products, I consider what is necessary to make something long-lasting, or what kind of things can be enjoyed for a long time. As I ponder those things I also think which materials, dyeing methods, and constructions will aid in that pursuit.
For example, the color in denim will fade over time, but the way in which it fades is dependent upon the wearer's environment and the way the denim is worn. It's the same with vegetable-tanned leather. These materials are highly affected by climates, temperature, sunlight, and the wearer's environment, which is precisely why human character is reflected so well. That metamorphosis is beautiful.
Personally, I enjoy watching this change, and as a creator, it truly brings me joy.