When is it appropriate to wear an Ascot Tie?

I’m wondering when is it fine to wear one because I’m trying to pull off an original look for myself. I’m also asking what can I pair it up with, the idea in my mind is wear it casually with a dress shirt sleeves rolled, dark vest, dark blue jeans and leather boots or even the same on the bottom and just wear it with a simple dress shirt. I’m not sure if that look is appropriate for an Ascot Tie, thanks in advance.

How Do You Tie an Ascot?

I love pocket squares and Ascots. These are somewhat lost on most guys but a really cool & distinctive element. Ascots are not always appropriate but often work well when dressing with Jean and a blazer but want to “formalize” the neck area. I often use them with suits and have a variety of thing silk scarfs that meet semi-ascot criteria.
Do you have any suggestions for tying ascots outside of the traditional? Do you wear Ascots or silk scarfs as a tie substitute? What can you suggest along the silk accessory front? I do not want to be taken for a British dandy but also like to have my freedom in this type of accessory.