^Exactly thisI usually match the jacket to the outfit I am wearing that day
BUT
Some days I want to wear a certain jacket so I match my outfit to said jacket
I think a very related question to this topic would be:
What do you usually base your outfit on? The jacket? The pants? The footwear?
Which part of the wardrobe dictates the outfit of the day?
My honest answer would probably be something like 60-70% footwear and 30-40% jacket.
I came into "menswear" or style considerations or the leather world in general through the footwear door, not the leather jacket door.