So I have a dark charcoal suit jacket with subtle dark blue pinstripes. I may want to wear this in a casual setting. What are the odds that this works?

I am thinking of wearing it with a pair of dark guess jeans, a white logo tee, and my black leather casualish shoes. Would this be the correct idea behind a successful outfit? How would I tell if this [censored] was working or ridiculous? Feel free to inquire about any missing details or if I have "X" in my wardrobe.

Also, I basically either put product in my hair to make the ladies love it or wear a red sox hat. I assume that I have to do the former and not the latter with this look?

Perrier