Would you wear something like this to a casual business setting or on a date? I was thinking to match it with VT tie or an orange pocket square. But the red in the jacket appears to be lighter than maroon.
No. Too much pattern and I don't like matching colors. I'm not a fan of that tie. I'm certainly not a fan of that tie as paired with that jacket.
If you're going to wear a tie, I'd recommend a solid color, perhaps navy. Perhaps a knit weave to keep it casual. Or perhaps no tie at all. Some may say that's heresy but with a sport coat, I find it acceptable.
As for a pocket square. Again, keep it simple; white with a TV fold.
I love Isaia but they tend to employ big, bold patterns and colors. You don't want anything else you're wearing to have to compete with it. It's a fine line between stylish and clownish. Learn that line.