If I attempted to fill in the blank, I think he might have said something like:
"Looking back I wish I had gotten this hat in black too, it looks great on dude."
Ok he probably talks nothing like this, but the statement is viable.
The overall silhouette of his look really works, the hat fits well and looks great on him. Having it in another color like black would give him at least two things:
- Ease & Time - He already knows this style looks good on him and it fits well. It's an effortless selection for him. "If it's not broke then don't fix it, just get it in another color"
- Options - Classic black goes with most, he can probably where it with several looks in his wardrobe.