About the shirt and hose matching: it all depends on where he's wearing it.
For a formal dinner aboard ship, I'd say they need to match. White/white, cream/cream, etc.) For going to the grocery store to get your favorite dinner fixin's, it doesn't really matter.
Depending on where you are, what size Hunny is and how much you want to spend, a jacket could be had by the end of this month.
The red and black "checkered" (diced) hose are often worn as formal hose, sometimes worn by 'pipe bands, and are generally available through various websites, some of whom are sponsors here.