I think he means that it was put together with thought in mind as opposed to somebody who through things haphazardly together. You can usually distinguish the two my looking at the other items in the outfit and how refined they are. For example if he was wearing square toed shoes and pre-faded jeans.
FWIW, I don't think the tie works with the jacket.
Yes, if we know anything about people who spend gobs of money on clothing, take and upload pictures of themselves every workday to a men's clothing website, and sell millions of dollars worth of men's garments on eBay, it's that they are haphazard with what they wear.